Tonight, I’m set to board Singapore Airlines for the longest flight in the world! Perhaps a hot take, but I love a long-haul flight. So, I’m looking forward to the 18-hour and 50-minute journey that’ll bring us to…you guessed it, Singapore! It’ll be my first time, and we have some epic guides set up to show us around. And that’s just the first stop on a two-week trip primarily dedicated to exploring Western Australia. Lots more to come over at on this largely overlooked part of the Land Down Under.

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The week leading up to tonight’s departure has been a bit nutty. A meeting hosted flawlessly by . Lila Raicek’s debut book, The Plunge, launch at McNally Jackson, moderated by Griffin Dunne with a special appearance by artist Karyn Lyons whose striking work graces the cover. Provisioning allllll the things (my fave sport!!!!) at the Union Square Farmer’s Market to curate a pretty little spread for ’s baby shower. A very special birthday dinner for our dear Jenna in the wine cellar at Roscioli. Dancing to The Muses’ set at Jean’s with the girls. Goodbye drinks amid last night’s pouring rain (emblematic of my tears?) for friends before they head off to San Fran. And now, right where all roads lead for me on Sundays—curled up in my bed editing this edition of TSS.

Naturally, I have yet to finish packing for tonight’s departure. I was actually giggling yesterday at the hair salon when my girl was like, “you’re always going somewhere! you must be so good at packing.” Because yes—and also, no? I have my method and it works. But like anything (working out, eating healthy, etc.) you actually have to DO IT for the method to work. And in classic fashion, I can’t seem to get myself to commit to putting the piles of clothes I’ve set aside into my packing cubes.

One thing that will definitely make it into my bag is this fun travel set from my friend Matt, the genius behind creative efforts at Maude. If you haven’t heard of it, this modern intimacy company makes for a fun follow on Instagram. And in the case of this latest travel-themed launch, they’re making sure everyone is ready for takeoff…in every sense of the word.

What a delightful surprise it was earlier this week to see myself on The Business of Fashion homepage. A reminder, I think, that the things we chip away at quietly over time—in my case, writing a weekly letter for so many years and in the process, honing my taste—do in fact compound. I’ve been thinking a lot lately about longevity in creative work, and how much of it comes down to just…staying committed to showing up.

The article, “Not All Creators Convert. Here’s How to Find Those That Do” was reported on by and was partially a commentary on how more niche audiences like mine convert best! Translation: you all actually shop the links I share (!!!) on my ShopMy. Specifically, it was fun to share how you’ve all bought over $10,000 worth of my favorite rag & bone sweatpant jeans. The article is paywalled, but here’s a snippet in case you want to read.

Anyway, a small moment, but one I wanted to share with you here because my Substack community has been such a big part of me finding my stride with affiliate links. THANK YOU, FRIENDS!!

Stateside, two weeks from today is Mother’s Day—a holiday that snuck up on me in the way it always does. Whether you’re shopping for your mom, a grandmother, a friend who just became a mom, or someone who’s simply played a mother-like role in your life, I pulled together a list of gifts that feel elevated but still personal—things she’ll actually use.

Mother's Day Gift Guide

• Sabre Bistrot Spreaders for the mom who somehow makes even a Tuesday night cheese plate feel dinner party-worthy.

• Evermill Spice Rack: counter version or in-drawer version for equal parts practical and aesthetic—a true kitchen upgrade.

• ’s new cookbook, Riviera, paired with a bottle of Ghia is the chic hostess gift that feels super fresh given that this book comes out in just a couple of days!

• Normann Copenhagen craft salt & pepper mill set for a super chic upgrade to your current S&P set.

• Loewe Tomato Leaves Handsoap makes for such a fabulous gift because while it feels indulgent, I promise you there’s no more intoxicating scent to wash your hands with.

• Flamingo Estate Garden Tour Candle, Olive Oil, and Soap Gift Set for a trio that smells like you have a garden in Ojai.

• LED Face Mask for the bio-hacking mom who’s committed to the bit and will incorporate LED into her regular routine.

• TheraBody TheraFace Depuffing Wand for a ride or die item at my bedside when I’m home and in my dopp kit when I’m traveling.

• A shakeplate for lympatic drainage because I swear it has changed how I feel on a daily basis. I use mine for fifteen minutes every morning after working out.

• MZ Wallace Pickleball Tote is perfect for the momma who loves to keep active and look good doing it.

• Infrared Sauna Blanket for the wellness-loving mom who has everything except this, a tool many of my friends swear by.

• Crown Affair Microfiber Towel for something she’ll use every day.

• La Bonne Brosse Mother and Baby Brush Set comes as no surprise from me since I have both a big and small LBB brush but this is the first time I’m seeing them bundled!

• Sophie Bille Brahe tassel velvet jewelry box in burgundy to help her enhance the way she’s keeping her jewels organized.

• Natural Manicure Set for something small, useful, that she wouldn’t necessarily buy herself but will keep in her everyday bag!

• Ember Heated Mug because her coffee deserves better and the idea of never having to microwave a cup gone cold is luxury.

• “Go Ask Your Dad” hat for the mom with a sense of humor.

• Weezie Robe with Embroidery for something personal, plush, and again, something she’ll be able to enjoy everyday.

• Foldable Gardening Seat with Tools and Detachable Tote for the mom who’s in her gardening era going into summer.

• Portable Sonos Speaker makes for an ideal way to have her armed with tunes while she’s pruning her perennials.

• Gardening Organizing Bucket Caddy because every element of gardening can be cute if you want it to be!

Thank you for reading, friends! Given my intensive travel schedule, I don’t plan on being in your inbox next week unless an abundance of time falls into my lap (ha!). But promise to see you in a couple Sundays. xxKD

I felt feral for it all. Relieved to be outside without a jacket, I was struck by the condition that often afflicts me in these conditions: I forgot how to cook for myself. In fact, this past week, I ate out more times than I can even count, savoring new and old favorite bites that deserve their own moment in the sun. The fried chicken sandwich at Empire Diner. The burger and exceptionally creamy vanilla custard at Wild Cherry. The oven-roasted chicken that tastes like Paris at Raoul’s. A scoop of pistachio and cannoli ice cream from Salt & Straw. The shaved brussels sprout salad from Left Bank. The mint chocolate chip smoothie from Sunlife Organics. My favorite lunch for when I’m just a ~littleeee~ hungover: the chicken caesar wrap from Edith’s. The fried artichokes at Hudson Clearwater…actually, come to think of it, I had fried artichokes three times this week, including at Bottino, a beloved spot that returned our request for the check with a receipt showing no amount due, just “THANK YOU!” scrawled in Sharpie.

God, I love New York.

There was real work, workouts, therapy, 10,000+ steps a day, and lots of laundry, too. But for the sake of the letter, let’s talk about what this warm weather did to my psyche…naturally, it had me fixated on summer plans. Or rather, my lack thereof. I became particularly obsessed with how and where I’ll spend Labor Day, a holiday that just so happens to fall the day before my birthday this year.

If you’re new around here, perhaps you don’t know about my birthday trip tradition. Let me catch you up about just how insufferable I am!!!!! Since turning 21 in Barcelona, I’ve made a point to be away on my actual birthday (Virgo much?) every single year. From Sri Lanka to Vietnam to Mallorca to Mexico, I’ve held strong on this shtick for a decade and counting. So, with years and years of recon under my belt, I’ve got lots of ideas about where to celebrate your birthday solo, with a partner, or with a gaggle of friends.

If I’m being honest, for many years, my birthday trip plans have fallen together rather last-minute. But not this year. No, this year, I have a clear vision of the twelve-room hotel in Northern Africa where I dream of waking up the morning I’ll turn 33. So instead of hemming and hawing and trying to line something up via work, I did something unusual for me. I went straight to the hotel’s website, booked and paid in full for our stay, five full months in advance.

Committing to a trip of this caliber when there are soooooooo many other destinations I could choose instead has historically been hard for me. I like to change my mind!!! I like to see what might pop up!! But having something to look forward to—and actually relishing the anticipation of that—feels like progress in a different way.

And it’s exactly this indecisiveness, this constant urge to keep options open, that gave me the idea for this Substack. I’ll never be able to take all the summer trips I dream up (at least not in one season), so I figured I’d feed you a few of them—some from places I’ve visited and loved, others from the ever-growing list currently on my radar.

My credentials for compiling such a list? I’ve worked in the travel industry for more than a decade—and if there’s one thing I know how to do, it’s Euro summer. Naturally, travel is ever-present in what I share here, and paid subscribers to The Sunday Series have access to my travel guides, in addition to my top hotel stays of all time which includes the check-ins around the world that are at the top of my list.

And on that note, the majority of this letter will be reserved for paid subscribers, as I want to make sure those who support my work here are genuinely feeling that value. These recommendations are the result of more than fifteen years of investing in my own travels—and I really appreciate the support that allows me to keep doing so!

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While places like the Amalfi Coast, Capri, Lake Como, and St. Tropez surely have their appeal, I’m not personally in a season of life where I’m gravitating towards these hotspots in high season. To me, going somewhere super trendy during peak June, July, or August dates is just asking to be amongst a heavily American jetset crowd, and that doesn’t do it for me. I mean, if I wanted to wind up at a restaurant cozied up next to a table of my NY neighbors in summer, I’d just go to the Hamptons! No need to trek to Italy for that. So, my Euro summer suggestions are going to be a bit more off the beaten path.

Turkish Riviera Meets Greece—Combine Bodrum and Kos: I turned 30 at Maçakizi Hotel, and my mind wanders to this Bodrum paradise often. I desperately want to go back, and this time, I’d combine it with Kos, a Greek island that you can reach by ferry in about half an hour from Bodrum. I’ve personally got my eyes on Ikos Aria in Kos, which feels easygoing and unfussy. The island is known to be flat and bikeable, unlike many Greek islands, making it ideal for cycling from beaches to town.

Charter a Turkish Gulet with Friends: I looked into booking a gulet boat for the same birthday and know it’s an idea I’ll come back to one day. What makes it so appealing is just how attainable it is, price point-wise—especially when split among a group—without sacrificing any of the magic. Think slow days hopping between hidden coves, long lunches on deck, and the kind of sun-soaked, slightly unstructured rhythm that makes for the best kind of group trip.

A Greek Island Hopping Trio with Athens, Milos, and Sifnos: I fell in love with Athens last summer. We combined a few nights at the Four Seasons Astir Palace Hotel Athens with Zakynthos (loved Lesante Cape and our boat day, but the towns on the island weren’t the most charming IMO), which reminded me how much Greece has to offer. For my next island-hopping adventure, I’d combine the mainland with Milos, where Skinopi Lodge looks like actual paradise, before taking a ferry to Sifnos, where Stamna Sifnos has my eye.

The Car-Free Greek Island Calling My Name: I once read a book set on Hydra (Beautiful Animals by Lawrence Osborne), and the island has been humming in my subconscious ever since. Perhaps what appeals to me most is that cars are banned here, and if you didn’t know this already, I actually don’t have a driver’s license, so this is my literal dream! I’m crushing on Bellevalia Hydra, which sits between the mountains and the sea with just eight rooms.

Marseille over St Tropez: Some of the chicest girls I know are forgoing St Tropez for Marseille and its surrounds. A grittier, more multicultural version of the Riviera, Jacquemus is just one of many creatives hailing from the region—a place that acts as a hub for chefs, artists, and entrepreneurs. Specifically, Tuba Club, located forty minutes from town in a small fishing village, stands out as the cool-kid hotel with its rocky swimming cove and yellow beach chairs that seem to have my name all over them.

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Reporting live from the kind of spring weekend that can’t help but put a pep in your step. Luckily, today’s letter was 85% drafted when I woke up because last night culminated in dancing till 3 am at a Baz Luhrmann-backed bar on the Lower East Side. It was the most quintessential New York night—the kind that reminds me how lucky I am to be in this chapter of life.

This marathon of sorts was my second endurance workout of the day, considering I started my Saturday with a five-mile run in Central Park to see the magnolias and cherry blossoms in bloom! The endorphin high from a sunny Saturday run is like nothing else. In another world, I’d wander over during the middle of the work week for a leisurely walk to see the blooms, but alas, capitalism! Work! So, so much weeeerrrkkk.

I try not to think of this newsletter as “work,” but the amount of time I carve out for it every week says otherwise. I’ve actually been toying with the idea of dedicating an entire issue to how the sausage gets made because I have so many people who ask how I manage it all, but I fear it could be too self-aggrandizing?? If you think an issue like this would be fascinating (essentially, a roadmap on how to make time for the creative pursuit you claim not to have space for), holler. But let’s get into it, shall we?

• What I’ve been watching, reading, and listening to this week

• What I’m buying during the Sephora Sale

• The Vault (Paid Subscriber Exclusive): an honest check-in, one year into committing to consistent strength training amidst a world where everyone is seemingly shrinking

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On the pop culture front, it was a busy week. Aubrey Plaza and Christopher Abbott are expecting a child together, which thrills me in ways I can’t quite explain. A few months back, we saw them while we were also dining at Commerce Inn, and it just felt so right? On that note, Girls fans: we get to look forward to the release of Lena Dunham’s memoir, Famesick, set to hit stands on Tuesday. I’m so hyped! Here’s a fun interview to listen to in the interim of its release…

Reading-wise, I’ve been enamored with Yesteryear by —I was fortunate to get my hands on an early copy and can’t put it down! I assure you this is going to be one of the buzziest books of the year, aided by an upcoming adaptation, in which Anne Hathaway is acting and producing. Otherwise, our April book is Once and Again, Rebecca Serle’s latest, which I read back in December when in Australia. It’s compact and poignant, as all her novels are; Rebecca was a TSS guest when her last novel came out. For me, every book of hers is an auto-buy.

On the streaming front, Friday night, my dear friend Jenna came over, and we watched the Laguna Beach Reunion. It wasn’t as juicy as I’d hoped, but it was fun to watch, if only to reminisce over how differently TV looked 20 years ago!! I’m currently in the midst of rewatching Euphoria in preparation for season three, which drops its first episode today. And on the movie front, this afternoon, I’m headed to AMC to see Zendaya and Robert Pattinson in The Drama, which has been getting divisive reviews. More to come.

Before we dive into the heart of this week’s letter, a special thanks for all your kind notes on last week’s edition, where I dove into some of my favorite pieces in my apartment. I can’t believe I’ve been in my studio for five years now!!!!

Okay, now onto the beauty of it all. No matter how busy life gets, if there’s one thing I’ll always make time for, it’s the Sephora sale. Equal parts restock, refresh, and a slightly dangerous excuse to try something new, this is always a moment to revisit the products I swear by—and the ones I’ve been eyeing. I’ve rounded up the picks I don’t think you should miss below!

All My Sephora Sale Picks

• INNBEAUTY Extreme Cream: this moisturizer is an absolute GAME CHANGER! The perfect weight is something our entire friend group is in agreement on being a must-have.

• Saie Glowy Super Gel: perfect for an instant glow under makeup, even when you have no tan.

• Hourglass Vanish Airbrush Concealer in Silk: I don’t remember life before this magical product. If I could only have one makeup item on a stranded island, this would be it.

• Rhode Eye Patches: I’m in my eye patch era! I keep these in the fridge and love throwing them on in the morning.

• Isle of Paradise Self Tanning Drops: ‘tis the season to start putting these drops back in my daily lather of body lotion.

• Kérastase 8h Night Hair Serum: I put two pumps into my hair every other night. Smells fantastic!

• K18 AirWash Dry Shampoo: what they’re saying is true…this dry shampoo is unlike any other product on the market. Goes on in a light spritz (versus aggressive aerosol) and doesn’t leave a residue.

• Ouai Medium Hair Shampoo and Oui Medium Hair Conditioner: my current shampoo/conditioner combo! Love the weight and smell.

• Tatcha Kissu Hydrating and Plumping Lip Mask: I’m addicted to this! A must before bed to stay hydrated.

• Rare Beauty Tinted Lip Oil: this tint stays on so well. And, fun fact, it was the one Alysa Liu was seen asking for to reapply before she podiumed for her gold medal.

• Makeup by Mario Lip Pencil: last night, I went to reline my lips and we started giggling because all three of us use these same liners. That should be endorsement enough! I love the Rich Mauve colorway.

• Tatcha Rice Wash Skin Softening Cleanser: this has little beads in it to exfoliate, which is so needed on the road.

• Inn Beauty Extreme Cream Mini: as mentioned above, this is my holy grail, and I can’t live without it, especially when on the go.

• Caudalie Beauty Elixir: perfect to hydrate on the plane and keep the skin feeling fresh.

• DedCool 01 “Taunt” Travel Perfume: this is an easy, neutral-smelling fragrance to keep in my dopp kit.

• K18 AirWash Dry Shampoo: again, as mentioned below, this is a must for second-day hair.

• Westman Atelier Bronzing Drops: my friend Jenna endorsed these, and I’m excited to try!

• Armani Eye Tint Liquid Shadow: keep seeing this pop up everywhere and feel it’s time to take the plunge.

• Better Than Sex Volumizing Mascara: another Jenna rec!!

• Crown Affair Microfiber Towel: I’m in need of a microfiber towel replacement, and the girlies seem to love this one.

• Hourglass No. 15 Blush Brush, Hourglass Finish Concealer Brush and Hourglass Foundation Brush: I’ve been in severe need of a new set of makeup brushes, and these ones are widely endorsed as the best.

All My Sephora Sale Picks

And now, the juicy bits. In my first letter of 2025, I wrote about trusting myself enough to own a scale for the first time since I was 19. Back then, my college roommate quite literally confiscated mine because I had become obsessive—stepping on it each morning before my two-a-day workouts, despite weighing nearly 30 pounds less than I do now…and still believing I needed to lose more.

That version of me was three marathons and many personal reawakenings ago. That headspace ruled by insecurity feels both like a distant memory and a version of myself that I can immediately conjure. And for obvious reasons, before delving into exactly what I mean by that, it feels safer to continue sharing behind the paywall.

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To stay on the Easter theme, I had some bunny-shaped dumplings at Red Farm on Friday, and this evening, my dear friend brought coconut and carrot cake from Little Cupcake Bakeshop over for dessert. God, I love a holiday that encourages copious sugar consumption!!! While we’re on the note of food, I balanced out all the carbs with a modified version of this Fresh Shredded Snap Pea Salad with Lemon and Mint tonight—highly recommend incorporating into your spring rotation. Oh, and the squash soup pictured below was from Meadow Lane, which my fellow New Yorkers should know is now on Uber Eats!

Beyond food, I’ve got lots of goodness to dig into with you all in today’s hearty edition, but before doing so, I wanted to do a call back to a letter I shared around this time last year: prompts for a [positive] quarterly review, considering we’re at the top of the quarter. And on the note of The Sunday Series community forever being on a quest for self-improvement, I’ve been beyond touched to see such a warm reception for last week’s letter, “Spring Training Starts Now: a 30-day sprint formula to feel your best.” Sharing it below ICYMI!!

Okayyyy, a juicy one today! Here’s what's on deck in this Sunday’s letter:

• Five years in 450 square feet: how I turned my studio apartment into my sanctuary

• The Vault (Paid Subscriber Exclusive): how I’m tracking on my exact Spring Training Checklist, plus the extended cut of what I’m doing to really dig deep

• The Vault (Paid Subscriber Exclusive): the podcast queue that’s been keeping me listening and learning

In addition to sweet texts and email responses about how last week’s letter resonated, it seems to be reaching a new audience beyond my subscribership here on Substack, not to mention bringing in a wave of new paid readers. If you’re one of them, thank you! Some more on the bits and bobs you get access to with your enhanced subscription below.

