October 2024
Can ChatGPT pack your suitcase for you?
Welcome back!
Packing for vacation is a puzzle, and to solve it you need to discover the right combination of items that unlocks multiple outfits without packing too much. Too much choice on vacation is stressful and I used to believe that “vacation me” required a specific vacation wardrobe (false) or that being in a new location will suddenly make me want to wear that top I haven’t worn in years (also false).
Your vacation clothes do not need to deviate from everyday clothes. In fact, styling your most-loved items in a new place can give you a new appreciation for your wardrobe MVPs. My wearing behavior changes slightly — I tend to wear dresses more on vacation because they’re relaxing to wear at dinner — but my day-to-outfits are still the same top-worn seasonal items.
It’s easy to overpack for vacation because the temptation to have choices when getting dressed is high, but overpacking overwhelms you with options when you really just want is just to relax. And what a bummer to come home and have to unpack items you didn't even wear and/or regret not having left space for travel purchases or gifts.
The styling pros have some great tips for vacation packing — I highly recommend Ali Pew’s ‘My 5 Tips for Packing Light’ and Becky Malinsky’s ‘Lesson from Pacing at the 11th Hour’ — but I decided to see if ChatGPT could build my packing list for me to de-stress the pre-vacation process. I wanted to pack as little as possible while still having what I needed for several days of travel, and wear everything packed at least twice.
My ChatGPT prompt included our location itinerary, a list of scheduled events, and some general style guidelines based on what I normally wear this time of year. I requested a table with a daily breakdown of location, day and night temperature, and outfits for both daytime, pre-booked daytime activities and dinner.
In total, I ended up packing 35 items for a 12 day trip.
Final Items Packed, by Category
Items Worn, by Percentage of Vacation Days
88% of the items I packed for vacation were worn at least once on the trip, with only 4 items not worn at all.
33% of items packed being worn more than twice.
Top worn items during the trip included my Nike Daybreak sneakers (always wear your heaviest shoes on the plane), my favorite lightweight TOTEME sweater, and a pair of low heel Gucci sandals that are wildly comfortable.
The unsung hero of the trip (and most trips) was this Tory Burch printed windbreaker that I wore 50% of vacation days, and scooped up at a steep discount a few years ago. It’s perfect for traveling because it’s lightweight and barely wrinkles and it’s easy to roll and shove in a bag, it has a hood in case it rains (I hate carrying an umbrella), and it has tons of pockets. It’s an item that I rarely wear in my day-to-day life but gets a lot of wear when I travel. I have the matching midi dress that I found on resale this Summer and wore them together twice during the trip with low silver heels.
ChatGPT saved me a lot of time and mental energy trying to solve the packing puzzle, and next time around I will continue to edit down items even more to pack less and get more vacation wears per item.
And with that, let’s take a look back at September.
What I Bought Last Month
While on vacation I took a peek in the Prada store, and ended up buying this absolute gem. Mrs. Prada is known for skirts - she wears a lot of skirts herself - but the pleated skirt is a house specialty. No regrets.
What I Sold Last Month
Nada, but I’m planning to do another closet audit when my sister visits this month.
Most Worn Items Last Month
The trip really shook up the monthly most-worn data, but a lot of the monthly regulars are still in there.
Before you bounce I’d love to hear from you about the topics you’re interested in for the future. <3
See you next month!
Lauryn
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🛒 You may have noticed some affiliate links, which I may earn a small commission from. These are not to encourage you to buy (you probably already have something great in your closet!) but instead link to actual products I buy and love because it’s important to me to cite my sources.
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I love the name of your Substack/content focus! 😍 I’m curious—did using ChatGPT change your perception of what you ‘needed’ to bring versus what you might have instinctively packed? It’s so interesting how tools like this can challenge our usual habits and help us prioritize. I loved seeing the breakdown of what you actually wore versus what stayed in the suitcase—it’s such a great reminder of how our habits shift when we’re in a different environment. It’s funny how some pieces become our go-tos, even when we pack others with good intentions!