We're Fashion Editors and Frequent Flyers—8 Outfits We Swear By to Look Cool (and Be Comfortable)

As fashion editors who travel the globe like it's our job (it often is), we're pretty particular about what we wear to the airport. If not for a vacation or personal trip, our team of editors can often be found traveling for an international fashion week, destination runway show, or brand trip. This year alone, our reporting has taken us all across the globe from Seoul to Marrakech and back again. While traveling that far isn't necessarily a regular occurrence, we do find ourselves zipping up our suitcases often enough to have formed strong opinions on what to wear—and not to wear—to the airport. Comfort and practicality is always key, but each of us has unlocked our very own outfit combinations that are as stylish as any TSA line can get.

Whether they're hopping on a four- or 14-hour flight, I tasked each of our editors to share an example of their perfect travel outfit, the trip they wore it on, and the details that make it a 10/10. From the trompe l'oeil sweatpants that look deceivingly like jeans to a tote bag that can fit almost as much as a carry-on suitcase, see how our team has perfected the art of the elusive cool-yet-comfortable travel look.

WHO: Bobby Schuessler, Market Director

WHERE: Madison, Wisconsin to Los Angeles, California

"I know some people have very strong reactions to the whole 'wearing jeans on a plane' thing, but unless I'm traveling internationally, I always wear jeans—I just focus on comfortable, relaxed cuts. To keep my ensembles polished, I typically opt for some sort of jacket, blazer, or sweater over a T-shirt. It's all about layers because the temperature can change so drastically on flights. This specific look is a great sample of what I typically wear with the loose jeans, oversize blazer, and sneakers."

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WHO: Kristen Nichols, Associate Director of Special Projects

WHERE: New York, New York to Nantucket, Massachusetts

"For long-haul flights, I usually opt for relaxed trousers or drawstring pants with a T-shirt and crewneck knit for an easy look that feels polished yet comfortable enough to endure a red-eye. For quicker trips, I typically wear a button-down shirt and lived-in vintage jeans and some sort of flat shoe like a soft leather loafer. I love to arrive in something I can wear straight to a low-key dinner."

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WHO: Anna LaPlaca

WHERE: New York, New York to Geneva, Switzerland

There's only one outfit combination I'll wear when my flight time is longer than four hours, and I repeat a variation of it every time I travel internationally. It all starts with a pair of soft pants that feel like sweats but look far more elevated—my two favorites right now are the Éterne Brody Pants, a luxe silk drawstring pair, and the Donni Rib Kick-Flare Pants, which are made from the most buttery-soft knit fabric. Then, I'll wear a shrunken T-shirt and a sweater over it that I can also wear over my shoulders if I need to. Even though sneakers are the most obvious choice for travel days, I actually prefer ballet flats, as I've found they're no less comfortable but make me look and feel much more put-together.

As far as carry-ons go, I'm very passionate about my Lululemon tote. The details are just so functional that it makes or breaks my whole travel experience if I bring it along. It features a panel that hooks over the handle of my roller board; a mini zip pocket for easy access to my phone, ID, and passport; and internal slots for a laptop, charger, and extra pair of shoes. It's light as air but fits so much.

WHO: Sierra Mayhew, Fashion Editor

WHERE: London, England to Barcelona, Spain

"For a long travel day, I always build my outfit around my sweatpant jeans—especially this pair from Rag & Bone that I never stop talking about. They look like real denim but feel like pajamas, which is basically the dream scenario for a flight. I’ll usually pair that with a white tank or tee and layer on a sweater over my shoulders so it’s easy to carry and ready to pull on when the plane inevitably gets freezing. My shoes depend on the season but most often I end up in my bulkiest boots to save space in my suitcase. The one thing I’ll never understand? Wearing heels to the airport—I’ve tried it, and it inevitably will slow you down."

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WHO: Allyson Payer, Senior Editor

WHERE: Raleigh, North Carolina to Los Angeles, California

"My go-to travel outfit is pretty much always the same, no matter the time of year. It always consists of a boxy T-shirt and jeans with some stretch in them—usually Agolde since its jeans never look like they have stretch in them. A jacket or lightweight sweater of sorts is a necessity, as I inevitably go back and forth between hot and cold throughout a long travel day. And last but not least, always a baseball cap and cute flats or sneakers. (These days it's the Dries Van Noten ones for me, which I somehow acquired in four colors.) I don't wear much jewelry on travel days but always put on a pair of simple hoop earrings before I walk out the door."

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WHO: Eliza Huber, Senior Fashion Editor

WHERE: New York, New York to Seoul, South Korea

"I have now traveled to/from Milan, Seoul, Miami, and Chicago in this exact outfit (with just a few shoe changes). It's made up of my biggest piece of outerwear that I'm bringing, which on all four trips has been a chocolate-brown Fforme car coat that can be dressed up and down and doesn't ever wrinkle, two traits I look for when I'm traveling; an oversize white T-shirt, either from Agolde, Madewell, or Citizens of Humanity; black Veynd yoga pants; and whatever sneakers I plan to work out in while I'm traveling. Mostly, I've brought my Salomon Whispers, but on my last trip, I wore Puma's new H Street sneakers (definitely not for running, but they worked fine for lifting). My bag situation changes every time, but my Longchamp expandable Le Pliage bag has never done me wrong, and I always travel with one of my Tumi aluminum suitcases—I have the international carry-on, extended trim packing case, and trunk."

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WHO: Judith Jones, Associate Shopping Director

WHERE: Los Angeles, California to Riviera Maya, Mexico

"When I travel, I always opt for comfortable pieces that feel elevated and effortless. These stripe drawstring cotton pants are the next best thing to wearing pj's, yet they feel trend-forward. I pair them with a quality black crewneck T-shirt. (Norwegian designer Julie Josephine is my go-to for chic, soft, and comfortable T-shirts.) I'll almost always wear black in case of spills, for hiding sweat marks, etc. And I'll finish the look with comfy retro sneakers. Gola's black and white styles are versatile and cool."

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WHO: Tara Gonzalez, Senior Fashion and Social Editor

WHERE: New York, New York to Marrakech, Morocco

"The perfect travel outfit has always eluded me. I am an overdresser to my core; I have trouble doing something casual. When I'm at the airport I still want to look like myself but also be practical and comfortable enough to spend hours in the air. For years, I looked ridiculous. I couldn't figure out a 'fit that made me look both cute and casual. Finally, this year, I found this Sandy Liang rosette sweatshirt set. It perfectly encapsulates my style—it's a little silly and unserious while also being a bit masculine and girly. It's the perfect mix of every vibe I like. It is also the most comfortable thing I own. I can easily fall asleep on the plane in it, but when I wake up, I'm eager to snap a selfie in it. It makes me feel that good!

"I've been pairing it with an easy black Hanro tank top and white Salomon sneakers, which are both good things to have on hand for my trip that I don't have to pack. Not to mention the sweatpants and sweatshirt are cozy layering pieces I often incorporate into more easy looks throughout my trip. Seriously, this is the most versatile airport outfit I've ever worn, and I love it more with every trip I take in it."

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