Paid subscribers of The Sunday Series unlock an exclusive section of paywalled content in each send, access to the full archives (including Your Local’s Guide to West Village, A No-Gatekeeping Guide to Mallorca, A Mini Formentera Guide, Your Ultimate Paris Guide, Your Guide to Bozeman, Your Guide to Nantucket, 100 Hotels I’m Dying to Check Into, My Holy Grail Rules for an Overnight Flight, 31 Ideas for Your Next Birthday Trip, A Playbook for How to Make Friends As An Adult, and 16 Prompts for a Personal Quarterly Review), the commenting feature on each post, exclusive giveaways, and more. Plus, your support directly helps ensure this newsletter can continue to grow! Subscriptions are $8/month or less than $7/month if paid annually—also known as less than one fancy Starb*cks order. But don’t let me be the one to tell you why you should upgrade! I’ll leave that to a fellow reader…

“I’ve been following your newsletter for the past few months and it’s such a delight! It always makes me smile and I feel like your content is thoughtful and unique every week. I’m glad to finally be able to support you with a subscription.”
– Gina C., paid subscriber of The Sunday Series

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This weekend, Facebook kindly reminded me that I moved into my West Village apartment five years ago. Naturally, I fell down a memory lane spiral (read: my incredibly detailed camera roll) and started texting my dad photos from that April weekend in 2021—the one when we were still wearing masks while traipsing through Home Depot. Below are some photos (including the contents of my wine-filled fridge on move-in day) for a general sense of vibes at the time.

While this wasn’t my first time living alone, it was my first solo apartment in New York—let alone in my dream neighborhood—so moving in felt like a very big deal. From the moment I signed the lease, I had a clear vision for how I wanted the space to feel, and in turn, had already sourced much of the furniture and fixtures before even making that fateful first climb up to my fifth-floor walk-up. Within a week, my mom came to visit, and between various shopping missions, we wallpapered part of the apartment to carve out a real sense of separation in the dining area.

When I look back on photos from my space taken five years ago versus today, there are some clear differences: I’ve upgraded my couch, for one! I’ve flipped my rug. I killed a plant that I tried so hard to make work, but unfortunately, I don’t get enough natural light to keep many things alive in here. I’ve FILLED my bookshelf. I’ve swapped out my duvet, bed sheets, and curtains.

But ultimately, the vision has remained the same: this is my sanctuary. My space to come home to between trips and feel like I’m surrounded by all of my favorite things. Namely, flowers and candles. ALWAYS fresh flowers…and more often than not, a taper candle burning (day or night).

In case you’re in the market for some home goods, I’m sharing a rundown of the items that have made all the difference to my daily life as I’ve made this cozy 450-square-foot studio home. I’m recapping everything from furniture to glassware to organization that can help you optimize apartment living. Plus, most is also linked on my ShopMy!

My Apartment Links

• Round 48” Walnut Pedestal Dining Table: the very table I’m writing to you from right now! She’s held up so well, zero regrets.

• Chairs: the exact make of my dining chairs is also no longer in stock, but interestingly, Anthro is carrying the same chair in a funky print I adore, in addition to these options. Or, if you’re looking for counter height, they have my same colorway and style.

• Renter-friendly wallpaper: the corner of my place that I’m easily complimented on the most is my peel-and-stick wallpaper. One day, I’ll have de Gournay, but for now, this is a solid enough hack! It’s been up for five years and still looks like it did the day we installed it.

• CB2 Couch: my exact couch (Strato 80” Camel Velvet Sofa) is no longer available, but if I were shopping for a new one today, I’d be all over this similarly colored curved option, or this gorgeous green option.

• Acrylic coffee table and bedside table: the specific vendor I purchased from on Etsy is listed as ‘taking a short break,’ but I’d highly recommend looking around on Etsy for something similar if you want the acrylic look.

• Anthropologie Primrose Mirror: by no means am I claiming to be creative in recommending one of the internet’s most adored mirrors, but I stand by my choice to splurge on her. Lots of different sizes depending on what you need!

• 40” Bar Cart: I was sooooo happy to see that not only is West Elm still selling this tiered bar cart, but it’s 21% off at the moment. Run, don’t walk!

• The Frame TV: I didn’t have this baby when I moved in but I regret waiting even a moment to get her! Easily the best tech investment I own.

• Ornate gold frame for Frame TV: A Frame TV is nothing without…a frame. While Samsung has options, respectfully, ew? This gold baby is the anchor to my gallery wall!

• My gallery wall: these will, for the most part, be impossible pieces to link since I’ve acquired them all over, but several are from Gray Malin, which is always a great place to start when perusing wall art.

• Boll & Branch Sheet Set and Boll & Branch Towel Set: life has quite simply been better since upgrading my sheets and towels. Can’t recommend enough!!!!

• Jolie Filtered Shower Head: feels like a no-brainer to filter out chlorine and heavy metals from your daily shower, just wish I’d gotten mine sooner.

• Velvet Curtains: I didn’t get these until I was in my place for a bit, but now I can’t imagine not having them! Mine are the dark olive colorway in 48"x84".

• Hatch Alarm Clock: you guys have heard me raaaaaaave about this and I really do mean it when I say this alarm clock has changed my life.

• Steamery Steamer: another newer edition to my space, but I wanted to add it because it makes such a noticeable difference to my daily life. I had had this steamer provided in a number of hotels until I finally decided I needed the same one at home. LOVE!

I always giggle when people ask if I “even cook.” I certainly do, and all in this gloriously compact kitchen!!

• De’Longhi Coffee & Espresso Maker: this is one of the items that’s been with me since month one here, and I can’t imagine daily life without her! I influenced my sister to get the same when she moved into her new house, and she’s an equally big fan of the variety between being able to oscillate between drip and espresso.

• East Fork Bowls: a more recent upgrade, and I can’t say enough great things about how fabulous these bowls are! Very multipurpose, from everything to salads to soup.

• Handblown Glass Cups: also from East Fork, I love the weight of these, along with the neutral colors

• Plates from Morocco: obviously another ceramic element that I can’t link, but treasure! More about the story behind them here in .

• Espresso cups from Turkey: nooo links here (obvi!) but these spark daily joy. A reminder when you’re traveling, just buy the fragile thing you love and figure out how to get it home safe!

• Knives from France and Japan: once again, no links, but I’m always so happy to collect home goods when I’m away. Last fall, I nabbed some special tomato, bread, and butter knives from France, and this past month, I upgraded my kitchen knives in Japan. So worth it!

• Sets of Bookshelves: looks like the finish I have isn’t in stock anymore, but there are two other options avail via this link. I have two of these that sit side by side and as you can see from the pic, they hold a lot of books!!

• Stacks of Assouline coffee table books: these are split between my bookshelf and dresser, but I have eight and counting—they add such fun pops of color to the apartment.

• Stackable Drawers: this is hiding in my coat closet, and I use it to keep all my baseball hats, packing cubes, and the plethora of canvas totes I’ve acquired sorted.

• Over-the-Door Shoe Organizer: for obvious reasons, this is essential to apartment living!

• Under the Bed Boxes: and because there’s never enough room to shove all of the out-of-season shoes out of sight, these are musts. I have four under my bed.

Ahhhhh are you still with me? Yay! Time to track how I’m pacing with Spring Training.

Last Sunday, I shared my daily non-negotiables as a part of my personal Spring Training plan.

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Actually, speaking of the other side of the world, a month from today, I’ll be boarding the longest flight in the world: New York to Singapore. That means these next few weeks feel like a runway to tighten things up before travel inevitably (albeit temporarily) undoes all the practices that make me feel my best. And it’s exactly this kind of timeline that motivates me to double down on routine while I’m able to cling to it.

That said, I’m treating April as “Spring Training.” That is, a defined window to get back into tip-top form before the chaos (and endless rosé) of summer arrives. Shoutout to Tinx for putting a name to this season and my TikTok algorithm for putting me across a “sprint month” concept. Collectively, I’m lifting bits from both to build my own version. Not a transformation—just a recalibration.

And in today’s edition of The Sunday Series, I’m sharing the framework I’m using. It’s intentionally simple, entirely customizable, and built to help you actually stick to something.

• Your Spring Training framework

• The Vault (Paid Subscriber Exclusive): my exact Spring Training Checklist, including links for my supplements and more

• The Vault (Paid Subscriber Exclusive): my go-to sweet and savory breakfasts that are each 35g+ in protein

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It would be a grave mistake to try to “fix” everything about your routine at once. Spring Training works because it focuses on fundamentals—so pick a few things that move the needle most for how you feel. Yours may be more career or family-focused, but mine are primarily all in the realm of health.

For me, the pillars of my Spring Training include:

• Maintaining my sacred morning routine: being out of bed by 6a and getting movement in early, followed by a habit stack with 10 minutes on my shake plate

• Daily movement: achieving my daily step goal and weekly quota on strength workouts

• Nutrition and supplements: cleaner, more consistent protein intake

• Sleep, Sleep, Sleep: protecting 7h+ it like it matters, because it does

But here are some others you could consider:

• Relationships: being more intentional about who you see and how you show up

• Social life: saying yes more—or being more selective, depending on the season of life you’re in

• Career: focused blocks of deep work, finally sending the pitch, asking for the thing

• Creativity: writing, reading, making something that isn’t tied to output

• Personal admin: getting your life in order—finances, inbox, appointments

• Home: refreshing your space, finally organizing the drawer, making it somewhere you want to be

• Style: editing your wardrobe, getting dressed with a bit more intention

• Learning: taking a class, reading more, going deeper on something that interests you

• Travel Planning: locking in the trips that future you will thank you for

• Community: showing up for your people

Aiming for daily perfection is where most of our best intentions die. We feel like three days into something, we’re already failing, so we throw in the towel altogether. Instead, I’m aiming to track my habits as a weekly total—something I can flex in real time.

For example, with movement here are mine:

• Create a weekly step goal (mine is 70,000). Miss a day? Redistribute. Go over one day? Great, now you’ve banked steps for a day later in the week when rain sabotages the best of ambitions.

• Strength training 4x a week: I’ve talked before about how consistent strength training has been SUCH a big unlock for me. To stay accountable, in April, I’m scheduling a 45-minute weight-lifting class at least four times a week.

• Filler cardio days x 2: of the three days a week I’m not doing a lifting class, at least two are dedicated to 30 minutes of another kind of movement. I’m a big fan of an outdoor run or an indoor spin class since I have my Soul bike at home.

I’ve realized that when I “fall off,” it’s rarely about how much I’m eating—it’s about what I’m eating. Translation: too many quick, easy carbs and sugar, not enough substance to actually keep me full. Meals that look great, taste great…and then leave me hungry an hour later.

So for this month, the shift is simple: Protein first. Everything else follows. Not in a hyper-optimized, tracking-every-gram/macro way, but in a “is this actually going to sustain me?” way.

What that looks like in practice:

• Building meals around a clear protein anchor (eggs, chicken, fish, Greek yogurt, etc.)

• Not skipping meals and calling it “balance”—I rarely intentionally skip a meal, but even last night, I rushed to go out and meet friends for drinks and didn’t have a proper dinner! No wonder I was feeling less than stellar this morning…

• Having 2–3 high-protein staples prepped and waiting in my fridge. This way, I’m not negotiating with myself at 8 pm over whether I should just ‘treat myself’ and Uber Eats cake for dinner. No noooo….instead, it’s about having marinated chicken ready for a quick salad, turkey meatballs cooked, or soft-boiled eggs on the ready—anything that makes the easy choice the right one. THIS IS SO KEY FOR ME!!!!

It’s less about restriction, more about structure and making sure I’m eating in a way that supports the workouts, the walking, and, frankly, my mood.

The goal isn’t to rely on motivation. The goal is to make the baseline feel like the most natural thing (habit stacking!!!!!), then tack on little extras where I can.

A few that make a real difference:

• I charge my phone in the kitchen at night and use my Hatch alarm clock to wake me up every weekday at 5:45a. No snoozing!

• Always doing my shake plate for 10 minutes when I come home from my morning workout

• 10-minute walk after meals

• Walking to and from work

• Throwing in a short apartment workout for low-energy days

• Keeping a few high-protein staples on hand so meals don’t require a full decision-making process

Nothing extreme—just small habits (and a little bit of prep) that make the right choice feel like the obvious one.

Spring training isn’t about your best days. It’s about the power of raising your collective average.

Instead of asking, “Did I do this perfectly?”
Ask: “Did I do enough to keep momentum?”

• A walk instead of a full sweat is still something

• A protein-forward meal earlier in the day can quietly course-correct everything that follows

• Every night doesn’t need to end with ice cream, but some do! The key is balance.

You don’t need to check every box—you just need to keep moving ahead.

If your Spring Training is about health, by the end, you’ll probably feel leaner. More energized. A bit more on your game.

But the real shift is subtler: That feeling of being back in rhythm. Of following through. Of moving through your days with just a little more clarity. If you want to dive in, start by:

• Choose 3-4 pillars and write them down in your notes app. Create a checklist and track it!

• Aim for consistency over perfection

No dramatic reset required—just a month of showing up for yourself in small, repeatable ways. By May, you’ll feel it!

But admittedly, mapping out the framework is the easy part. The follow-through is where it gets impactful. For my paid subscribers, I’m sharing the exact system I’m using this month—my daily checklist, the habits that quietly make everything else work, and the no-thinking-required meals keeping me on track.

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Oh, how I missed her. It’s been soul-reaffirming to be back in the swing of things and reigniting my routine since returning from Seoul.

Yesterday, after going to The Class, I did my usual walk from Tribeca back to West Village, popping by Rigor Hill Market, snagging provisions at Murray’s Cheese, and ultimately winding up at Abington Square Market. Fully leaning into the joy of it all, I found myself picking out my second round of weekend tulips in two days. I mean, the limit simply does not exist for how many tulips one needs in their apartment on the first spring Saturday of the year!!

It was then that I found myself meandering over to the last vendor at the market, intently reading the ingredients on a roasted garlic and caramelized shallot soup. Despite having my headphones in, I heard a muffled voice next to me remarking on how good the soup was. Upon popping my earbuds out and turning to my right, what a delight it was to realize that the voice was that of Andy Cohen. We ended up chatting for a moment on books (he recommended Long Island Compromise by Taffy Brodesser-Akner), and ultimately, his endorsement convinced me to get the soup.

God, I love New York.

• Some thoughts on “getting your bag” (literal and figurative)

• My code to get you a free month at Vivrelle—your key to luxury handbags on a membership basis

• The Vault (Paid Subscriber Exclusive): everything I bought in Japan and Korea

• The Vault (Paid Subscriber Exclusive): your Korean beauty checklist

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The idea behind this essay has been percolating for weeks. Sometime between doing an unplanned fulllllll send at Prada in Milan, scoring a 2008 Celine duffle bag at a vintage store in Soho, and leaving Tokyo with an early 2000s Fendi Baguette (pictured below on her first NY frolick), it felt like time to put pen to paper—or rather, keyboard to Substack—on some of my deeper thoughts behind the meaning I ascribe to handbag acquistion.

So, let’s talk “getting your bag” in the literal sense. Growing up in a rural town in Western New York, I didn’t have the language or real-life reference points to understand anything “designer.” To be clear, I had everything I needed and more, but there was no frivolity.

If you’d asked me in middle school if I was aware of what Chanel/Louis Vuitton/Hermès were, I’m genuinely not sure what my answer would have been? From watching The Rachel Zoe Project, perhaps I had an awareness that these brands existed, but certainly no tangible touchpoints to experiencing them IRL. [Oh, what bliss to have been so sheltered from the realities of consumerism…]

By the time I was seventeen, I’d gone to Paris and walked the Champs-Élysées. I’d seen the flagship Cartier/Dior/Goyard shops (from outside) and was vaguely aware of these legacy brands’ cultural relevance, but I had no thread pulling me towards coveting the goods they produced because it seemed so very far from what was possible. No, no…the desire to own a designer bag wouldn’t be deeply rooted in my consciousness for years to come.

Fast forward to post-college life—when my first job paid $30,000. I’ve written about this formative period (an era when it was not uncommon that I’d get my card declined at Trader Joe’s) before, but not necessarily in reference to how my world began to expand, and with that expansion, so too did my desires for material goods.

It was around this time that I began watching old seasons of Sex and the City, lusting to live in New York, and started being exposed to people who actually owned designer goods. My frame of reference was changing, and with that, I found myself coveting things that now felt tangible, despite being far from my reality—that is, one that revolved around living on my own for the first time, having a car payment, school loans, insurance, and no idea how to balance it all.

At the time, I would’ve bitterly told you that no one was handing me down a bag…how wildly unfair!!!! Thinking back, I can practically hear my inner monologue stomping its proverbial foot. Because I wasn’t just ~jealous~ in those moments when I’d compliment someone on their YSL/Ferragamo/Gucci/Bottega, only to be met with a breezy, “oh thanks, my mom didn’t want it anymore!” or, “thanks, I stole it from my sister’s closet!!!!”…I was incredulous.

Did they realize how lucky they were, I wondered?? These lived experiences—walking in parallel with mine—were unfathomable.

I knew that if I wanted any of those things, I’d have to be the one to buy them. No handbag fairy was coming my way!!!!! And I’m embarrassed to admit that I used to have a chip on my shoulder about that…as if it was my god-given right to be handed a purse that cost more than an entire semester’s tuition at my in-state school.

And so dear reader, that brings us to now—when I’m at a place in my financial journey where I’m just now able to start treating myself. It’s worth noting that despite having a very stable full-time career, I only feel empowered to finally “get my bag” because of my side income from this newsletter, from ShopMy, and from the handful of side projects I’ve begun doing (like my brand deal with Mastercard). So for all of you who’ve been a part of championing my growth in those arenas, THANK YOU.

But it’s this inflection point that brings on a whole different slew of emotions (less resentment, more guilt?), including a mix of gratitude, doubt, excitement, fear, and yes, continued lust. The thing is, I don’t want to end up like Carrie!!!! I don’t want to go and try an apartment and realize I could have, if only I didn’t blow it on bags/shoes/that mink coat I [almost] bought in February but resisted.

So it’s a constant state of push-pull. Of deciding what is worth it NOW and what I want to put aside for future me. Of choosing what I feel is worth investing in to create my forever wardrobe, and what is just a flash in the pan—this debate is the everyday struggle, and my new inner monologue. It’s no longer about whether I can have it—whatever shiny thing has caught my eye—but whether it’s worth spending my energy and resources on now, or better saved for something later.

I can’t think of a more poignant transition than this to talk about a brand disrupting the luxury space by affording you access to bags and jewelry via a monthly membership: enter Vivrelle. Their service allows you to try and test out goods from leading brands before fully committing! Because if it’s an investment piece you’re considering but not quite sold on yet, as part of your membership, you receive discounted prices to purchase items from Vivrelle's closet. But I’m getting ahead of myself!

