The packing method that changed my life (written while packing a carry-on for 12 days in Australia)
including the exact AI prompts I use to pack like a pro
You know those insufferable people who use every excuse to brag about only having brought a carry-on for [insert far-flung trip]? That one you schlepped a checked bag for?
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.
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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!
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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