Why I Wear the Same Outfit Every Day on Vacation
My perfect holiday uniform + vintage shopping in Berlin and a sweet '80s Kenzo find
As a self-identified Carry-On Princess, I do my best outfit repeating while on vacation.
Last time we spoke I was munching on bear-shaped potato chips writing from an Airbnb in Prenzlauer Berg. Today I come to you from sunny Sydney, Australia, where my vacation uniform involves less wool and much more sunscreen.
Given the length of this trip and the midway climate shift — drizzly German autumn to an unseasonably warm Sydney spring — the space in my suitcase was extra precious. It was the perfect excuse to pull out all my best tips on travel dressing and share the packing rule I live by: You only really need one great outfit on vacation.
In this letter:
Why I love to wear the same outfit every day on holiday
How I built my perfect Berlin uniform
Misc notes on Berlin style + the one vintage piece I bought on the trip
It’s an incredibly practical way to pack.
I despise checking a bag. I’m convinced mine is the most likely to be lost, and given that I shop almost exclusively secondhand and vintage, so much of my wardrobe is tough to replace. Packing a few items that all work well together means I can Tetris my carry-on to perfection and still have a bit of space for souvenirs.
In Berlin I rotated through a variation of the same base outfit built from 10 pieces. Six out of 10 of those pieces were on my body while I flew, so I only required a small section of carry-on for those remaining four to complete a full vacation wardrobe.
It relieves unnecessary stress.
There are few things I love thinking about more than clothes. But on vacation, I prefer to spend my time thinking about the travel — the food, the culture, the flora and fauna, etc. My daily life at home feels lifted by endless fashion choices, but while traveling, it can sometimes feel like more of a burden trying to nail down the “perfect” look each day.
Vacation dressing is joyously low-stakes.
And in the same vein, the likelihood of running into someone whose opinion you should care about is at an all-time low. You don’t know anyone, they don’t know you, and no one will track the number of times you step out in the same t-shirt or pants.
Kendall Flavin and I discussed this in detail here, the idea that dressing on holiday can be the perfect time to experiment precisely because no one there knows you. Vacation you can take as many styling risks as they please, and they can wear the same outfit every day with no judgment if they please too.
It’s whimsical, no?
Remember that TikTok trend where people were showing off what a cartoon character of them would where every day? That’s how I feel in my little vacation outfit. While I’m packing I think to myself, “how would cartoon Mac dress in this city?”
Step 1
I knew I needed a warm coat. Something that was comfortable over a sweater or a t-shirt and relatively rain resistant. I landed on a vintage ‘60s wool varsity jacket in a bright kelly green with red leather trim. Given the weather, I knew this coat would be the focal point of the outfit and chose the rest of the pieces around it. I threw in a warm cardigan and a fleece vest in case of a layering emergency.
Step 2
Comfortable pants! Something wider leg is best for warmth and darker colors felt more ‘autumn in Germany’ to me, so I landed on indigo jeans and black cotton trousers. The first pair is low- to mid-rise, the latter is high-rise, and both are forgiving in the waist regardless of how much schnitzel I’ve had at dinner or how upset my stomach is at the travel. Flexibility is key with a limited wardrobe.
Step 3
Simple tops to rotate through. It was freeing to know my top was nearly always going to be hidden under the coat and/or a sweater layer — no need to worry too much about what was going on under there. I opted for comfortable cotton t-shirts that wouldn’t need to be washed every day: two in neutral tones and a third with a striped pattern that matched the green + red + blue color story I had going on (my very favorite color combo).
Step 4
Shoes that survive 15k+ days. I knew I’d be clocking thousands of steps in wet weather, so I went with trusty Blundstone boots that are easy to throw on and great for rainy days.
Step 5
A bag to carry all and withstand all. My favorite travel-friendly bag is a Baggu nylon medium crescent (a shocking revelation, I know). I call this bag the fuel-efficient mid-sized SUV of purses because it’s just so damn practical. I brought a black version from the Molly Goddard collab which has an adjustable snappy strap.
This prep landed me with the following ingredients:
Still Here Walker Jeans in Indigo
Wilfred Free Cotton Trousers in Black (secondhand options here)
Negative Whipped Long Sleeve in Heather Grey1
Rolla’s Striped Ringer Tee (not sold anymore but I love this Sezane one)
Vintage ‘60s Wool Varsity Jacket
Vintage ‘90s Mountain Hardwear Fleece Vest
And I cooked it all up into this.
The only pieces that deviate here are the red Longchamp tote (my personal item on the plane which I stuff the Baggu into) and denim shorts that I had to break out on a random 80+ degree Sunday as I ran around the city trying to catch my friends running the marathon. Lucky I was headed somewhere sunny next so I had them packed!
Two sides of Berlin style. People watching in Berlin was so fun. I noted a delicious excess of chunky silver jewelry, cropped funky haircuts that felt incredibly fresh, some sick vintage Adidas track jackets, and, of course, plenty of good ol’ Birkenstocks. Even in the rain.
not pictured: plaid shirt’s mustache and book lover’s eyebrow piercing and pixie cut I might forever regret not buying this teal suede tie. I was out of cash and out of time to go get more cash, so I walked away as fast as I could just to rip off the band-aid. Miss her :/
My single sartorial purchase in Germany was this vintage ‘80s Kenzo fruit top I found tucked away on sale for €25. Bless all those who didn’t give it a chance before me because it fits like a glove and is in perfect condition.
Berlin vintage shops are crawling with Custo Barcelona and Save the Queen, two iconic European maximalist brands that feel harder to find in the U.S. The selection of curated vintage shops in Kreuzberg is so good — my friends and I specifically loved Spatz Vintage, Not Too Sweet, and Sing Blackbird, where E bought not one but two perfect black jackets.
Not Berlin-related but certainly just as fun… Viv Chen snagged this stunning vintage Miss Sixty fringe belt from my fall wishlist letter and I could not be happier that it went to such a loving home. So good how the piece shines against a simple white dress. Yay Viv!
I’d love to hear how you plan your outfits for travel — even more so if you’re my polar opposite who loves to check six bags. How fun that we all make style decisions so differently?
Find me on Insta here, send me a note at mackinley@yeehawt.com, or reply to this email to keep the convo going <3
In case you missed it:
Got boots on the mind (what’s new).
Wearing this cardigan while writing rn. Soooo cozy.
Negative also makes the best bra of all time. I get this question a lot and this is my eternal answer — 99 out of 100 days I’m wearing one of their whipped fabric bralettes.
I love this! I’m also a carryon-only queen (nonrev necessity!) but I tend to squeeze as much as I can into every cranny, though I’m thinking of trying the cartoon character method next trip (scotland in nov). I take more pics of myself/outfits while traveling so I want to have variety! I’m also a blundstones & baggu travel girlie, they’re just so easy & practical.
This is just the post I needed to see before packing for 10 days in Italy! I’m trying to only pack a backpack + personal item for this trip, and I love how you chose the focal point of the vintage jacket to have your other items kind of swirl around. It’s a very chic take, and I think you should share this very article on Reddit.com/r/HerOneBag. They would love you there!