Vivrelle is a membership club that lets you borrow designer accessories for a flat monthly fee—think rotating your closet in real time with pieces from Chanel, Bottega, and more, without the commitment of ownership. It’s the easiest way to tap into luxury on your own terms, swapping bags (or jewelry) whenever the mood—or outfit—calls for it. Use my code (KAYLADOUGLAS) for your first month free and consider it your gateway into a much more dynamic, infinitely more fun wardrobe.

use code KAYLADOUGLAS

Well, what could be more fitting for this shoppy edition of The Sunday Series than to break down all the things I bought in Japan and Korea? I know what a popular destination combo it’s becoming, so hopefully this edit helps you think about what to prioritize on your next trip.

• A pair of custom jeans from Maker’s Pride of Craft: I’M SO EXCITED FOR THESE!!! They are officially the most expensive pair of pants I’ve ever purchased but will be completely custom to meeeee and all made from Japanese denim. More to come when they ship in about two months.

• Two pairs of Onitsuka Tigers: including the quintessential Kill Bill yellow sneaker! I recommend the store in the main Tokyo train station.

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Window Seat

Seatmates: Kayla Douglas

This interview is part of Seatmates, a Window Seat series where tastemakers, travelers, and creatives share how they move through the world—what they pack, where they stay, and the travel rituals that shape their lives…

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2 years ago · 20 likes · 10 comments · Tori Simokov

Reflecting back on all the life that’s happened since, it’s remarkable just how much of my Substack has been written from this very vantage point—from Scandinavia to St. Lucia to South Australia and now Seoul, I continue to churn out this newsletter week after week, no matter where I am in the world. And with another trip to Australia (this time, Western Australia!!!) on the docket next month, I suppose it comes as no surprise that, as overwhelming as it can be to produce content on the road, I’m equally fueled by the opportunity to keep my “desk” view forever in motion.

Today, we traveled from Osaka to Seoul on Korean Air’s gorgeous A321neo—a delightfully spacious aircraft that made for a smooth ride on our ninety-minute hop to the K-beauty capital. If you’re interested in getting the scoop on what we’ve been up to while here, be sure you’re subscribed to where we’ll also recap how we traveled from New York on Japan Airlines’s stunningly outfitted A350.

Here on The Sunday Series, perhaps I’ll do a rundown of everything I bought in Japan and South Korea next Sunday…let’s just say, the fashion is FASHUN-ing here. Sick vintage bags (I’m still NOT over the gorgeous early 2000s embroidered Fendi baguette I scored in Tokyo). Plenty of tops from cool Japanese brands where notably, it’s all about layering. Sneakers made for long days of exploration—including the iconic yellow Onitsuka Tigers that felt very TSS-approved. Ceramics made with extra care in Kyoto. And naturally, snacks on snacks on snacks from 7-11. When I say we are acquiring some additional suitcases in South Korea for our K-beauty haul, I do not exaggerate.

But for now, back to the matter at hand. Today, I’m honored to be featuring , founder of , as our “Between the Lines” guest. Yes, that Sunday Scaries! The one with a million followers on Instagram that crafts the cheeky slams laptop till Monday* carousels you’re always sharing to your IG story.

While it would be easy to assume that @sunday.scaries is a faceless entity, one of my favorite things to do when dissecting the internet is to get to know the actual people behind widely followed accounts. After all, they’re the tastemakers driving so much of the cultural conversation. So, I couldn’t think of a more aligned guest to do just that with in my own newsletter, which is also aptly named after the all-powerful Sunday.

For context, in the six (!!) years of writing this weekly letter, I think Will is only the second man I’ve ever done an interview with—and our first straight male guest on TSS at that. But after chatting with my friend Xan, who kindly introduced me to Will, I was eager to share more about the behind-the-scenes building of Sunday Scaries with readers. I hope our chat helps keep your own Sunday Scaries at bay!

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Kayla Douglas: Will, you started back in 2013. What did the early days look like before you were sharing content with a million followers?

Will deFries: In 2013, I was living with my parents and operating it out of my bedroom. At that time, my life was living and breathing the concept of ‘Sunday Scaries’ — desperately single, struggling professionally to find my niche, going out two (or three) nights a weekend, and dreading my existence every Sunday night. Not that today’s content isn’t completely authentic, but that time of my life was the most representative of the ethos behind the brand.

And honestly, I do kind of miss it sometimes in a twisted way.

Kayla: A decade ago, did you know you were building a brand, or were you simply documenting a feeling?

Will: Somewhat, yes. I was also trying to create something that made people feel seen in their anxieties. Early on, it was somewhat established that the motto of the brand was something like, “We’re all less scared together than we are apart.” Driving that community through shared feelings and experiences is what really made me realize I could do it full-time. Even today, I try to operate with the same mindset.

Kayla: Can you point to a specific moment (a post, a reaction, or a piece of feedback) that made you realize Sunday Scaries had evolved from a clever phrase into something deeply embedded in our cultural lexicon?

Will: Though I didn’t come up with the term itself, I will take *some* credit for the rise of it. I think it would have been popularized regardless, but I was the first person to really do anything with it with an end goal.

Early on, I had several people I looked up to compliment my writing to the point where it was completely motivating me. Once I had that approval, it kind of became a “Why can’t I do this?” moment for me.

Once COVID hit, however, people really started paying more attention. My guess is because every day felt like Sunday for an extended period, but I was simply glad to be there for everyone.

Kayla: Tell us about your background in podcasting and how you approach this medium of storytelling.

Will: I saw a few other companies launching podcasts in 2016, and it just made so much sense to me as someone who values independent media. With no actual experience with the medium, I walked into an office on Monday morning and simply said, “We need to start a podcast.” From there, things just kind of fell into place.

When I started The Sunday Scaries Podcast in 2019, I really wanted it to be a more digestible way to take in my writing — that’s probably where the storytelling took off for me.

Kayla: For Instagram, so much of what you do comes down to sourcing imagery that hits on the zeitgeist. What does your curation process look like?

Will: I honestly just save photos I like and hope that they resonate with others, too. If I’m watching a show, I’ll end up defaulting to that world. If a celebrity is being hilarious or bougie lately, they’ll probably get included in a *slams laptop* post. There’s really not much thought behind it other than, “Yeah, this feels Scaries.”

Kayla: The internet moves fast (and anxiety faster). How do you keep Sunday Scaries feeling current without chasing every trend?

Will: I’ve always just had my own idea of what the brand is and can be, and I’ve let that guide me more than trends. Of course, I clearly pay attention to trends but I think I’ve become somewhat savvy in understanding what is timeless and what is temporary.

I’ve been interested in graphic design since 2002, when I illegally downloaded Photoshop, so it’s always been easy for me to see through my ideas. Or change them for the future, too.

Kayla: You were an early adopter of Substack, getting on the platform back in 2022. In what ways has your long-form content evolved on Substack since launch?

Will: When I first launched on Substack, I simply wanted to have that old-school blogging feeling that sparked Sunday Scaries in the first place. I had always envisioned the brand having a regular Sunday “guide” for people feeling lackluster, and Substack felt like the perfect way to deliver this.

Obviously, Sunday Confessions has totally changed the trajectory of the Substack. People really seem to enjoy them despite it being user-submitted content versus my writing. The older I get, the less I want to force my writing, so it’s been a nice way to keep things fresh.

Sunday Scaries

Your cure for the Sunday blues.

By Will deFries

These days, I’ve actually been posting simultaneously on my old website, sunday-scaries.com, which I’ve been enjoying. I’m such a visual person that being able to manipulate everything from a design perspective is almost essential for me. I see myself diving far more into that this year than I did last year.

Kayla: Escapism is inherently woven into your brand as you create content that celebrates the art of running from our Sunday Scaries. How does travel play a part in the future of what you’re building?

Will: The first case of Sunday Scaries I ever had was leaving a Mexico spring break trip in 7th grade. I remember sitting on the airplane and thinking, “Why do I have to leave?” Ever since, it’s been ingrained in me that the worst Sundays are the ones where you say farewell to your vacation.

Additionally, however, travel just feels so in line with everything I want the brand to represent — exploration, leisure, relaxation, and that escapism you mentioned. If there’s one thing that can cure a case of the Sundays, it’s a plush embroidered robe and a freshly made hotel bed.

Kayla: If you wanted to outrun your Sunday Scaries tomorrow, where in the world would you go and what would you get up to?

Will: My number one bucket list place to visit right now is Forestis in the Dolomites. We considered pairing it with our Lake Como trip in 2023 but simply didn’t have the time.

From what I can tell, it’s a true Sunday sanctuary that I’d love to capture on film.

EDITOR’S NOTE: FORESTIS IS INDEED WORTH BEING AT THE TOP OF YOUR HOTEL WISHLIST! I’VE STAYED TWICE AND IT REMAINS ONE OF MY FAVORITE PROPERTIES IN THE WORLD.

Kayla: If we were with you in Austin on a Sunday, where would you take us to spend the afternoon?

Will: A light drink at June’s has never treated me wrong on a Sunday afternoon. And hopefully, I’m splitting their shaved jambon sandwich with my wife before we go home and sink into some Love Island.

Thanks for reading, friends. Looking forward to being back stateside and in your inbox next Sunday. xxKD

I’m sending this Sunday’s edition from Tokyo—a destination that’s lived on my vision boards for so long that it’s surreal to be seeing it with my own eyes. For the full rundown on all things Japan, be sure to subscribe to Stay Awhile by where I’ll be breaking down everything about our time here with Four Seasons. In the meantime, we just shared some exciting updates on an initiative built around female-owned hotels that I think you’ll also love.

As far as today’s edition of The Sunday Series, I’m beyond thrilled to be collaborating with none other than , the discerning writer behind Corner Booth. Together, we’re using International Women’s Day to gush over the female-owned and led restaurants we both love across the city. Because each time you dine out is a chance to vote with your wallet—and when we can, we LOVE to put our money behind women, right?

I’ve been fangirling over Courtney’s Substack for quite some time, so this felt like the perfect moment to collaborate. If you’re on the hunt for someone who always knows the coolest bar, the coziest corner booth, and even the right book to bring along, she’s your girl. Brooklyn-based, Courtney’s New York restaurant recommendations are decidedly more geographically diverse than my West Village-centric recs—and for my fellow travel peeps, her curatorial lens extends even further. In particular, I know TSS subscribers would especially adore her little black book of 12 Paris mini itineraries. So without further ado, shall we dive in?

Corner Booth

Where to dine, drink and linger, told through stories and scenes from the corner booth.

By Courtney Presley

To honor International Women’s Day, Courtney and I did a fun little Q&A spotlighting some of our respective favorite female-owned and led restaurants in New York. I have a feeling you’re going to walk away from it with more than a few spots on your list!!!! We’d be thrilled to hear from you in the comments on where you’ll be prioritizing next—and if you’re feeling extra generous, a like or share on Substack to help this post reach more readers.

When you think about the women who shape New York’s dining scene, what spaces or people come to mind?

Courtney: My mind first goes to Rita Sodi and Jody Williams. With rigorously consistent, unwaveringly excellent restaurants like Via Carota and I Sodi, they’ve built institutions that define modern New York dining. Missy Robbins did something similar in Brooklyn with Lilia and Misi, bringing technical ambition to pasta but also instilling each with an energetic, slick swagger. I’m constantly amazed how chefs like Ayesha Nurdjaja at Shukette and Claire de Boer at King seem to deliver better and better meals every time I visit, raising the bar higher and higher.

And don’t even get me started on the meteoric rise and ongoing chokehold that Ha’s Snack Bar has on this city, thanks to co-owner Sadie Mae Burns. In the bakery world, Zoe Kanan at Elbow Bread and Kelly Mencin at Radio Bakery are reshaping how New Yorkers line up for carbs. I could keep going, but I’ll end with Annie Shi of Lei, who feels emblematic of where I like to think the city’s dining scene is headed: daring to invest in deeply personal projects, subverting expectations and continuing to expand the conversation.

Kayla: Echoing Courtney a bit here, but some of my favorite restaurants are under Rita Sodi and Jody Williams’ restaurant umbrella. I’ve been living in the West Village for over five years now, and Rita and Jody’s spots have fingerprints all over some of my most cherished memories! From the cozy brunch vibes at Commerce Inn, Paris-meets-New York charm of Buvette, lasagne with layers for days at I Sodi, aperitivo that makes you feel like you’re in Italy at Bar Pisellino, and of course, few moments are more iconic in downtown dining than a prime table at Via Carota, truly too many to count.

And when it comes to women influencing New York’s dining scene, I can’t not mention Ariel Arce. She’s behind so many of New York’s coolest spots, including owning Tokyo Record Bar and Pearl Box. Plus, she’s a part of the team that brought Roscioli from Rome to New York! As if that wasn’t enough, she has her own caviar company, Big Pearl Caviar.

Why does it matter who is behind the restaurant?

Kayla: Just like it matters what brands we shop, I do think it matters who is behind the restaurant. In an age where everything feels like it’s becoming more impersonal and an inundation of AI into all we do, hospitality is an industry that will always be powered by people. I’m a big proponent of becoming a regular somewhere, and the number one factor that influences me to want to come back to a restaurant time and time again is the people behind it. You can tell if you’re dining at the kind of place where someone wants to show up—where they have banter with their fellow servers and barbacks and the team in the kitchen. I want to support restaurants that feel like a place where people want to be.

Courtney: Kayla said it best! Behind any great thing, there’s a pair of hands that shaped it, a brilliant mind that dared to imagine it and a heart that injected it with soul. Restaurants are no exception, and learning more about the who, how and why behind them imbues dining experiences with so much more purpose and texture for me. There’s a story behind every corner booth, and I’m obsessed with uncovering it, supporting it and sharing it.

Tell us about a female chef or restaurateur you deeply admire.

Kayla: I’m low-key one of Caffè Panna’s biggest fans, so that admiration extends to its owner, Hallie Meyer. Sure, she’s the daughter of one of New York’s most legendary restaurateurs—so you could argue it’s in her blood to be in the hospitality business, but what she’s built feels distinct. I am forever in awe of the creative collaborations they churn out each week, as well as unique flavors at grocers like Murray’s Cheese and Meadow Lane. I just had a flavor last weekend (cherry oatmeal cookie with a cinnamon base!) that blew my mind.

Courtney: Ok now I have an intense craving for ice cream…

I’ve developed a slightly parasocial bordering on obsessive admiration for Patricia Howard, the co-founder of Dame, Lord’s and Crevette, after religiously following her since the pandemic-era fish and chips days. Along with her husband Ed Szymanski, they’ve now built an ambitious, sharply defined collection of restaurants, each with a distinct identity and carefully-crafted point of view. The palpable passion she pours into each project is magnetic, from sourcing vintage plates across Europe for Lord’s to figuring out creative solutions for the floor-to-ceiling black bathroom tiles that were once at Crevette. She also brings a sense of brutal honesty to the work, especially when it comes to sharing the realities of building a hospitality group while raising a newborn. She’s a force, both for what she builds and how she builds it.

Where do you go when you want to have a cathartic dinner with the women in your life?

Kayla: In the spirit of prioritizing female-owned, I’d like to plan my next girls dinner at King! I had the chance to go up to their sister restaurant, Stissing House, with my sister, mom, and aunts and was blown away. I love that the two are led and owned by chefs Jess Shadbolt and Clare de Boer, alongside GM/beverage director Annie Shi, with such a clear vision. King is so cozy, and the forever-changing menu is super seasonal—so, it goes straight to the top of the list for a little kiki.

Courtney: I spent about four hours at Stissing House the last time I was there to celebrate getting engaged with my sister, so I second that pick. In the city, I don’t even know how many hours I’ve spent locked in deep conversation with my closest girlfriends at the tiny wine bar Della’s, founded by Liz Nicholson, in Tribeca and Cherry on Top, founded by Cerise Zelenetz, in Bushwick. And yes, I know the question was about dinner, but the most cathartic moments often prioritize heavy amounts of wine.

What would your ideal three-part night celebrating women in the city look like?

Courtney: I have two itineraries up my sleeve that are on my mind to do this month with my sister or some girlfriends:

• A literary evening with seafood small plates in Cobble Hill: Head to one of the many upcoming book events I have my eye on at Books are Magic, featuring inspiring women in conversation, like Zahra Tangorrain with Helen Rosner or Holly Brickley with Coco Mellors. Afterward, I’d stroll down to Saint Julivert, a French wine bar from chef and co-owner Alex Raij, nestled right next to the peaceful Cobble Hill Park. End the night at one of my favorite women-owned bars in the area, such as Clover Club from Julie Reiner or TALEA from Tara Hankinson and LeAnn Darland.

• A cozy crafting-centric, pasta-fueled outing in Fort Greene: Peruse the workshops I’ve always been intrigued to try at ReCreate Collective, founded by Liz Chick, such as funky still life drawing or vintage beaded jewelry making. For dinner, savor Silvia Barban’s delectable pastas at LaRina Pastificio & Vino, before heading over to try a variety of wines at the Parisian-style bar from Cali Faulkner.

Kayla: Okay, the Books are Magic idea is soooo good! I love that New York always has a cultural activation we can sink our teeth into…one offering that’s been on my mind lately is frequenting the galleries in Chelsea more, particularly on Thursdays when many of them are buzzing. I’m looking forward to a warm spring night soon, when I meet up with friends at Nicola Vassell Gallery on W10th before moseying over to Shukette for dinner. I’m fortunate to work down the street, so it’s been a go-to for some time! I love nights when chef and owner Ayesha Nurdjaja is in the kitchen cranking out her signature Middle Eastern dishes. For a nightcap, we’d go to Bar Bonobo on the way back to the West Village; this female-owned bar on 8th has such fun cocktails, including a “CornStar Martini” that’s served with popcorn.

What’s one small way we can be more intentional about supporting women in hospitality?

Courtney: I’m going to cheat and say a few! Seek out and sip wines made by women—places like Aperitivo by Carta are even spotlighting women-owned and produced bottles this month, curated by wine director Rebecca Powelson. When you’re buying a hostess gift or dinner party essentials, skip Amazon and support women-led shops like Big Night from or Coming Soon from Helena Barquet and Fabiana Faria. Read the work of women writing about food and hospitality, like All Consuming by Ruby Tandoh, Care and Feeding by Laurie Woolever, Save Me the Plums by or Will This Make You Happy by Tanya Bush. Put in an order the next time there’s a Fillings drop or a Sour Cherries pop-up. And of course, show up and eat! This month is the perfect time to visit places on your list to try, like Bong from Chakriya Un, Sunn’s from Sunny Lee or Hellbender from Yara Herrera.

Kayla: Personally, I know I can do a lot better job of keeping a running list of female-owned restaurants that I can support. Courtney has given me so many ideas by way of this Q&A that I’ll for sure be taking note of!!!

What book would you bring to a solo dinner at a women-led restaurant right now to match the vibe?

Courtney: I’m itching to dig into the new short story collection Brawler, from one of my all-time favorite authors, Lauren Groff. Her lyrical writing packs the kind of profound, provocative punch that lingers with you long after the tale is over. The nine stories, described as reflections on “the ceaseless battle between humans’ dark and light angels,” deserve a setting that feels intimate and intentional, a place where you can take your time sipping some wine solo and letting each story settle in, somewhere like Plus du Vin in Williamsburg, co-owned by Carenn Mackinnon.

