I Spent Over 150 Hours Traveling Last Year—5 Outfits Always in My Carry-On

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(Image credit: @trustmebuythis)

I've always joked that I would live my life out of a suitcase if I could. Although that's theoretically impossible with the state of my closet, I'm as close as I'll ever get. After 24 years of long-haul trips and more airline miles than a Victorian-era child could ever imagine, I've perfected the art of packing thanks to smart, thoughtful outfit choices that will last me a week and a half that fit in just a carry-on suitcase.

Since worldwide shutdowns nearly two years ago, 2022 was a return to traveling for me. In total, I racked up over 150 hours on the go, including heading to Japan to see family, meeting up with friends in Spain, and taking road trips throughout California and New York. If I hadn't had packing down to a science at this point, I don't know how I would have done it. 

With the amount of airline rerouting and luggage delays nowadays, no one needs infinitely more stress when it comes to packing for a weekend trip if your luggage gets lost. Although it hasn't happened to me yet (fingers crossed!), the number of horror stories I've seen on social media has made me begin to pack a few days' worth of clothing I carry with me at all times. 

Below are the foolproof outfits I pack each time I escape the city and travel somewhere new. 

Black Trousers + White T-Shirt + Colored Cardigan 

Call it classic, or call it the Matilda Djerf effect, but ever since replacing my airport-approved sweats with comfortable pants and basic tees, I've felt much cooler. For nearly every fashion capital you're in, this timeless combo never goes wrong. For the adventurer, a brightly colored knit cardigan or sweater is always key for traveling to colder climates (or freezing airport lounges).

Fitted Jeans + Striped Shirt + Denim Jacket

Denim on denim is set to be one of the smartest purchases of 2023, so naturally, the Canadian tuxedo has made an appearance in my travel bag. Breton stripes aren't just for French girls and tourists, though—the classic combo can be worn with nearly every type of bottom and still look put-together. 

Two-Piece Set + Elevated Crossbody Bag

As much as I admire aviation outfits from the '60s and '70s, there's no way I can constantly wear heels and hosiery on a six-hour fight. If you feel like dolling yourself up like how people did back in the day to head to the airport, look no further than a Pinterest-approved two-piece set.

Little Black Dress + Statement Evening Bag

There's nothing quite like discovering a chic, swanky bar while on vacation. If you're anything like me and live in comfortable clothes 24/7, the opportunity to head out for a night on the town in a new city calls for the best eveningwear. No matter the location, weather, or current trend cycle, an LBD and statement purse never go out of style.

Fleece Sweater + Long Socks + Beanie + Leggings

In 2023, jet lag is my personal public enemy number one. While combatting different time zones and still remaining cute, I've turned to fully embracing the sloth vibe: leggings, socks, and a cozy beanie paired with ultra-luxe fleece. Thankfully, basics from brands like ALO and ASOS are lifesavers tucked into my carry-on in the off chance that my luggage doesn't arrive.

More Airport Essentials to Shop

Next, The Coolest Ways to Wear Leggings to the Airport

Assistant Shopping Editor
Ana Escalante is an award-winning journalist and Gen Z editor whose work ranges from dissecting size inclusivity at fashion week to discussing how American Girl Doll meme accounts are the the answer to society's collective spiral. She's covered it all: Queen Elizabeth II's corgis, Roe v. Wade frontline protests, and the emergence of jorts (or jean shorts for the uninitated). At Who What Wear, Ana is responsible for delivering smart, insightful, personality-driven shopping guides and trend features for a digital-first generation.

Before joining Who What Wear, Ana was Glamour magazine's editorial assistant, where she focused on daily news and special packages, including leading the brand's 2022 Met Gala coverage. For more than half a decade, she has covered style, beauty, and digital culture for publications such as Paper magazine, Harper's Bazaar, Vogue Japan, and Allure, among others. Ana has been called a rising star in media by publications such as Nylon and Teen Vogue. (Her mother, meanwhile, calls her "the coolest person" she knows.)