Kayla: Okay, I know the idea of solo dining puts most people into a tizzy, but I happen to love it—so long as I have my book in hand. I’d like to do a solo sesh at The Odeon bar, one of my favorite spots to walk-in in Tribeca. Female-owned since the 90s, it’s also an iconic watering hole. For this solo sesh, I’d bring along the copy of The Bell Jar by Sylvia Plath that has been sitting on my nightstand for six months, as I’ve prioritized newer titles.

If you could invite three women to dinner in New York, who would they be and where would you go?

Courtney: To bring the conversation back full circle from the first question, I’d want to bring together Rita Sodi, Ayesha Nurdjaja and Annie Shi for a rich conversation on the past, present and future state of dining in New York. I wouldn’t be upset if Rita offered up a corner table at Via Carota for it.

Kayla: Reese Witherspoon, and Dua Lipa…the three book club magnets.

If you missed my post pairing tables to titles, may I humbly suggest you start there? I loved building on this list with Courtney, who is also using Women’s History Month as a reason to reach for books by women authors that dissect deeply female experiences, from sister dynamics (a plotline that always gets me!!) to marriage struggles to workplace pressures. Below are a few titles at the top of our lists, each paired with a women-owned bar or restaurant that matches the mood.

Courtney: Blue Sisters + L’Apero by L’Appartement 4F

Ever since devouring Cleopatra and Frankenstein by Coco Mellors—an all-time fave of mine—Courtney has been eager to read her second novel, Blue Sisters, which tells the story of three estranged sisters as they navigate the unexpected death of their fourth sister (cheery!). We both agree that Coco’s witty, beautiful, character-driven prose would unfold best when enjoyed in a candlelit, intimate space over wine and cheese, like L’Apero by L’Appartement 4F, co-owned by the lovely Ashley Coiffard.

Kayla: The Sicilian Inheritance + Lilia

Lilia in Williamsburg is a temple of handmade pasta and golden-hour light—where every bowl and every guest is treated like a small act of care. Pairs well with The Sicilian Inheritance by because Lilia will keep you guessing, just like this fun, fast-paced book set in Sicily.

Courtney: Strangers: A Memoir of Marriage + Ci Siamo

With so much chatter and buzz around Belle Burden’s new memoir Strangers: A Memoir of Marriage, Courtney’s curiosity to pick it up has been sufficiently piqued. She knows this one may require a stiff martini and a rich bowl of pasta to pair with it, perhaps at the bar at Ci Siamo, from the always-impressive Chef Hilary Sterling.

Kayla: Broken Country + I Sodi

I Sodi in West Village is a jewel-box trattoria beloved for its lasagna and ritualistic simplicity—equal parts intimacy, precision, and tenderness. Pairs well with Broken Country by Clare Lesley Hall, a book that stuck with me for its powerful prose on the threads that bind us through decades, much like the delicately constructed I Sodi lasagne.

Courtney: Workhorse + Jupiter

You can always count Courtney in for a story on the wild world of New York’s prestigious fashion magazine scene. To tide her over until Devil Wears Prada 2, she’s been intrigued to read Caroline Palmer’s Workhorse, which follows an editorial assistant as she competes with wealthy colleagues to climb the ranks. A book like that deserves a glitzy setting in the heart of Manhattan’s media empires, such as Clare de Boer’s snazzy Italian eatery Jupiter, right in Rockefeller Center.

Kayla: The Guest + Pearl Box

Pearl Box in Soho is an upstairs cocktail lounge draped in 1970s-velvet glamour—red-carpeted stairs, mirrored walls, caviar, and a signature candy box that makes every martini feel like an event. Pairs well with The Guest by Emma Cline, intoxicating, elusive, and the kind of read that will give you the same hangover as Pearl Box.

Thank you so much to Courtney for joining me to create this piece. Wishing a very Happy Women’s History Month to all!! xxKD

This afternoon, I closed my bags ahead of tomorrow’s departure to Tokyo in record time. Typically, I’m known to be up late packing prior to leaving for a trip, but not this time—all thanks to styling guidance from my dear friend , the writer behind the column extra dressed (to which you should 10000% be subscribed if you’re not already). Caylee’s an absolute fashion genius, and it was beyond helpful in merging my packing method with her keen eye for mixing in unexpected pieces and accessories.

But before we get into the fashion fix of today’s letter, first things first! There are a fair number of new subscribers here. Welcome, friends!!!!!

I’m Kayla—and I’m so pleased you found your way here. As an expansion of what I do over on Instagram, here on The Sunday Series, I’m curating my vetted recommendations, interviews with people I admire, and a smattering of pop culture musings. Plus, paid subscribers are privy to lots of extra bits, incuding travel guides and more personal shares. For instance, in this Sunday’s letter, I’m delving into what I’m manifesting in March, plus a bit more on partnership I have been working on with Mastercard for many, many months that went live today.

• Your CBK-inspired spring uniform edit

• The Vault (Paid Subscriber Exclusive): what I’m manifesting in March

• The Vault (Paid Subscriber Exclusive): more about how I landed a partnership with Mastercard

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And as ever, this issue is too long for email (brevity has never been my strongest suit), so it’s best you read on Substack, where I’d be forever grateful if you engaged with this by ‘hearting’ it or sharing with a friend! xxKD

If your brain looks anything like mine at the moment, it’s all things CBK and John. The cultural phenomenon that is Love Story has taken over.

I had read Once Upon a Time: The Captivating Life of Carolyn Bessette-Kennedy by Elizabeth Beller (the book on which the series is based) last year before the show was announced with mixed feelings. While I enjoyed learning more about Carolyn’s background and her life before John, there were many, many creative liberties taken. And ultimately, it’s a sad story. Not just their young and all-too-tragic deaths, but when they were alive, the scrutiny under which Carolyn Bessette-Kennedy and John F. Kennedy Jr. were placed was inhumane.

And yet, it was this very real public obsession that inadvertently documented one of the most enduring style icons of the 1990s. Posthumously, CBK has become something of a Pinterest archetype. Her street style—understated, disciplined, impossibly composed—has been turned into countless mood boards and minimalist manifestos.

But what makes it resonate right now isn’t just nostalgia. It’s restraint, expressed through so many of her go-to looks: The silk slip under a severe wool coat. The sharp shoulder of a blazer worn with nothing but a tank. The almost stubborn refusal to accessorize, with the exception of her classic sunnies. Carolyn’s power wasn’t in novelty—it was in simplicity.

And we can’t talk about the CBK canon without mentioning how deeply influenced her wardrobe was by Japanese design. She gravitated toward designers like Yohji Yamamoto, whose work centers on drape, shadow, and architecture over embellishment. Notably, his designs were meant to make women feel like they had armour on…it’s no wonder Carolyn wore so many of his designs to galas on John’s arm. Her clothes were keeping her safe—sending a message about who she was (elegant). And perhaps, who she wasn’t (showy).

Which makes it feel almost poetic that I’m thinking about all of this while packing for Japan. Because Japanese street style—at its most compelling—isn’t performative. It’s constructed. There’s a discipline to it. A respect for silhouette. A fluency in layering without bulk. The kind of dressing that looks effortless only because it’s been edited with restraint in mind.

And when you start thinking about clothing that way, you buy differently.

You stop chasing trend pieces priced for a single season. You stop adding for the sake of adding. Instead, you invest in garments that hold their shape—literally and metaphorically. A blazer that doesn’t collapse when thrown in a suitcase and taken halfway aroudn the world. A pair of trousers that falls correctly over a flat. A coat that skims instead of swallows.

There’s a particular beauty in buying less and buying better. Personally, I’m aiming to build a wardrobe that feels cohesive rather than reactive. So instead of a spring haul, I’m continuing to build out my capsule wardrobe by adding in just a handful of pieces. Not in the beige/basics sense, but in a way that honors CBK-style restraint. So, here are some pieces on my radar if you’re craving a similar, thoughtful approach.

CBK-Inspired Capsule

• An impeccable navy blazer. This one from Veronica Beard has caught my eye. Alternatively, this fitted silhouette with a waist slip from Aligne is très chic. And, I don’t know if I’m cool enough to pull it off, but this oversized pinstripe blazer from The Frankie Shop is edgy in all the right ways.

• Tailored suiting. Specifically, I’m salivating over a set from Destree with this cropped jacket and these satin flared pants. Me wantttttttt.

• More tailored trousers. To match my favorite ever button-down (With Nothing Underneath’s Tencel Satin), I simply NEED these Rampling Trousers, also in 100% Tencil Lyocell Satin. Then, while splurgy, I’m completely gagged over these pleated Anther Tomorrow trousers in camel.

• A crisp white button-down. As previously mentioned, I adore the British brand With Nothing Underneath. Having amassed a solid collection of their button-downs (while styling me today, Caylee remarked on this because they are the most repeated brand in my closet), you can’t go wrong, but this one is great if you want something crisp. For something more approachable in price, the JW Anderson line for Uniqlo has some more relaxed-fitting, cropped shirts.

• Ribbed tanks for layering. If I’m being honest, the chicest ribbed tank I own came from a trip to Schostal in Rome, where, in hindsight, I should have stocked up. I found them online, but don’t hate me when you see the price…promise I paid a fraction in Italy. Very different, but I think I’m going to give these Buck Mason ones a try.

• Plain white tees. Was just having a chat about white tees with my friend Xan who has the most incredible closet. I’m severely lacking in this category but she’s a pro and stocks up on Victoria Beckham’s version. For something more approachable, Cos’ Clean Cut Tees are beloved. Otherwise, a more loose fit, there’s the two-pack of Rag & Bone Slub Tees.

• Tailoring denim. Admittedly, I really, really struggle with denim. My proportions are not very jeans-friendly, which truthfully turns me off from shopping for them altogether. Moving forward, I’m committing to getting past the fact that almost no jeans are going to fit me off the shelf! In fact, next week in Tokyo, I have a custom jeans appointment where they are meant to measure me and create a pair completely from scratch. I’m hyped.

• A smart flat that can survive 20,000+ step days. Let’s be honest, I covet a closet of Chanel flats, but that’s not on the cards at the moment. In the meantime, I’ve just stocked up on two pairs of velvet ones in Milan from a local shop; this dupe is close and well-priced. Alternatively, I’d love to add more Fabelus flats to my closet. I got a pair in Paris a year and a half ago that I’ve worn a ton and are still in great shape!

• Structured bags with architectural lines. I’ve been going a bit hard on the bags lately, so this is going to need to wait…but when the time is right, I’d love to add The Hudson from DeMellier in black lizard to my mix for work. For evening lewks, I still can’t get past swooning over a Savette Pochette bag which feels distinctly CBK-approved for its lack of branding.

Personally, it’s BIG manifestation energy for me having the past two months start on a Sunday. March feels especially momentus for a few reasons…one of which has to do which something a pyschic told me back in January about what would be happening for me this spring.

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Did you catch that nail-biter gold medal win for the US men’s hockey team today?? Full body chills. Between the men’s team snagging their first gold since 1980, the women’s hockey team also claiming an OT win against Canada, and Alysa Liu’s poetic performance, these last few days of the Games feel like they’re following a movie script.

Before we dive into all of our Milano fun, I need to take a beat to look back at last Sunday’s letter. If you haven’t had a chance to read it just yet, I’m shamelessly going to redirect your energy to what was a very special “Between the Lines” edition with . I’m still not over her thoughtful answers and what an honor it was to feature a creator whom I’ve admired for so long.

Go "Between the Lines" with Julia

Before we dive in, a quick note on what this recap is—and in equal measure, what this Mini Milan Guide isn’t.

I’ve written plenty of destination guides for my paid subscribers in my years of writing TSS (including Nantucket, Paris, Mallorca, and more), each meticulously crafted after multiple visits to a destination—once I’ve wandered enough neighborhoods, tested plenty of tables, and stayed in enough hotels to feel like I can offer holistic recommendations.

And while it wasn’t my first visit to Milan, I hadn’t been back since I was seventeen, so it may as well have been. With the Games as our primary focus, our time at leisure was limited. So, think of this as my curated edit of Milan, shaped by Olympic energy, tables recommended by trusted locals, all anchored by two very chic hotel stays. It’s not exhaustive, but a roundup of exactly what I feel is worth your time. As always, I’m reserving these tidbits gleaned from my visit for paid subscribers.

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On that note, let’s dive in. The city was absolutely abuzz with energy during our time on the ground—from brushing up with Martha Stewart at the original Prada store to spending a perfect 60-degree Sunday having lunch at a local friend’s favorite trattoria, we were riding a major high the entire trip.

For fear of being too name dropp-y, to further paint a picture of just how vibrant Milan felt this past week, beyond Ms. Stewart, Tieghan of Half Baked Harvest-fame struck up conversation with us while having coffee at Principe di Savoia, Regé-Jean Page (Bridgerton) was checking out of The Carlton as we were leaving the hotel for the day, and Seth Meyers was checking into our Emirates flight at the same time as us at Malpensa yesterday. Needless to say…VIBES WERE HIGH.

There are so many sensational hotels in Milan, even more so this year, with a great deal of development happening in the city. We did a split stay since we broke up our time with FORESTIS (more on this Dolomites oasis in a future letter) at two very different properties!

• Hotel Principe di Savoia: We were fortunate to start our trip in a well-appointed suite at the Principe. I’m a huge fan of the Dorchester Collection properties, and this stay was no different. Their team always nails it from a service perspective—they made us feel SO special, even going so far as to make our Valentine’s Day arrival extra sweet with red balloons anchored by photos of us! The club sandwich we got from room service on arrival revived me, and the sensational daily breakfast spread was also a treat to wake up to each morning. Notably, this hotel is turning 100 next year, so it’s got some old bones—you’re not coming here for the freshest product in town, but instead a property that has a soul.

• The Carlton, A Rocco Forte Hotel: On the complete opposite end of the spectrum, on our final two nights, we stayed at the newest property in Milan. Opened in November 2025, The Carlton is an elegant 71-room oasis. As with all other Rocco Forte properties, this family-owned gem was designed by Olga Polizzi and is bursting with color. The subterranean Irene Forte spa (her products are incredible!) and fitness center stood out as feeling especially fresh. Don’t miss ordering the carbonara omelet at breakfast. Especially love the location, with a back entrance directly onto Via della Spiga, a spectacular shopping street.

• Nuova Arena (Piazza Lega Lombarda, 5, 20154 Milano MI, Italy): This spot was the aforementioned Sunday lunch, and I can’t overstate how much we loved it. Probably my favorite meal of the trip, not just because we were the only table speaking English, but because the ambiance, service, and food were everything you want from a no-frills Milanese trattoria. Will be 10000% be back.

• Trattoria Milanese (Via Santa Marta, 11, 20123 Milano MI, Italy): Located in the narrow streets of the historic city center, this has been a meeting point for posh Milanese for decades. Here, we opted for prosciutto and melon, the classic veal Milanese, sauteed veggies, saffron risotto, and tiramisu. No notes.

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So it feels fitting that this morning unfolded as my ideal start to a Sunday: I woke up gently to my Hatch alarm, made an iced cortado in my Sunday Funday cup my friend got me, and burrowed back in Boll & Branch sheets to finish into the last 18% of Finding Grace by Loretta Rothschild. This book had me hooked from the beginning, but what I didn’t see coming was the full-body sobs evoked by the ending. Talk about catharsis.

Upon getting myself together, I immediately texted the group chat about how sensational the book was. And in that moment, I was srtuck with a reminder: this is why I read. To feel deeply. To metabolize the emotions I’m feeling in my own life through fictional characters who often look quite different to me, yet connect me to my own humanity. This realization feels like the right emotional footing from which to open today’s letter.

But before we get into that fun, last week’s edition of The Sunday Series was all about diving into February with a clear eye towards all the magic ahead. If you’re looking for a gift for someone you love, don’t miss my Valentine’s/Galentine’s Gift Guide.

Valentine's/Galentine's Gift Guide

Now, into today’s edition! They say not to meet your heroes. But lucky for me, I seem to have quite a few—and the handful I’ve crossed paths with have almost always met, if not exceeded, expectations. On Tuesday, I had the opportunity to interview one of my author heroes, Jessica Knoll, as the kick-off to our series we’re calling “Conversations on Creativity” in partnership with Murray’s Cheese. It felt fitting that the first installment of this in-person event series (be sure to subscribe to if you want to be the first to hear about our next one!) began with Jessica, whose work explores the inner lives of women with her signature sharpness.

What followed was less of a formal interview and more of an open conversation about burnout, boundaries, social media, motherhood, writing badly on purpose, and the small daily rituals that keep the creative spark alive. Plus, as a bonus, paid subscribers have access to our full forty-four-minute chat as an audio file right here within Substack, so you can listen, podcast-style!

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Kayla Douglas: What does your relationship to creativity look like? How has that evolved over the course of your career?

Jessica Knoll: I don’t know if I can, you know, if I can speak to it throughout my life, but I can speak to what my relationship is to creativity at this moment, which is surprisingly very good. I feel like I went through many years where I had many blocks, and I felt very frustrated. I felt very burdened. I don’t currently feel that way, and I owe that in big part, I think, to lightening my load.

I said “yes” to a lot of things for a couple of years that sounded really exciting, sounded like a sure thing, and I guess I had to learn the hard way that nothing’s a sure thing. No matter what A-list actress is attached to it, it’s not a go. But I still had to make my way through obligations that I had to people, and I finally delivered on some of those things over the last year, and I feel free in a way that has allowed my mind to really relax and come up with ideas that I’m really excited to kind of pursue and think through.

KD: And you mentioned actors being attached to scripts. I think everyone in the room knows that in addition to writing novels, you’re also a screenwriter. Can you give us a little bit of context—for those of us who don’t quite understand the difference—and what that means?

JK: When my first novel, Luckiest Girl Alive published in 2015, it was optioned by Lionsgate for film, and it was the time of Gone Girl, and Gillian Flynn was working with David Fincher, and she was going to write the script herself. And I just remember thinking, “If she can do it, I can do it,” you know? Like, I want to raise my hand. And so I pushed really hard to be the one to adapt it or at least take a go at it.

And it ended up becoming something that I loved. It really was a craft that I had to develop. So I did write the screenplay to that movie. Then from that, other opportunities appeared, which were not just adaptations of my own work, but adaptations of other books, adaptations of, like, viral Reddit stories.

I did one of those. It was, like, set up at Sony for a minute. [laughing] I’m just laughing, thinking about the actress who was initially attached to it because she’s currently a...I won’t say who, but she’s currently a very incendiary figure at the moment.

KD: Canceled, if you will?

JK: Yeah, canceled, if I will... but yeah, and then that, they were all like flops in the end. [laughing] Like, nothing went anywhere.

And so to have multiple projects on my docket that felt consuming to me, but I wasn’t able to give my all to them, that was a really crappy feeling, and it made me very depressed for a couple of years.

KD: That makes perfect sense. You sort of already answered this…I’m starting to realize a bit of your creative themes at this point. But I’m curious, as you become more traditionally successful, if you will, have you felt more pressure around your creativity, or how have you navigated that?

JK: I’ve recently had this revelation that what excites me the most is things that I don’t have to do. So, for instance, Luckiest Girl Alive, I started writing that novel in 2012 or 2013. In fiction, especially for a debut novelist, you have to have the whole manuscript written for an agent to take it out and hopefully get you a book deal.

So I sat down, and I started writing it, you know, and it was—they say in the entertainment industry, it’s called on spec, which is if you write a screenplay for no money, and then try and sell it. So basically, novel writing is like writing on spec for a debut novelist. So I wrote that book, and it poured out of me, and it was because I had, um, there were no expectations. There was no one breathing down my neck. There was no deadline. It was just something I did for myself.

And after that, I started to discover different kinds of avenues of writing that engaged that same state of flow, and I noticed that they were all centered around things that were not already set up somewhere. So I think in 2019, I had an idea for a horror film, and I sat down, and I wrote my first script on spec, and I ended up selling it to Amazon. It’s still set up at Amazon. Like, it’s still in development.

Who knows? We have a director attached, a great director, but we’ve had one attached for many years, so I don’t, I don’t know what will happen there. The new thing right now is people are selling short stories basically as treatments for film and television. If you have an idea, and you feel like doing it, you do it, but no one is expecting it from me, and I have, like, three ideas that I want to write.

But sadly, there are still some things that I have to do to keep a roof over my head,[chuckles] so I’ll never be able to escape that part of it completely. But I do like searching for those little, kind of creative nooks and loopholes in there.

KD: So when you’re thinking about the difference between how you set up a workday these days versus when you wrote Luckiest Girl Alive before your job, when you were at Cosmo at that time. It’s a very different scope to be finding a couple of hours of writing before your full-time job versus the pressure of waking up every day now and having to produce. So what does a good creative day feel like now?

JK: It’s actually not that dissimilar to what I did with Luckiest Girl Alive, where I still do my, my best writing in the morning. I used to be really precious about it, and it had to be that I woke up, and right away, I got to it. If I had to do anything else before that, it was like the day was ruined.

Like, I couldn’t produce. It was very tortured. Now, [laughs] I’ve loosened the reins on myself a little bit, and it still is, you know, the first work thing that I can get to. Like, obviously, you know, I’m a mom now. I have to take my daughter to school. I have to feed her breakfast. I have to convince her to let me brush her hair.

So I have, you know, like, an hour in the morning where I’m doing lots of things that are very time and energy-consuming, but I’m using a different part of my brain to kind of complete these tasks. So I still try to reserve my mornings for my creative endeavors. I think something I also learned over the years is that I’m very hard on myself, and so, when I wrote Luckiest Girl Alive, I only had a certain amount of time that I could work on it in the morning before my real full-time job.

After I sold that novel and, um, and I was able to just do this full time, I thought that: “Oh, okay, I’ll, I’ll write all day.” I mean, show me a writer who writes all day. Like, it just doesn’t happen. You just, you burn out after...I mean, some people have a better motor than others.

I felt like I was just procrastinating, and I had to learn that it’s okay to step away. It’s okay if you can only do this for a little bit. And more time doesn’t make me more productive—that’s the thing I eventually had to accept about my writing process.

KD: Besides writing for you, where else does creativity show up in your life?

JK: It shows up in really small ways. I think the walk home from my daughter’s school is when I just feel so excited about something I want to sit down and write or something I’m working on. It’s when I’m able to kind of unlock certain plot problems that I’m having. And it’s not a long walk. It’s like a twelve-minute walk, but I really cherish it. And showering.

Weirdly, it’s warm, and it’s relaxing, and I think I relax, and I just…I don’t know. My mind is at ease, and also at night, if I’m woken in the middle of the night, you know, my daughter wakes up or whatever, and I’m having trouble falling back asleep, I’ll try and, like, work through a plot hole, and it really soothes me, soothes me to sleep. So I find it in little moments throughout the day.

KD: Okay, so you’ve sort of touched on this, but I’m very curious, moving back to New York from LA, how that’s influenced your daily life, your approach to writing. I’ve been lucky enough to get my hands on a copy of Helpless, which we are also going to get to! But there is a line, and you reference the protagonist basically memorizing something somebody said to put it in their notes app. And I think as a writer, that’s such a real thing, where you’re like, “Wait, I’m watching this scene unfold in front of me in a restaurant. There’s so much happening in New York, you know, than where you go.” So how has that changed your approach?

JK: Yeah, I felt very isolated in LA. I felt like I got stuck in my house a lot. It was very hard for me to leave. I run kind of depressed anyway, and then you add, like, Lexapro to it. You’re, like, a little flat. [laughing] Yeah, it’s great, but, like, it doesn’t help me to get the motivation sometimes to get dressed. I had to deal with LA traffic, and I would have many days where I would not leave the house. And even when I became a mom, because she was still a baby, so it wasn’t like she had to go to school, I didn’t really have any reason to take her out of the house. And I always had bulldogs, and they’re super lazy, and they don’t walk. So that didn’t help me either.

The thing that I loved so much about moving back to the city this summer was how easy it was to leave the house. For someone who’s organized like me, it is the only way for me to get out into the world is the fact that I can just step right outside my door and everything is right there.

And you’re totally right. It’s the conversation. It’s like, I had a parents’ meeting this morning after I dropped my daughter off to school, and there was this—I’m working on this character right now, and there was just this dad who was sitting in front of me, and I’m like, “This is the character I was envisioning,”... exactly how he’s dressed. Like, he was so dapper, and he had a shaved head, and he kept running his hand over his bald head, and I was like, “What a great gesture,” you know? [laughing]

Dialogue, like, someone’s got to be doing something, you know? And I was writing it in my notes app. The parents behind me are like: “Why is she, like, texting right now?”

So yeah, New York just made me a part of the world again in a way that I think is good for my mental health as well as for my creativity.

KD: That makes so much sense. As we started to explore “Conversations on Ceativity” as an event series, you seemed like the most natural fit for someone we want to speak to in this space. I’m a huge fan of your IG stories on cooking. Tell us a little bit more about how being in the kitchen unlocks anything creatively.

JK: Well, I don’t want you to oversell me because I’ve all but stopped cooking since moving to New York. People, people will message me and say, like: “I miss your cooking videos.” And it’s kind of weird, I’ve never talked about this, but, I think I started really filming my cooking videos around the pandemic because, again, stuck in the house, there was nothing to do but to, but cook and drink and doomscroll, and that was the only thing giving me the will to live: coming up with new recipes and fun new cocktails to make.

But then it became this thing where I felt pressure to do it. Like, I knew people liked it, and people would always ask me about it. And I think when I got to New York, nothing compares to the takeout scene. I think it was also just so exciting to have new restaurants to order from. Like, you burn out on everything after a while, you know? So I think the novelty—I moved to LA in 2016, so all my New York restaurant preferences were also squarely stuck in 2016. So I was ordering Meatball Shop and Bareburger.

And I couldn’t get enough of these places that were those were the places that I was obsessed with when I left. So then I burned through those pretty quickly, and they kinda lost their luster, as everything does. But I’m still...I don’t know. I’m still really in my takeout moment. The kitchen that I’m in right now is not that great, and we’re looking to find a more permanent spot. So hopefully, if I have a kitchen that feels more inspiring to me, then I’ll do better work then.

KD: Well, you touched on something that I’m actually kind of curious about delving into, and that’s the performance of social media. As an author, knowing that it’s a vehicle for you to promote your work, but also, be a person in the world. How do you think about—let’s use Instagram specifically—that channel, and how do you navigate the boundaries that you’ve decided feel good for you there?

JK: Instagram has always felt very easy and natural to me in a way that Twitter never did. Now, X. But, I got rid of it when it was still Twitter because I was like: I’m just, like, I’m embarrassing myself on this. I was trying to be, like, quippy, and it just wasn’t hitting.

Whereas Twitter felt very numbers-driven, so does, obviously, the main grid on Instagram. I attempted TikTok, and I’m like, I love it as a lurker, but, I’m too old. I don’t have the natural touch, you know? I’m firmly an elder millennial who just gets Instagram stories.

And it works for me, and so, like, I’m gonna stick with what’s working for me. I think because of that, I have natural boundaries around it. Sometimes I get self-conscious that I don’t have much going on beyond being a mom. And I’m like: Oh, is that boring? Before I was a mom, I thought kids were so boring. But now I think they’re all precious and cute. [laughing]

I got a dog. I didn’t think all dogs were cute until I got a dog, and I was like, “Every dog is beautiful.” [laughing] I feel about children now. Like, I can’t believe I was such a Grinch before. And I love seeing people’s kid posts, so I’m like, I don’t know. Hopefully, most people out there are, like, aren’t as bitchy as me, and they think my kids are cute. But then it also becomes a weird thing because I’m like, she’s growing up, and then, like, am I violating her privacy? I’m gonna model myself after Andy Cohen’s approach, which is once they get to be, like, three or four, he keeps them off camera. I mean, but don’t, don’t pin me down on that.

KD: Well, this is a great transition to talk about your upcoming novel, Helpless, out in July. We’d love to know more about why this story felt relevant for this moment in your career, and what called you to this story?

JK: Yeah. So this book is a departure for me in that it is, um, very sexually graphic. Which is an awkward conversation to have, keep having with my mother-in-law, which is like, “Don’t you have an advanced copy?” And I’m like: “Barbara, I can’t send you a copy of this book. Please, I hope to have a long career, and maybe the next one will be for you.” [laughing]

I don’t think I’m far enough out of it yet to really understand why I felt I had to write this book. But I will say, I went through looking all around, and it’s like, okay, Colleen Hoover is off the charts, like all the Romantasy series. Like, I got in deep with A Court of Thorns and Roses. There was, like, six months of my life that I disassociated with those novels. Like, I only thought about Nesta and Cassian, and I was like, what has come over me? And I became obsessed with finding erotic things to read that also felt dangerous. And I just felt like there was limited inventory with writing that also felt good to my eyes. You know what I mean? So I read Susanna Moore’s In the Cut, which, oh my God, talk about a great New York City erotic thriller. Like, oh, my gosh, it’s super, super nasty.

It’s so good. And, I mean, Susanna Moore's writing is unbelievable. Ali Hazelwood is also a very intelligent writer, and I liked her paranormal series because I like darkness. So I find that normally her stuff is so well written, it’s still not, still not bloody enough for me. [laughing]

And I was like, I’m literally going to create a f*cked up fantasy that’s, like, in my head. And I don’t know, I just always assume everyone is as f*cked up and demented as I am,[laughing], and some people are reading this, and they’re like, “Whoa, Jess,” like I don’t know. So I’m giving everyone a fair warning. But, I did have something to say, right? About what pop culture trends and the way that they kind of uphold certain standards around women’s subjugation, and why it is that we ourselves even seek it out and sometimes even fantasize about it.

And I think that we’re seeing that everywhere. We’re seeing that with trad wives on TikTok. We’re seeing that with a BDSM version of Wuthering Heights, you know, and it’s like: Why do women fantasize about this, right? And that’s what the novel strives to answer. So you said you’ve only just started it, so I hope by the end you’ll feel that I’ve delivered my own kind of commentary on that, because that is what I set out to do. But yes, this one kind of explores that boundary between what is consent? What is abuse? What is power? And what is powerlessness? And I had a really good time writing this one. And I’ll move on, and I’ll do something else next time, but I really had to get this one out of my system.

KD: One of the things that immediately jumped off the page to me is just, you’re so good at voice, and I feel like your novels, for lack of a better word, are just so voicey. And that was something that really stood out to me as coming back into one of your stories, like, ‘oh, this feels familiar.’ And does that just come naturally to you? I don’t like to use the vernacular, ‘unlikable narrator,’ but it feels like you write these women who are complicated and complex, and in ways you don’t want to villainize them. So how do you think about that?

I’m like, there’s someone out there who, you know, is as kind of brutal as I am towards myself, towards others. I just think women probably have—most women just have such a harsh inner dialogue with themselves. At least, I do. And so I think that it comes easily for me to write like that, to write that voice in, in your head that you don’t feel safe enough using with other people. I find it to be very comforting to write these characters and to put them out there into the world, and to hear from people that they can relate to them. It makes me feel more connected.

KD: And I feel like anyone in the room who’s read Stephen King’s On Writing, his advice that you’re supposed to write at least the first draft, like, no one’s ever going to read it. Intimating certain people that you’re pulling reference points from. How do you think about that when you write a first draft versus when you’re editing?

JK: Writing with the door closed in terms of maybe the values of the character or the ethics of the story, that always feels easy to me. I can do that, and then I’m always surprised if there’s backlash, I’m like, “That is not, uh, not what I thought people would have issue with.” Where I struggle with writing with the door closed—which is an important part of the writing process—is writing badly.

It’s very hard for me to write a couple of pages that are just, like, shit writing just to kind of figure out the character and figure out the plot. I spend so much time trying to craft the sentence, and so my takeaway from that advice—writing with the door closed—is it’s okay. I mean, there’s this terminology people use, “the shitty first draft.” It’s okay for it to be a shitty first draft; no one’s going to read it. That’s my kind of hump that I’m always trying to get over. But the darker thoughts or characterizations, those all feel pretty easy. I don’t know what that says about me.

KD: No, I love it. Well, you mentioned shitty first drafts. Are you a plotter or a pantser?

JK: I’m definitely more flying by the seat of my pants. Although, I used to say that, but the more I do this and the more experience I get, I’m better at plotting, but not in a way that’s like I’m ever gonna make an outline, right? It’s like I can hold certain kinds of coordinates in my head and write from A to B, B to C, C to D. Whereas I think when I was first starting out, I only knew, like, I know what A is, and I know what Z is, but I don’t know what anything else is in the middle.

KD: So you knew the ending for your original, like your previous novels, you were writing to a particular ending?

JK: Yeah. Mmhmm. But now, Ican see a midpoint. I can see the arc a lot more clearly now. And I think that that’s just like a matter of experience, and it’s taken ten years, so, and I didn’t think it would ever happen, so I’m like, “I’ll take it.” But yeah, it comes a little easier now.

KD: I love that. So, in terms of people that are picking up Helpless, we talked about the voiciness of your novel always kind of being at the forefront, but what, for your readers of previous novels, do you think they’ll be like, “Ah, yes, this is a Jessica Knoll novel?” We talked about what’s different, but what’s the same?

JK: I think this one is a spiritual successor to Luckiest Girl Alive. My agent keeps saying that, and I think she’s right. There is something familiar, I think, between Faye, who’s my main character, and Ani, who’s my, my first main character. I think if anything, my last book, Bright Young Women, was probably the one that feels the most like, which one doesn’t belong, you know?

KD: Yeah.

JK: But in a way that I loved, and I want to return to again. But that one’s a little bit of a crowd pleaser. It’s one that my mom is so proud of. She had her book club read it, and I signed all their books, and I’m like, “You’re not gonna wanna do a book club with this one. But the next one, I promise, I promise I will write a book that you and Renee can feel good about…”

KD: For people in the room who aren’t as familiar with that novel, why did that approach...a Ted Bundy-inspired-story. Tell us about that.

JK: It’s my only novel that’s not set in contemporary times. So it’s a fictional imagining of the lives of the women who were affected by the serial killer Ted Bundy. And in the novel, I don’t name him. I only refer to him as the defendant. And there was a lot of research involved in this one. It’s the one that’s kind of closest to historical fiction. I spoke to some of the survivors. I read all the court transcripts, and I was a little nervous, like, can I realistically set a book in the nineteen seventies told from the perspective of young women in college? Am I going to get the lingo right? Is it gonna sound stilted?

And I’m really glad I pushed myself, and I’m really proud of that novel, and I’m actually working on an adaptation of that for a TV series right now. And the executive said, “You know, as much as you can to bring in the language of the seventies,” and I felt that same kind of nervousness again because I’m like, “I don’t want this to be hokey,” you know? Like, this isn’t my natural habitat. But it’s been really—I mean, I don’t want to say ‘fun’ because it’s obviously a very serious crime, and the survivors are very traumatized by it still to this day. But there is something about returning to the archives, I think, that feels like you get to create this world, and you get to live in it, and you get to really be enveloped by it. And that was my favorite part about writing that novel.

I loved going back into that world. I loved imagining the house that the girls lived in. I loved imagining their friendships and their strength. Not just imagining it. It was all there in the research. They were really extraordinary—what they went through and how they held their heads high throughout all of it. So I’ve been enjoying returning to, to those girls and to those characters.

KD: Our last question before we turn to audience Q&A, knowing how different your previous novel was from this one, how did Helpless challenge you differently from a creative perspective than your previous work?

JK: Well, it’s ultimately, I mean, it’s a f*cked up one, but it’s a romance in the end [chuckles] That has its own rules…I mean, it’s a dark romance, and there’s thriller components, and there’s murders, and there’s a mystery that’s unfolding. But I didn’t realize I was writing a romance until I got to the end of it, and that kind of has its own set of rules. I like to play in genre, so I don’t necessarily feel bound to, like, rules of a certain genre. But I did find that kind of coloring within the lines on this one, in my own way, to be very challenging.

But I think that I’m so proud and happy with how I figured it out and how I feel like I did it in my own way, in a way that also honors the genre. So I don’t know. I mean, people will have to read it and tell me if they feel the same, but I feel good about it.

Thank you for reading/listening! I loved this conversation so much. Jessica’s forthcoming novel, Helpless, hits shelves on July 7th. WVBC set up a special signed pre-order link (!!) if you want to secure your copy now.

Pre-Order a Signed Copy

Catch you next Sunday from Milano, where I’ll be spectating the Olympics!!!!! And don’t worry, upon return, as ever, I’ll share where we stayed, dined, drank, and shopped. In the meantime, as Euro fever sets in, don’t forget we have: The Paris Guide, The Mallorca Guide, The Balearics Guide, and so much more in the archives.

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Not only am I swoooooonig over a Sunday falling on the first of the month, but today also marks a Full Moon. According to my boyfriend (Chat GPT), the next time this happens will be Sunday, March 1st, 2037. That felt clinically insane to type…so you better believe I’m using this rare universal runway as an opportunity to go full ~WOO WOO~ on you.

• A simple full moon ritual 🌝

• Galentine’s and Valentine’s Edit: gifts for YOU, gifts for your girls, and gifts for him…if you must.

• The Vault (Paid Subscriber Exclusive): What I’m looking forward to in February

• The Vault (Paid Subscriber Exclusive): What I’ve been watching, reading, and listening to these days!

The thing is, whether or not you know it, I’m a part-time witch. I grew up in a house ruled by female energy (my poor dad!), am extremely close to my mom, sisters, and aunts. Essentially, we act as a little coven!!! When there’s a full moon, we’re often in close touch with updates on our manifesting routines. My Aunt Carol is especially in tune with the moon cycles and does fun card pulling rituals—here’s a link to a deck if you’re interested in having your own cards to tap into the Moon’s ancient feminine wisdom. Also, catch me doing The Class to fully activate my full witchy powers.

For me, it’s not uncommon on a Full Moon night to wind up on my building’s roof (if you are my landlord and reading…this is a JOKE, of course, I would never pass through the door that falsely claims an alarm will go off if opened and hang out on our unsanctioned roof) and do a little moon ritual. It goes a little something like this…

If you like marking moments—new months, seasonal shifts, quiet turning points—this is a simple ritual I come back to. Nothing mystical required, just a little intention and pause. The night of the full moon, I fill a glass with water and place it on my roof for direct exposure to the moon. If that’s not possible for you (perhaps you adhere to the rules of your building?), you can opt for a windowsill, counter, or bedside table. The point isn’t perfection; it’s presence. The water is meant to absorb the moon’s energy overnight—a symbolic way of marking the shift and carrying that intention forward.

Then, before leaving the glass, I take a few minutes to write out what I’m ready to release—habits, patterns, expectations, thought loops. Full moons are traditionally about letting go, and I like using this as an excuse to name what’s no longer serving me. I’ll either burn that list (safely, of course) or tear it up as a symbolic release. Then, on a fresh piece of paper, I write what I want to INVITE IN over the coming weeks and place that underneath the glass of water overnight, letting it sit beneath the moonlight.

The next morning, I drink the moon water and revisit the intentions I placed under the glass the night before. I’ll usually spend a few minutes journaling—nothing long or lyrical—just answering a few simple prompts to give the weeks ahead some shape. If you want a place to start, here are some prompts to consider for your journaling practice:

• What am I ready to leave behind?

• What do I want more of this month?

• What would make February feel meaningful—even in a small way?

The ritual works because it asks you to pause, reflect, and decide…an act we rarely do when on autopilot in our day-to-day lives. If nothing else, it’s a gentle way to mark a moment and remind yourself that you’re allowed to edit, release, and begin again—both incrementally and intentionally.

Aside from manifestation magic, February is also the month of love—in all its forms. As a single person, I’m choosing to embrace this not just in the romantic sense, but in the form of self-love and appreciation for the friendships that fill my soul. All of which feels like a long-winded way of saying: let’s lean into our gifting era. I’ve crafted an edit of things that feel useful, beautiful, and sometimes, indulgent.

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• Lip stain-filled locket that’s as gorgeous as it is functional.

• Happy ending mushroom chocolates formulated for arousal and pleasure.

• Rose colored matcha set for perfect at-home lattes.

• Silky lace cami short set that will make you feel like an elegant French woman.

• Massage candle in a chic curved vessel that makes for easy pouring (scandal!).

• Velvet decorative jewelry box with a two-toned pink and red tassel.

• Full body red light mat to supercharge your recovery, boost energy, and elevate your mood.

• Volume and style round brush in cherry red.

• Cashmere bandana created in Paris and knitted in Inner Mongolia.

• Italian-made slip-on velvet slippers perfect for lounging.

• Heart-opening bath soak with an Ayurvedic blend of calming rose petals and natural sea salt.

• Diva down embroidered heart ruffle throw pillow for the drama queen in your life.

• Heart-filled glass tumblers to upgrade any beveraginoooo.

• Scottish-made heart-embroidered sleeping socks that are 100% cashmere.

• Love-themed accessory that instantly pulls an outfit together.

• The tried and true setting spray that should be in every travel bag.

• A copy of Dolly Alderton’s book, Everything I Know About Love—a reminder that our female friendships are foundational.

• Card heart embroidered cocktail napkins to protect your table during your next girls night.

I’m not interested in overthinking gifts for men. I am interested in buying something thoughtful, elevated, and useful—ideally something he wouldn’t buy for himself, but will absolutely use.

• Lined leather gloves to keep him warm outside and shearling-lined mule slippers for inside.

• A new dopp kit in grained leather or, for the boujee man in your life, an upgraded set of two.

• Travel-size Theragun for the active, self-care king.

• An anti-aging bundle for the one who’s secure in his masculinity but also is afraid of getting older.

• A woodsy fragrance for your Tom Ford man.

• One indulgent wildcard: a limited edition Dolce&Gabbana x Bialetti Oro 3-Cup Moka Machine.

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For paid subscribers, I’m kicking off February by sharing what I’m looking forward to, in addition to rounding up what I’ve been consuming lately—books, shows, and articles that caught my eye. Consider it a collection of the things sparking joy, reserved for my most cherished TSS supporters.

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What makes this February Full Moon extra special is that we’re at the halfway point between the Winter Solstice and Spring Equinox. Meaning, from here on out, days only get longer. While the shift is subtle, there’s light at the end of the tunnel. Personally, I’m looking forward to so many things this month, including but not limited to:

• Our inaugural collaboration with Murrays: our Tuesday event where I’ll lead a conversation on creativity with author Jessica Knoll is sold out (!!!!!), but stay tuned as we plan to do them throughout the year.

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Writing to you from the most insane six-bedroom villa at Four Seasons Resort Los Cabos at Costa Palmas with my colleagues, straight off an absolute whirlwind of a work week. If you’re a reader of here on Substack, you know we just finished up our annual CORE summit in Santa Monica with back-to-back days learning amongst some of the finest in the hospitality. More to come over on our channels about the gathering soon! Be sure to subscribe to to get the skinny sent straight to your inbox.

To be honest, amidst this hectic ten-day work trip, I wasn’t exactly sure I had anything left in the tank to show up here today. But I’ve been so encouraged by the growth of our The Sunday Series over this past month, and it felt like sacrilege not to pop into your inbox…albeit with a highly condensed send from our usual TSS cadence. That said, there’s sooooo much content in my back catalogue—particularly for those with their eyes on summer trips that may benefit from consulting with one of my guides.

As a reminder, paid subscribers have access to my entire library of 100+ (!!!) issues of The Sunday Series, including Your Local’s Guide to West Village, A No-Gatekeeping Guide to Mallorca, A Mini Formentera Guide, Your Ultimate Paris Guide, Your Guide to Bozeman, Your Guide to Nantucket, My Holy Grail Rules for an Overnight Flight, 31 Ideas for Your Next Birthday Trip, A Playbook for How to Make Friends As An Adult, 16 Prompts for a Personal Quarterly Review, My 25 Favorite Books of 2025, 155 Hotels So Special They Are the Destination, and The Packing Method that Changed My Life.

Now, straight into what I’m in your inbox to share! I’m over the moon to be partnering with Murray’s Cheese on this first event in our “Conversations on Creativity,” a quarterly community event where we’ll bring in an author to chat about their work with our crew. That said, this first one, of course, needs to go well in order for us to keep them going!!!! It would mean the world to me to have you join us. Grab a ticket and invite a friend to come along. There will be wine, cheese, and lots of fun conversation.

GET YOUR TICKET HERE

And because we truly are aiming to support the author community with our in-person events and content creation, I’m thrilled to share that we’ve also partnered with McNally Jackson to do a special signed pre-order of Jessica Knoll’s forthcoming novel, Helpless. So even if you can’t make it to the event next Tuesday, you can secure a signed copy of her July 7th release—an option currently exclusively available to our WVBC community.

PRE-ORDER HERE

Signing off with this bookish send by sharing both my top reads of the year above, as well as our entire book club’s fave books of the year here.

Considering I’m currently on my laptop in the middle of our kitchen while our crew sips on nightcaps (which is wildly inappropriate!!!!) I’m going to sign off thanking you for the grace in making today’s edition short and sweet. I’ll check back from New York next week with lots of fun updates! In the meantime, please let me know in the comments if I can expect to see you at Murray’s—can’t wait. xxKD

After over four hours on the runway at Newark and another forty-five minutes trying to connect to in-flight wifi, I’m writing to you upon the devastating realization that my in-seat power outlet doesn’t work. This, of course, comes after bringing my devices to their ~last legs~ following hours of scrolling and streaming (TG for Landman season two!!!!) whilst in the de-icing queue. Combine my immediate panic with the guilt that I didn’t just crack open a book the entire time?? Yeah, needless to say, we’re getting off to a ROCKY start on this ten-day trip to LA and Cabo.

The thing is, travel isn’t always glamorous. A lot of the time, it’s weather delays. Your upgrade not clearing. The gate agent making you check your carry-on. Old aircraft with broken seats. Sometimes—especially if all of the aforementioned have coalesced in one single journey—realizing you (foolishly) didn’t replenish the snack bag on the day you really need them most can be enough to drive you to the brink of tears. And even then? I still love it.

If you’ve been a reader of The Sunday Series for a while, you likely know that I’ve been working in the travel industry for over a decade. In that time, I’ve gravitated towards the kind of writing that captures the more nuanced parts of both the getting there and the destination itself. So, today’s letter is especially meaningful to me as we’re returning to my “Between the Lines” series with a Q&A featuring writer whose work lives squarely in that liminal space bridging aspirational and authentic.

And to keep the travel theme going, I’m delving into an adjacent topic, too. Paid subscribers will be privy to a recap of how I’m maximizing my credit card strategy this year to optimize travel perks. Hint, hint for those who are also on Bilt 2.0 TikTok: it involves shifting to Ms. Sapphire Reserve. But, more on that later!

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Monica Mendal is a writer, editor and brand consultant focusing on fashion, travel and lifestyle. She contributes regularly to Vogue, T New York Times Style, Architectural Digest, and more. Previously, Monica was a fashion editor at Condé Nast Publications, such as Vogue, GQ and Glamour.

Kayla Douglas: You launched your Substack, So there’s this place... a little over a year ago. What’s the ethos behind it, and what do you hope readers feel when they discover your work there?

: I’ve been an editor for nearly 15 years, including almost a decade as a travel editor. To be a good editor, I believe having a point of view is essential. It’s not about endlessly rounding up the “best” hotels or spotlighting the same hot spots in familiar destinations. For me, it’s about tapping into the soul of a place, bringing a distinct perspective, and offering something thoughtful or nuanced in an increasingly saturated content landscape.

If you’ve followed me for a while, you know I’m drawn to less-traveled places and thoughtful alternatives to the obvious choices. The world is huge! There’s so much to explore and so many fun ways to explore it. Much of my work appears in magazines (both online and in print) but with my Substack I wanted to give my readers a more intimate look at my travels. For the wholeeeee story, I defer you to my first Substack post :)

So there's this place...

So there's this place...

Hi! Welcome to my little corner of the internet! It’s not lost on me that you’re likely here for one of two reasons: 1. You follow my travels on Instagram (have also maybe/hopefully read some of my published work!?) and are constantly wondering WTF I do and how I got here, or 2. You’re a friend or family member who I’ve guilted into becoming a paid subs…

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a year ago · 127 likes · Monica Mendal

You made the decision to relocate to Paris—what drew you there, and how has it shaped the stories you’re now drawn to telling?

I spent much of my adult life living and working in NYC across different publications at Condé Nast. When I went freelance and decided to transition into travel writing, I asked myself the tough question: why was I spending a premium on rent in NYC when I was traveling 3/4 of the year!? After a summer living in Milan, I knew I wanted to move to Europe for good.

So as soon as I got home, I gave up my apartment and started the process. While I did try to move to Milan initially, the Italian visa is much harder to obtain than the French visa, so I pivoted and landed in Paris. I studied here for a semester in university and Paris has always felt like home, so it was a relatively smooth transition! Really, what’s not to love about Paris? The move has allowed me to travel more easily around Europe, so I get to visit more places throughout the year. It still blows my mind that in 3 hours and 15 minutes I can be in Athens! I’ll never take that for granted.

What does a “good writing day” look like for you right now?

Oh, my answer is so boring. I’m sorry! But I am not one of those travel writers that can write on a train, plane or hotel lobby. My life would be so much easier if I could! Unfortunately, I rely on my routine to get writing done. I like to enjoy my trips and be fully present while traveling, then when I get back to Paris, I’ll hit my co-working space like it’s a corporate office and work straight from 9-5!

What feels creatively generative for you in this season of life?

Travel! That’s why I’ve made a living out of it :)

How do you approach sharing your work and travels on Instagram versus in long-form content?

I don’t really think about it too much. I’m not an expert on social media by any means. I’m a millennial! Social media was only just beginning when I started working. I sort of just share what I want to! I do think Instagram has been an incredible resource for me professionally though as it’s allowed me to connect with so many interesting people around the world!

What book on your TBR pile are you most excited to pick up next?

Slanting Towards the Sea by Lidija Hilje.

The Sunday Series was conceptualized as a love letter to my favorite day of the week. If we were with you in Paris on a Sunday, where would you take us to spend the afternoon?

In hopes that it’s an unusually sunny Sunday in Paris, I love walking along the Seine where the bouquinistes set up shop. It offers one of the best vantage points for exploring the city. You can see it all while getting a solid 30k steps in ;)

It’s been just over a year since I last weighed in on my credit card strategy, so between the launch of Bilt 2.0 card this week and my desire to do a proper audit heading into 2026, it felt like we were overdue. Selfishly, this check-in is as much for me as it is for you! In this breakdown, I'm reviewing which cards are truly worth their annual fee for how I travel, where I’m shifting spend, and how I think about maximizing benefits without overcomplicating things.

It alllllll started when, after flying over 20,000 miles with United in December, I found myself poking around their newly redesigned app a bit more than usual. It was then—during the final week of this year—that I realized I was about $1,500 short of hitting the $10k spend threshold on my United card to get a $100 credit towards a future UA flight.

Granted, $100 doesn’t even cover half a flight to Buffalo (where I’m from—and NO I don’t want to talk about the game last night!!!!), but if you’re immersed in the world of points and miles, you know these benefits add up, especially when an annual fee to have the card is at play. Missing out on a perk when I was that close to qualifying would’ve been silly!! And so, that’s the story of how I found myself in Soho on December 31st, within an hour of the store closing, purchasing the checked suitcase I’d been meaning to buy anyway.

The thing is, I was always going to get it—but had I not been paying attention, I likely would have made the purchase in January on my (then) primary card, my Delta Amex. Instead, the last-minute kerfuffle felt like a call to action: 2026 is going to be about paying attention and maximizing more mindfully. Because the goal is to be channeling a whole lot more of what is pictured below—and that spirit becomes easier to embody when we’re optimizing our travel spend…

Before we get into the card mix…some important context!!

A few things worth noting before anyone runs off to open five new lines of credit…

• I’m OBVIOUSLY not a financial advisor. Though I have worked with one for over seven years (if you want a referral to someone incredible, let me know!). This breakdown is simply a result of years and years of playing the points game.

• I’ve built this arsenal of CCs over more than a decade, never opening more than one new card per year, maintaining a rock-solid credit score throughout.

• I’ve redeemed points for countless flights, including frequent transcontinental business class flights, which is a treat that always feels like mastering the art of the sign-up bonus is worthwhile.

• I’m currently primarily loyal to Delta, with United as my second choice carrier.

• My CC spending skews heavily toward travel, dining, and occasional big-ticket purchases.

Your “right” lineup may look very different depending on where you live, who you fly, and how often you travel. But, let’s see, shall we?

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Last Sunday’s letter, The 26 small upgrades that make my everyday life a whole lot better also took on a life of its own this week, now having reached 12k+ readers and counting. Y’all reallyyyyy seemed to especially enjoy my section on wearing actual pants to the airport (!!), with dozens joining me as proud members of the sweatpant jeans club. I’ll be sporting mine on my flight to LAX next Sunday, so it seems fitting!

• What feeds creativity

• What kills creativity

• The Vault (Paid Subscriber Exclusive): What creativity looks like in this season of my life

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Today’s letter focuses on a topic I ruminate on often: what feeds creativity, and, conversely, what kills it. Each January 1st, I queue up my audiobook of Big Magic: Creative Living Beyond Fear by Elizabeth Gilbert. It’s a quick listen—just about 3.5 hours—and despite this being my fourth time revisiting it, I continue to take away new tidbits.

Gilbert (yes, the Eat Pray Love one, but also, so much more!) approaches creativity less as something you summon and more as something you host. A presence that shows up when it feels welcome—and quietly disappears when it doesn’t. She treats ideas as living autonomous entities, and the incredible story she shares about an idea that came knocking at both her and Ann Patchett’s door is reason enough to read the book.

Her approach poetically reframes creativity not as something that requires suffering or genius, but as a force that welcomes curiosity and play. Her central idea that fear is allowed to come along for the ride, but not be in the driver’s seat, has a way of sticking with you. Coming off this latest re-read, I felt compelled to summarize what tends to feed my creativity in general and what reliably shuts it down. Consider this less advice, more an inventory—ingredients to check your creative pantry for in 2026.

But first, a broadening of your definition of “artist.”

In Big Magic, Elizabeth Gilbert is careful to define creativity broadly. “Art” isn’t limited to writing books or making art in the traditional sense; it’s any act driven by curiosity rather than obligation. Creativity shows up in how you solve problems, how you host a dinner, how you build a business, and ultimately, how you make meaning out of everyday life. Basically, whether or not you know it, you are an artist.

Curiosity over outcome.

Creativity thrives when the question is “What am I interested in?” rather than “How will this be received?” Outcome-driven thinking tends to constrict and manipulate things before they’ve had a chance to unfold. Curiosity, on the other hand, creates room for exploration without expectation.

Low-stakes creation.

The kind of making that isn’t trying to become anything is often where the most meaningful projects begin: an idea jotted down on the back of a napkin, knitting a garment knowing it’s not going to be perfect, a watercolor that quite literally goes outside the lines. Gilbert reminds us that creativity doesn’t need pressure to survive—it needs the opposite. Lower the stakes, and the work begins to breathe.

Creating before consuming.

Creativity often needs a moment of quiet before it can make itself known. Beginning the day without taking in other people’s ideas is the surest way to actually give your own a chance to surface. When the metaphorical room is already full, it’s hard to hear what an idea is trying to tell you. Not to mention, the sheer hours we spend (waste?) on scrolling and consuming take away from the practical possibility of carving out time for art. Personally, this category presents my largest area of opportunity to shift how I’m operating.

Don’t expect your art to pay your rent.

In Big Magic, readers are reminded that creativity struggles when it’s asked to be everything at once—meaningful, profitable, and identity-defining. There’s a difference between making money from creative work and asking that work to sustain you, financially or emotionally. When art is relieved of that burden, it stops negotiating and starts offering. Ideas tend to arrive more freely when they’re invited, not depended on.

Pursue creative cross-pollination.

Creativity expands when it’s allowed to borrow language from elsewhere: reading outside your usual genre, visiting museums unrelated to your medium, talking to people who don’t do what you do. These moments of newness spark inspiration and introduce new textures without demanding output.

Give yourself permission.

The radical idea that you’re allowed to make things simply because you want to is a huge step in embracing your creativity. Not because you’re an expert. Not because you’re ready (what does that even mean, after all?). Just because you’re curious.

Waiting for the confidence.

Confidence is not the prerequisite; it’s the byproduct of actually doing the thing. In Big Magic, Gilbert is clear that creativity doesn’t wait for certainty before showing up. Waiting to feel ready often means waiting indefinitely. Remember, “ready” isn’t a feeling—it’s a decision.

Over-identifying with the work.

When output becomes a proxy for your worth, creativity gets stage fright. Suddenly, every idea feels like a referendum rather than an experiment. The work tightens under the pressure of having to represent who we are as people. There’s something quietly romantic about having a private creative outlet—one that exists without witnesses, fueled in the margins of your day, owing nothing to anyone else.

Turning creativity into a performance review.

Metrics, optimization, comparison—all useful tools, but terrible muses. When the work is constantly assessed for effectiveness or reach, experimentation narrows. Creativity struggles when it’s treated like a quarterly report. It’s difficult if your outlet involves any level of external readership or viewers in order for it to exist in the world to step away from the analytics; in my case, for instance, with TSS, I want people to read and interact with it! But just because a post doesn’t get “engagement” actually doesn’t mean the writing was any less valuable to me as the creator.

Perfectionism dressed up as “high standards.”

The one that masks as responsible, even virtuous, but is often just fear with better branding. As a lifelong ‘perfectionist,’ I’m making an active choice to be rooted in “done is better than perfect” with all I create. Ideas rarely survive long enough to become themselves in environments where we are hypercritical, so sometimes, the freedom that comes from simply finishing something (even when you know it could be better) is the ultimate embodiment of creativity.

In this season of life, my creative well feels closely tied to the tension I’ve learned to sit with between expansion of self and protection of self. On one hand, I feel a genuine pull to create more—to experiment with new formats, to make silly TikToks, to show up more visibly and honestly. On the other hand, I’m deeply aware of the stability my full-time job provides, and how much peace and, in turn, steadiness it affords me. I’m not willing to post or share anything that would threaten that.

For a long time, I thought this meant I had to choose—either protect the structure I’ve built at all costs, or risk it in service of creative expansion on my personal projects. These days, I’m clearer than ever about the possibility that sits in the middle, having finally found the boundary between the two. I know how to pour my creative energy into both the job that allows me to move through the world the way I do and the content I create, separate from that.

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My energy coming into this year is especially supercharged thanks to the meaning I put into numerology. If we aren’t yet connected on Instagram (let’s fix that!), it might be news to you that 26 is my angel number. If you’re not familiar, angel numbers function as a cosmic nudge—when I see mine pop up in a licence plate, street address, or something as menial as a coat check ticket, it feels like the universe’s quiet reminder that I’m on the right path. That being said, kicking off 2026 feels like one big call from the universe. I actually got the below text from my mom months ago and felt so seen…this year is calling to make it count.

All this numerology and goal-setting talk brings me to the topic of this issue: upleveling your life in both little and big ways. When journaling this past week, rather than making sweeping resolutions or reinventing the wheel, I found myself looking back at what already worked this past year—the ideas that resonated most, the small upgrades that quietly improved my days, and the cultural corner of the internet I’ve been spending my time in lately. Consider this first TSS edition of 2026 a snapshot of what carried me through last year, and what I’m bringing with me into the next 365!

• My most engaged 10 letters of last year

• The 26 little upgrades that have made my life better

• The Vault (Paid Subscriber Exclusive): What I’ve been watching, reading, and listening to these days!

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Every year, I’m fascinated by what content rises to the top—not just in terms of numbers, but energy. What people save, forward, and reply to. What lands in inboxes at exactly the right moment. Looking back at last year’s most engaged letters (this reflects a combination of open rates, click-throughs, replies, saves, forwards, and conversions to paid subscriptions), a few clear throughlines emerged, revealing not just what I loved writing, but what you loved reading. For your perusing pleasure, the top ten are listed and linked below.

1. 88 *NICHE* Gift Ideas for Very Particular People. 8 hyperspecific guides for the hotel snob, the ultimate hostess, the voracious reader, the frequent flyer, the Francophile and more!!

2. A No-Gatekeeping Guide to Mallorca. Reporting back from my fourth stint on this magical island...

3. Little Luxuries that Make an Outsized Impact. 26 ways to romanticize the everyday.

4. A Week in My [Charmed] New York City Life. work, play, West Village Book Club, and everything in between (with timestamps)

5. Sun, Sea, and Reverie: The Magic of €uro Summer: including my breakdown of the four Balearic Islands and a mini Formentera Guide

6. How to Romanticize Your Life (according to self-proclaimed experts) which was a fun collab with my friend !

7. Your Local’s Guide to West Village ...112 places that prove it is indeed, good to be a West Village Girlie

8. The Packing Method that Changed My Life (written while packing a carry-on for 12 days to Australia) including the exact AI prompts I use to pack like a pro

9. I’m Gifting $450 of Goodies to Celebrate International Women’s Day. plus, Q&As with Dianna Cohen and Laney Crowell

10. 2025 Intentions: to get HOTTER and RICHER. do I have your attention yet?

For this section, I really wanted to be less shoppy and more ‘optimize your life’ vibes, but the reality is, a fair bit of these upgrades do involve replacing an everyday item with a better one. Luckily, most are less than $100!

Traded in running and light sculpt workouts for lifting heavy. This one was a colossal shift considering I ran 500+ miles and pulled off a marathon PR in 2024, yet I started the year pretty unhappy with how I was feeling physically. Oh, the irony!!!!! I decided to swing the pendulum in the complete opposite direction and started weight lifting a few times per week. A total game-changer, not necessarily in the number on the scale, but in the composition of my body, I’m excited to keep this habit up in 2026.

Replaced my electric toothbrushes with this Swiss-made handheld toothbrush. I love the idea of going analogue in as many aspects of life as possible, and after losing my second electric toothbrush in a hotel room, I decided to go back to basics. I fell in love with this brand after being given one as a dental amenity kit in Zurich and haven’t looked back since.

Swapped my fridge water filter dispenser. This 20-cup dispenser filters out metals, minerals, salts, and ions and has a TDS meter to check the levels of dissolved solids before dispensing or pouring water, so you always know when it is time to change your filter! I especially like how it sits in my fridge and is easy to refill without taking it out.

Speaking of water filtration: installing my Jolie Filtered Shower Head. The IG ads finally got me on this one and it’s so worth the hype! Can’t believe I waited as long as I did to make this switch. So easy to install and replace the filter regularly.

Being a late adopter of Salomon XT-Whispers. I wasn’t cool enough to wear these before they were mainstream, but now I’m on my second pair and fully hooked on finding fun colorways before they sell out (the cool colors always sell out).

Caved on a vibration plate. Again, TikTok got me bad on this one, but I’ve loved incorporating this into my morning routine for enhanced muscle activation, improved circulation, and faster workout recovery. Vibration plates are also supposed to help with bone density and lymphatic drainage.

My Kindle. My sissy got me my Kindy (as we lovingly call her) for Christmas last year after years of me insisting I preferred paperbacks/hardcovers. Now, I can’t imagine NOT having her, especially for travel!

GIN GINS when feeling car sicky. These are another must add to the travel bag; anytime I’m on a long drive, these are a savior.

Speaking of travel bag…creating a permanent travel toiletry kit. No more decanting products into mini bottles or scouring through my toiletries at midnight before an early morning departure. Everything lives packed and ready, and I just restock when I get home. It’s one of those systems that makes me feel very adult!

Swapped my Armani foundation for Victoria Beckham foundation. I hate to be this person, but this product is worth its weight in gold…easily my top beauty product upgrade of the year. It goes on more like skincare and stays on so well throughout the day. I feel like my skin has only gotten better since I started using it, and you barely need a pea-sized amount of product to make a huge impact. VB doesn’t sell at Sephora, but ’s Violet Grey has her products! FWIW, I’m shade Fair 3 Light.

Mixing protein powder into my yogurt. We are all so inundated with the need to consume more protein, so this is just a little cheat! I mix a scoop of this brand into my Fage (which I get unflavored) nearly every morning.

Becoming a Russian manicure person. Possibly the beauty treatment that revolutionized my year in the most impactful way, I finally started going once a month for an e-file manicure at Yara, and I cannot believe how much my nails have gotten longer and stronger. If you have a salon near you that does this style of mani, run, don’t walk. I can even stretch to five weeks in between appointments when needed, and my nails have never looked better!

Getting a cross-body pearl phone chain. Before my work trip to Australia, I decided to get this and it made having my phone handy during long travel days and while on the trip to shoot content such a breeze. Mine is currently on sale.

LMNT electrolytes. I’ve tried basically every electrolyte brand on the market and these are the best IMO. Always have them in my travel bag!

Replacing my old lip mask for the TATCHA Kissu lip mask. Coming from a Rouge Sephora girlie, you can trust I do my fair share of product sampling! This was one of my fave totally unnecessary but totally fabulous upgrades of the year. Also make great gifts!

This handheld steamer. Again, I used this brand at a hotel and immediately knew I needed to upgrade my steamer at home.

LUMIFY eye drops. IYKYK and if you don’t, now you do! Nothing will make you look more alert and polished than a few drops of Lumyyy.

Clean Skin Club Face Pads and Face Towels WOW. I’m obsessed with these. I grew up in a washcloth house…there were always so many washcloths in the laundry between my sister, my mom, and me, and I carried that habit into adulthood of always needing a washcloth to wash my face. Turns out, these disposable towels are much more hygienic!

Cocolab floss. I’ll admit I’m not great at flossing. This is the lovliest brand I’ve ever used and my best chance at actually flossing!

Began using Biodance Bio-Collagen Masks. Me and the rest of the internet adore these Korean masks. I personally don’t like sleeping in them but prefer to put one on around 6p or so and take it off around 9p; your skin is literal glass afterwards.

Starting my day with my Theraface Depuffing Wand. Always in my travel bag and lately when home, I’ve been doing this while on my vibration plate to habit stack and it’s a fun way to really feel snatched to start the day. Nothing feels as good as this cool applicator on puffy eyes!

Using the Hatch Alarm Clock instead of my phone. The Hatch was the top-selling product on my holiday gift guide, and with good reason! What a gorgeous way to start the day, versus having your phone beside your bed.

No more leggings on flights. Real pants! But comfortable pants!!! I love these ones and these ones (worth the splurge). Or, if you want to pull off pants that look like jeans but are actually sweats, of course, these ones. Having a go-to “airport uniform” changed how I feel starting a trip and how I show up when I land.

Becoming a belt person. Belts became my hyperfixation this year, beginning with acquiring my Ralph Lauren Metal Accent Leather Belt, as well as building up my Aureum collection (shoutout !), including this one, this one, and this one to name a few. These belts instantly make an outfit look more elevated, and I’m looking forward to continuing to cultivate my collection. Next one on my wishlist is this beauty! Also, I take mine to my shoe guy to add extra holes so I can wear high-waisted or at the hips.

Allowed myself to have a scale for the first time since college. Well, well, well, if I’ve seen a better reason for a paywall, then I haven’t met her yet. Body image/weight is such a personal topic, so thank you for the grace to open up a bit about my [fraught] relationship to it.

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Hello, bookworms!

Since launching The Sunday Series in 2020, my annual reading roundup has become a TSS staple. For the past five years, I’ve used Goodreads to track my reading, both setting a reading goal for the year and using the platform to look back and jog my memory on which titles left the biggest impression. Some years I’ve fallen short of my reading goal, but this year, I managed to polish off 62 titles!

• In 2025, I read 62 books.

• In 2024, I read 56 books.

• In 2023, I read 56 books.

• In 2022, I read 52 books.

• In 2021, I read 37 books.

Which brings us to the purpose of today’s edition of my annual reading roundup: I’m sharing the 25 books that stood out to me most this year. Plus, exclusively for paid subscribers, I’m looking back at over 300 books read in recent years and rounding up 75 of my top reads, making this a robust reference of 100 total books you can dive into with absolute confidence—that is, if we share the same reading taste! Before you dive in, a quick note on the lens with which I pick books…

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At all times, I’m reading something fiction and something nonfiction. But I consume them differently. When it comes to fiction, I read all of my books in physical form, whether that be hardcover, paperback, or Kindle (a new addition to my rotation in the past year). For nonfiction, I listen via Libro.fm, the Libby app, or Spotify. I particularly love listening when the author is the narrator of the audiobook, as most often is the case for memoirs, which just so happen to be my most sought-after nonfiction genre.

When it comes to fiction, I’m drawn to complex women, messy friendships, complicated family dynamics, ambition, secrets (did someone say double life/hidden family??), and reinvention, with a particular soft spot for upmarket fiction and literary suspense. If there’s sharp social commentary, a beautifully rendered setting, or a twist that feels inevitable in hindsight, even better. I’m also a sucker for an unlikeable narrator and mulit-POV novels that really get you in the head of the storyteller.

With nonfiction, I’m most compelled by voice. I love memoirs and essays that feel intimate, self-aware, vulnerable, and culturally attuned—books that explore identity, creativity, power, pleasure, food, work, media, and modern relationships through a personal lens. I tend to favor writers who are thoughtful without being precious, reflective without being didactic, and who make you feel like you’re in conversation with them rather than being taught a lesson. I particularly gravitate towards memoirs set in New York.

Okay, let’s get into it!!! If there’s an asterisk, that indicates it was a pick. In case you’re new here, I launched WVBC in 2022, and we collectively launched our book club Substack on January 1st. In it, each month, the six of us round up a review of our meeting and recap what we each read. Subscribe below if you’re interested…we have some fun stuff coming in 2026!!

West Village Book Club

six voracious readers sharing their book recs, book club hosting tips, and love for New York City

By Kayla Douglas

• All the Colors of the Dark by Chris Whitaker (2024)* | This was a WVBC pick earlier this year, and we all were drawn into this heart-pounding literary thriller that manages to blend gritty suspense with gut-punch emotion. It’s a longer read, but it paces quickly! FWIW, we all finished the 500+ pages, which says something.

• The Art of Vanishing by Morgan Pager (2025)* | A smart literary novel about a woman who discovers she can actually enter the paintings in the museum where she works. Pager explores art, love, and longing through a quietly surreal lens, using the museum as a space for both escape and self-reckoning. Thoughtful, inventive, and emotionally restrained.

• The Blue Bistro by Elin Hilderbrand (2005) | I picked this one up ahead of our Nantucket trip because its beachfront restaurant was inspired by Galley Beach, a spot we dined at in June. This quintessential Nantucket novel combines romance, reinvention, and all the drama behind the doors of an iconic seaside restaurant. Written in 2005, it was fun to do one of Hilderbrand’s backlist books!

• Blue Sisters by Coco Mellors (2024) | Easily one of the most touching stories I’ve read in years, this one is about three estranged sisters reuniting in the wake of tragedy. Mellors’ sophomore novel delivers a sweeping, stylish family drama about grief, identity, and love. I loved her writing style so much that I ran out to get her debut (on my list below) right away.

• Broken Country by Clare Leslie Hall (2025) | Easily one of the best books I’ve read in recent memory, this sweeping second-chance romance is an atmospheric dual-timeline novel set in mid‑20th‑century UK countryside. It follows Beth—a farmer’s wife—whose quiet marriage begins to unravel when her teenage first love, Gabriel, returns to town with a young son. Their reconnection reopens old grief, sparks a love triangle, and culminates in a gripping murder and courtroom drama. I loved it for its emotional twists and murky moral terrain!

• Cleopatra and Frankenstein by Coco Mellors (2022) | A messy, modern love story about a whirlwind marriage between a British painter and an older, successful American man in New York City. Mellors captures intimacy, power imbalance, and emotional dependency with brutal honesty, making this a sharp portrait of how love can both save and slowly undo you. Complicated, stylish, and deeply human.

• The Correspondent by Virginia Evans (2025) | A clever, voice-driven novel told through letters, emails, and professional exchanges that reveal the quiet interior life of a woman whose job is to stay observant—but emotionally removed. As her carefully structured world begins to crack, the book becomes a meditation on loneliness, connection, and the stories we tell (or withhold). It had me sobbing on my flight home from Sydney!!!!

• Discontent by Beatriz Serrano (2025) | A darkly funny, sharply observed novel originally written in Spanish and translated into English about a woman unraveling under the pressures of modern work, capitalism, and emotional burnout. Serrano skewers corporate culture and personal dissatisfaction with biting wit, making this feel both painfully specific and uncomfortably universal. Perfect if you like your social commentary with teeth.

• Heart the Lover by Lily King (2025)* | A quiet, emotionally precise novel about longing, betrayal, and the complicated aftermath of love that doesn’t resolve neatly. King excels at interiority here, tracing how desire and restraint coexist within long-term relationships. It’s tender, thoughtful, and devastating in a very restrained way. I hosted WVBC last month when this was our pick and had so much fun gathering our crew to discuss it!!

West Village Book Club

WVBC monthly: chapter 11

Hi, dear readers…

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5 months ago · 8 likes · 2 comments · Kayla Douglas

• Once and Again by Rebecca Serle (2026) | Out in March, I got my hands on an early copy of this time-bending love story that explores fate, grief, and the possibility of getting a second chance at a life-defining relationship. Serle blends romance with her classic magical realism in a way that feels grounded rather than gimmicky. If you like emotional what-ifs that make you reflect on timing and choice, this one hits.

• Mansion Beach by Meg Mitchell Moore (2025) | A reverse Great Gatsby, I’ve been recommending this beach read to so many friends. Set on Shelter Island, sun, sand, and simmering secrets collide in this sharp coastal drama about privilege, ambition, and the price of reinvention.

• Set Piece by Lana Schwartz (2025) | A modern second-chance romance set on a movie set, following a breakout TV star and the no-nonsense production designer he once fell for—back when she was bartending. When their paths cross again years later, chemistry reignites, complicated by fame, motherhood, and very real adult baggage. Breezy, romantic, and a quick, fun read.

• The Tenant by Frieda McFadden (2025) | A fast-paced psychological thriller that wastes no time pulling you into a web of suspicion, secrets, and escalating paranoia. As a seemingly straightforward rental situation turns sinister, McFadden delivers twist after twist that makes this incredibly bingeable. Perfect if you want something propulsive and addictive.

• Wild Dark Shore by Charlotte McConaghy (2025)* | A haunting, atmospheric novel set on a remote coastline on a fake island between Antarctica and Tasmania, where isolation amplifies grief, family bonds, and environmental threat. McConaghy blends literary prose with mounting suspense, creating a story that feels both intimate and expansive. Nature plays a central role here, almost as a character itself.

• The Women by Kristin Hannah (2024)* | A powerful historical novel about women who served as nurses during the Vietnam War, told with Hannah’s signature emotional sweep. This book shines a light on a group long overlooked in war narratives, exploring trauma, friendship, and resilience. It’s heartbreaking, absorbing, and deeply human.

• Care and Feeding by Laurie Woolever (2025) | I just finished this book this week and am sure it’s going to stay with me for quite some time. Woolever’s sharp writing paints a moving portrait of food, grief, marriage, cheating, and life after loss. Her work with both Mario Batali and Anthony Bourdain as a longtime collaborator puts equal parts candor and heart into this story.

• Careless People: A Cautionary Tale of Power, Greed, and Lost Idealism by Sarah Wynn-Williams (2025) | A revealing memoir from a former Facebook insider that chronicles the company’s early idealism—and its moral unraveling. Wynn-Williams offers a clear-eyed look at power, tech culture, and the personal cost of working inside one of the most influential platforms of our time. Disturbing, fascinating, and hard to put down.

• More: A Memoir of Open Marriage by Molly Roden Winter (2024) | A raw and riveting deep dive into love, desire, and the complexities of non-monogamy—this memoir is equal parts confessional and cultural critique. It was my first time listening to such a detailed chronicle of an open marriage and definitely kept me sucked in at a level that’s difficult for a memoir written by a ‘regular person’ (versus a celebrity).

• The Tell: A Memoir by Amy Griffin (2025) | This book was all over the internet earlier this year, and with good reason. Griffin, a high-achieving investor and mother of four, honestly depicts her journey facing deeply buried childhood trauma as she uncovers an assault while undergoing a controversial MDMA-assisted therapy session. She uses this experience to explore themes of ambition, perfectionism, healing, and what happens when secrets unravel decades later.

• We Are Experiencing a Slight Delay: Tips, Tales, Travels by Gary Janetti (2024) | If you’re new around here, this one is a bit biased as Gary is a friend of West Village Book Club and someone I’ve been able to collaborate with professionally, but funny enough, this book was my entry point to getting to know him! It’s hilarious, biting, and self-aware, as he infuses his signature wit into recounting travel stories spanning decades.

I think of the below grouping less as standalone memoirs and more as a case study of a cultural era—specifically, the glossy, ego-driven, wildly influential world of American media from the 1980s through the early 2000s, and its long afterlife today. These books trace how taste was made, how power circulated, how ambition was rewarded (or punished), and how entire cultural narratives were shaped by a relatively small group of people with outsized platforms.

• The Vanity Fair Diaries: 1983-1992 by Tina Brown (2017) | A front-row account of Tina Brown’s rise at Vanity Fair, capturing the excess, ambition, and cultural dominance of magazines at their peak. Equal parts gossip, strategy, and self-mythology, this diary reads like a masterclass in power and taste-making. Essential context for this entire media-era grouping.

• When the Going Was Good: An Editor’s Adventures During the Last Golden Age of Magazines by Graydon Carter (2025) | This irresistible peek into glossy magazine culture showcases the Vanity Fair days at their peak—full of name-dropping, mischief, and the unapologetic glamour of a bygone media era. Would be a good one to read following Tina Brown’s memoir!

• Empire of the Elite: Inside Condé Nast, the Media Dynasty That Reshaped America by Michael Grynbaum (2025) | A deeply reported cultural history of Condé Nast and the people who shaped its mythos. Grynbaum traces how influence, aesthetics, and hierarchy operated behind the scenes, offering a more analytical counterpoint to the memoirs in this section. A must-read for understanding the machinery behind the gloss.

• Joyride: A Memoir by Susan Orlean (2025) | A charming, reflective memoir that blends personal storytelling with Orlean’s signature curiosity about people, passions, and obsession. Moving fluidly through her life and career, she explores what it means to stay open to wonder over time. Warm, thoughtful, and quintessentially Orlean.

• I Regret Almost Everything by Keith McNally (2025) | Another epic memoir from the hospitality world, this unapologetic, darkly funny tell-all comes from the legendary restaurateur behind Balthazar and chronicles the chaos of New York dining and a life lived loudly. For anyone who appreciates the NY dining scene, I think this is a must-read. The impact his stroke had on his business, marriage, and writing life is particularly poignant.

Exclusive to paid subscribers, I’m now thrilled to roundup a backlist of my top 50 fiction picks and top 25 nonfiction picks beyond what I read this year.

• 28 Summers by Elin Hilderbrand (2020)

• Adelaide by Genevieve Wheeler (2023)

• All the Light We Cannot See by Anthony Doerr (2014)*

• Black Cake by Charmaine Wilkerson (2022)

• Bright Young Women by Jessica Knoll (2023)

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Hello from midnight on Summer (!!) Solstice eve, friends!

What more poignant place to be writing to you than from my Park Hyatt Sydney balcony overlooking the Sydney Opera House? Spoiler alert: this hotel just made it onto my fifty-five best stays of all time list.

If the very existence of this list is news to you, let me provide some context. Last December, I published my first installment fresh off a frenzied week of work-meets-raucous-fun, also known as ILTM Cannes. This year, I’m checking in with you on a whole different kind of high—the one I get from checking off somewhere on my personal bucket list. I’ve just spent the last ten days in Australia, and what a whirlwind it’s been. Stay tuned to ’s channels for more, because from my flight there aboard United’s inaugural San Fran to Adelaide to my check-in at Southern Ocean Lodge on Kangaroo Island, it’s been the trip of a lifetime—a phrase I certainly don’t use lightly.

In my role at SmartFlyer, I’m always in search of the next story—be it about the hottest new hotels set to open, bucket list trips that would make epic gifts for the person who has everything, or a local’s guide to Lower Manhattan, I’m constantly thinking in terms of what travelers are craving. And while I actively aim to keep my “work self” separate from The Sunday Series, the reality is, there’s no personal and professional separation between my deep appreciation for exceptional hospitality. So, here we are…talking about some of the experiences that have left their mark on me this past decade, plus a hundred more I’m dreaming about that I think you’d love too.

But, how did a girl from a rural upstate New York town wind up here with the chance to experience some of the world’s best hotels? During my last 10+ years working in the travel agency space, I’ve been fortunate enough to take research trips, attend events, and indulge in more than a few vacations across the U.S., Mexico, the Caribbean, South America, Europe, Africa, Asia, and now, Australia. I’m motivated by the act of constantly changing my environment and seeing how, in turn, it changes me.

So, as I look ahead to 2026 travel plans, I thought that this recap of fifty-five (sorry for the random number, but I really couldn’t narrow the list any further) of my most memorable hotel stays ever could help spark some inspo for your upcoming travels. Plus, for paid subscribers, I’m also rounding up 100 hotels around the world that I’m dying to check out. Of course, every single stay on this list would be enhanced by the perks that come with booking with a travel advisor. So if you ever find yourself needing one, I’m close with dozens of savvy agents and am constantly matching acquaintances and friends with different experts based on their personalities and destination interests. So, you know where to find me if you’d like an intro! xKD

For so many of us, travel planning starts with a place on the map: a country, a city, a coastline. But over time, I’ve found that the most memorable trips often unfold the other way around—beginning not with a destination, but with a hotel. The right property can shape the entire rhythm of a journey: how long you stay, how you move, what you prioritize, and most especially, how you connect with people and place while you’re there. These are the kinds of hotels that don’t simply anchor a trip; they define it.

When brainstorming which properties would make my list, I had a few stipulations in mind. For me, it’s not always about the buzziest hotel. In fact, I’ve stayed at several that garnered spots on the World’s 50 Best list, but that didn’t personally resonate, and in turn, won’t be listed below. Instead of award credentials, I’m seeking places that afford you the chance to sink into a sense of timelessness. I adore a property that feels like it’s always been there—wherever ‘there’ is. Exemplary service and impeccable design go without asking, but first and foremost, it’s a feeling of belonging I’m after when I check into a hotel.

After much deliberation, here are fifty-five check-ins that are near and dear to my heart. In no particular ranking order…

1. The Carlyle, A Rosewood Hotel (New York, New York)

2. Aman New York (New York, New York)

3. Four Seasons Hotel at the Surf Club (Surfside, Florida)

4. Rosewood Miramar Beach (Montecito, California)

5. The Lodge at Blue Sky, Auberge Collection (Wanship, Utah)

6. Cap Juluca, A Belmond Hotel (Anguilla)

7. Malliouhana (Anguilla)

8. Hacienda AltaGracia, Auberge Collection (Santa Teresa de Cajón de Pérez Zeledón, Costa Rica)

9. Las Ventanas al Paraíso, A Rosewood Hotel (Los Cabos, Mexico)

10. Esperanza, Auberge Collection (Los Cabos, Mexico)

11. Maroma, A Belmond Hotel (Riviera Maya, Mexico)

12. The Dorchester (London, England)

13. The Chancery Rosewood (London, England)

14. Monasterio, A Belmond Hotel (Cusco, Peru)

15. La Réserve Paris Hotel & Spa (Paris, France)

16. Four Seasons Hotel George V (Paris, France)

17. Hôtel Plaza Athénée (Paris, France)

18. Le Meurice (Paris, France)

19. BULGARI Hotel Paris (Paris, France)

20. Carlton Cannes, A Regent Hotel (Cannes, France)

21. Hotel de la Ville (Rome, Italy)

22. Portrait Firenze (Florence, Italy)

23. Villa Igiea (Sicily, Italy)

24. FORESTIS (The Dolomites, Italy)

25. Cipriani, A Belmond Hotel (Venice, Italy)

26. Mandarin Oriental Ritz, Madrid (Madrid, Spain)

27. Six Senses Ibiza (Ibiza, Spain)

28. La Residencia, A Belmond Hotel (Mallorca, Spain)

29. Grand Hotel Son Net (Mallorca, Spain)

30. Hotel Can Ferrereta (Mallorca, Spain)

31. Finca Cortesin (Costa del Sol, Spain)

32. Marbella Club (Marbella, Spain)

33. Four Seasons Astir Palace Hotel Athens (Athens, Greece)

34. The Gleneagles Hotel (Auchterarder, Scotland)

35. Rosewood Schloss Fuschl (Lake Fuschl, Austria)

36. Hotel Sacher Vienna (Vienna, Austria)

37. Four Seasons Hotel Prague (Prague, Czech Republic)

38. Four Seasons Hotel Gresham Palace (Budapest, Hungary)

39. Four Seasons Hotel Istanbul at Sultanahmet (Istanbul, Turkey)

40. MAÇAKIZI (Bodrum, Turkey)

41. Babylonstoren (Cape Winelands, South Africa)

42. Ellerman House (Cape Town, South Africa)

43. The Silo Hotel (Cape Town, South Africa)

44. Singita Lebombo Lodge (Kruger National Park, South Africa)

45. Singita Sabora Tented Camp (Serengeti, Tanzania)

46. Singita Faru Faru (Serengeti, Tanzania)

47. Kwessi Dunes (NamibRand Nature Reserve, Namibia)

48. Shipwreck Lodge (Skeleton Coast, Namibia)

49. Zannier Omaanda (Windhoek, Namibia)

50. Kasbah Tamadot (The Atlas Mountains, Morocco)

51. InterContinental Danang Sun Peninsula Resort (Danang Sun Peninsula, Vietnam)

52. Rosewood Hong Kong (Hong Kong)

53. Southern Ocean Lodge (Kangaroo Island, Australia)

54. Saffire Freycinet (Coles Bay, Tasmania)

55. Park Hyatt Sydney (Sydney, Australia)

WOW! It was so fun for me tweak this list off last year’s edition…I’d say it’s changed about 20% in the past twelve months—a result of staying at a fair number of the places that were on my wishlist (it’s called MANIFESTING, and it’s actually the Winter/Summer Solstice today depending on where you’re reading this…) plus, taking new openings into account. Personally, I aspire to use the list sort of like I use my ‘Want to Read’ list on Goodreads. Meaning I try my best not to walk into a bookstore without at least consulting one of the hundreds of books I’ve already noted that I wanted to read. So, in the case of these 100 hotels, I’ll continue to refer to it as I plan future trips and try to work off the list versus always just flailing my way toward whatever hotel check-in comes next.

1. The Greenwich Hotel (New York, New York)

2. Hotel Jerome, Auberge Collection (Aspen, Colorado)

3. Amangiri (Canyon Point, Utah)

4. Post Ranch Inn (Big Sur, California)

5. San Ysidro Ranch (Santa Barbara, California)

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Hi, it’s meeeeeee! I’m that person. And you could be too. Which is why I’m here to share the method to my maddness.

Before we get into the ‘how’ it’s done, let me give you my credentials in case we don’t (yet!!) know one another. I’m Kayla, and I’ve worked in the travel industry for a decade and counting, with the vast majority of my most intrepid travels (Sri Lanka, Vietnam, Namibia, Tanzania, South Africa, Peru, etc, etc) involving some type of work component.

And over those precious years tightening up my travel method, I’ve developed a severe aversion to being the person who:

• holds up a group airport transfer waiting at baggage claim when others carried on

• misses a flight because I’ve hit insane traffic on the way to the airport and in turn, doesn’t make the STRICT cutoff time to check a bag…a time constraint I know all too well after a curfuffle on the way to Mexico City that required my most persusive begging of an airline employee ever for me and my bag to make it to CDMX!

• has a checked bag wheel *break* while in the hands of the airline and is then stuck hefting a broken suitcase around (see below)

• has their checked bag lost by the airline and is without 80% of what they need for the duration of a trip (dear reader, note that this has unfortunately happened to me…in combination with getting the suitcase back three days later and broken!!!!!)

• has to pack and repack multiple bags and bring said bags on multiple legs of a journey, in turn feeling like a chaotic caravan rather than a human person!

As you can see by the photos and scenarios described above, the truth is, sometimes, I check. Sometimes I even send a suitcase ahead of time if I’m combining too many climates on an itinerary and don’t want to be burdened by checking for the entire trip. I used this method this last year during a six-week trip combining Colombia, France, and Italy, and it saved me.

Another example of a trip I’d check for? In the spring, I’ll go to Japan and Korea for work and absolutely plan to check because I plan to shop…how the heck could I not account for wanting to bring back vintage from Tokyo and skincare products from Seoul? I share this all because I’m not CRAZY. There is a time and place for checking, of course.

But, for the most part, I really aim to simplify my life by being a carry-on queen. I’m happiest when it’s just me and my Rimowa gliding through a terminal, not the least bit concerned about ‘whether my bag is going to make it.’ Of course, summer trips are ideal for this, and while we might be far from summer in the Northern Hemisphere, on Thursday, I’m headed Down Under (!!!!!) and was inspired to share with you how I’m prepping for it in real time. So, below I’ve outlined my entire system, step by step, including the ChatGPT prompts I use so you can replicate my method!

Additionally, if you want to check out all my go to travel products including the bags I use, my exact monogrammed packing cubes (on sale right now!!), tech organizer, and travel sized toiletries, everything is linked on my ShopMy.

my ShopMy

If you’d like to access the complete version future posts, please consider upgrading your subscription! Paid subscribers of The Sunday Series unlock an exclusive section of paywalled content in each send, access to the full archives (including Your Local’s Guide to West Village, A No-Gatekeeping Guide to Mallorca, A Mini Formentera Guide, Your Ultimate Paris Guide, Your Guide to Bozeman, Your Guide to Nantucket, 100 Hotels I’m Dying to Check Into, My Holy Grail Rules for an Overnight Flight, 31 Ideas for Your Next Birthday Trip, A Playbook for How to Make Friends As An Adult, and 16 Prompts for a Personal Quarterly Review), the commenting feature on each post, exclusive giveaways, and more. Plus, your support directly helps ensure this newsletter can continue to grow! Subscriptions are $8/month or less than $7/month if paid annually—also known as less than one fancy Starb*cks order. But don’t let me be the one to tell you why you should upgrade! I’ll leave that to a fellow reader…

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Before the suitcase even comes out, I begin to envision my upcoming trip (type of activities, level of formality of dinners, climate, etc.) and do a full sweep of my closet and drawers. I physically touch everything. I pull the pieces I feel my best in—the ones I reach for instinctively in my everyday life. Ultimately, your real-life favorites know how to take care of you better than any “aspirational” dress you’ve been saving for someday, so my goal is never to buy a bunch of new things for a trip or pack stuff I don’t usually wear. I want to feel as myself as possible when traveling, and that starts with wearing my ride or dies.

Due to limited space in my apartment, I use my bed for this next step. I pull everything I’m loving at the moment and could envision potentially bringing. This initial pile should be outrageous. Mine always is. But it’ll give you the raw material to cull down and seek clarity later when editing becomes logical instead of emotional.

This is where ChatGPT/your AI method of choice becomes your meteorologist!!!!

Here’s the AI prompt I use:

I’m packing for a trip. Here is my itinerary with dates and destinations: [paste itinerary]. 
Can you give me a day-by-day weather overview for each stop, plus any packing considerations (humidity, rain, wind, elevation changes, etc.)?

Suddenly, you have an actual climate roadmap—not a vague idea.

Turn your weather results into a simple note in your phone. Include:

• climate summary by destination

• daily temps

• wind/humidity/sun considerations

• notes of activities or reservations to dress for

This becomes your grounding document throughout the next steps. Here’s a peek at what my Notes app looks like for this trip!

The game-changing step: get a blueprint!!!

Here’s the AI prompt I use:

Here is my itinerary and weather summary: [paste your note].

Based on this, can you tell me:
– How many daytime and evening outfits I realistically need?
– What categories of clothing I should pack (and how many of each)?
– What specific considerations I should keep in mind based on flights, climate shifts, activities, and dress codes?
– What items are likely unnecessary or redundant?

Optimize for versatility and keeping everything carry-on only.

Now, you’re able to return to your initial pile with clarity and your blueprint in hand. At this stage, I’m specifically looking at the categories of clothing I should pack, in which Chat tells me how many tops (in sections), bottoms, dresses, layers, shoes, and accessories to bring.

• Sort your clothes into the categories matching the above. All of a sudden, you may realize you have seven pairs of pants out when you only have room for three or four.

• Remove anything that’s not a top-tier pick. Back to the pants example, I had four different linen pairs out but had to edit down to two.

• Prioritize outlier items that can’t be reworn. Evening outfits tend to be the toughest to ‘rewear,’ especially dresses, but I do think if you’re going to commit to the carry-on life, you have to pare back on much of anything that’s a one-time wear.

• Respect the climate swings. I have so often wished I packed warmer, so this is the time to favor sweaters or scarves to layer on over that pair of heels you’d only pull out once on the trip.

Et voilà…your pile has dramatically shrunk!

This is the step that changed everything for me. Once you’ve edited down to a tight selection, you MUST try on every outfit you plan to bring and photograph it on your body. Why?

• Your decision-making becomes visual and objective

• You instantly see redundancies and gaps

• You avoid overpacking “just in case” pieces

• You arrive at your destination with a literal lookbook in your phone!!!!

• Getting dressed while on the trip now becomes effortless—you already solved the puzzle at home

I make an album on my iPhone titled [insert destination] OUTFITS and add each look. This step ensures everything works together and nothing sneaky ends up in the suitcase.

I’m not going to lie, shoes are one of the hardest categories to edit, but it is critical to our mission that you remain vigilant here! And as tempting as it may be to buy new shoes to get excited about, unless they are sneakers, that is against my religion because we can’t be risking an uncomfy shoe when we only have a few pair to pull from to begin with!

• 4-5 shoes max: sneakers that you can workout in, a functional/walking shoe, one or two pair of sandals, and an evening shoe.

• Accessories that transform outfits: scarf, belt, earrings

Ohhhhhhh this is always the fun part. I typically show up with three cosmetic bags of toiletries, so long as I’m not flying through the UK, where they are vigilant about the liquids in one bag thing (another reason to potentially check LOL). Rules of the road are:

• No full sizes

• Multi-use products only

• Travel meds in a micro-kit

I’ve written about and linked all my fave travel products (particularly for a warm weather trip) before! Check out this post.

Now we get down to brass tax! The edit done, it’s time to get going with packing cubes. The physical strategy:

• Roll soft items

• Fold structured pieces

• Heaviest pieces by the wheels

• Pack outfits togher

Your suitcase should feel like a filing system, not chaos. I’ve even go sofar as to put notes on top of each packing cube with what’s inside if I want to stay hyper organized and avoid having to unpack my entire suitcase on a trip that has multiple stops…aka every single one of my trips.

Basically, everything in this bag has to be filed away into a pouch. You have to find your own system there, but I can share mine visually with you thanks to a TikTok of mine filmed on the way to Austria that went viral. Amongst the 425k people who’ve seen this video, not all loved my method but I DO and that’s all that matters!

@curatedbykaylacarryon doesnt mean skimping on skincare though #skincareroutine #inflightskincare #inflight #frequentflyer #europeansummer #europetravel #overnightflight #redeye #skincaretips #traveltips #businessclass #luxurytravel @Caudalie @La Roche-Posay @StriVectin @Tommy John @BODYARMOR @Lunya

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It’s travel day! I suggest wearring your bulkiest pieces on travel day:

• heaviest layers

• largest shoes

• comfortable, re-wearable base layer

• compression socks, always.

Then, in my hand luggage, for overnight flights, I will have a packing cube with fresh clothes that I’ll change into after waking up, putting the old clothes into that packing cube.

Ultimately, packing in a carry-on isn’t about sacrifice—it’s about clarity. By the time you’ve photographed your outfits and built your weather brief, the guesswork disappears. You’re left with pieces you love, outfits you’ll actually wear, and the joy of traveling lightly.

If you want the follow-up installment, I can share my exact packing list for Australia, complete with links and why each piece made the cut. Let me know!!! xKD