13 Comfy Travel Outfits (That Are Definitely Not Pajamas)
I get the allure of celebrity airport fashion. There's something romantic about emerging from the skybridge in an outfit worthy of Beyoncé, Michelle Obama, or the reigning queen of traveling in style, Victoria Beckham.
But we mere mortals are — quite literally — not on the same plane.
We do not need to prepare for an assemblage of paparazzi waiting to shoot up at us from the tarmac. We just need to sit in one place for an extended period of time without experiencing incredible discomfort due to our clothing choices. Here’s how.
First, to prepare for the temperature roulette that is inherent in travel, you’ll need layers. To be a practical packer, you’ll need versatile pieces that you can reuse throughout your trip. And to be not miserable, please pack clothing and shoes you’ve already road-tested and know to be comfortable for your body and your being.
Taking notes from the travel style of not just off-duty models, celebrities, and royalty, but also bloggers, social media stars, and normal, real-life people just trying to survive JFK-HAN, I realized there kind of is a general consensus.
The perfect travel outfit is actually super formulaic. You need five things:
- A T-shirt — one that’s soft, well-made, and loose fitting
- A Jacket or Cardigan — something neutral and warm
- Fitted Pants with Stretch — look for elastane-blend stretch-denim, or tailored joggers
- Comfortable, Stylish Shoes — smart sneakers, flats, or a low heel
- One Signature Accessory — a little something extra to make it feel more “you”
Before you write that off and just toss on whatever, hear me out. Of course, you won’t remember what you wore on any given trip, but the comfort and confidence that come from the perfect travel outfit are meaningful. Your style can change your approach to what you do and who you are abroad.
Here, 13 outfits to make you feel like less of a tourist and more of a traveler.
Something as simple as buckle detailing at the ankle can turn lazy sweatpants into on-trend joggers ($30; zara.com). Add a super-soft Splendid cotton and modal–blend T-shirt ($55; net-a-porter.com), an athletic jacket like this one from Riccardo Tisci’s Nike collaboration ($245; farfetch.com), and one of our favorite pairs of walking shoes, Asics’ Metrolyte sneakers ($65; zappos.com) for an outfit that won’t get in the way when you’re trying to get comfortable. Pro tip: the twisted head wrap ($4; forever21.com) doubles as a decent makeshift eye mask.
Frequent Flier Attire
Frame’s Le Skinny de Jeanne jeans ($209; matchesfashion.com) are made of cotton-blend denim with just the right amount of stretch and designed to stop right at the ankle, perfect for showing off some boldly printed skimmer flats ($220; nordstrom.com). Top them off with a muted, striped T-shirt ($145; matchesfashion.com), a lightweight anorak ($70; hm.com), and a patterned silk scarf ($185; nordstrom.com) for a look that’ll rack up tons of mileage points.
There’s no better way to upgrade a T-shirt ($19; joefresh.com) and sweats ($425; net-a-porter.com)—wool and cashmere–blend sweats, might I add—than a leather moto jacket ($550; jcrew.com) and Chloe’s signature gold-tone studded slip-ons ($695; mytheresa.com). And don’t forget your personal item: a delicately modern monogram necklace ($360; neimanmarcus.com).
Don’t Say Bomber
Good luck getting through security without being asked where you got this gorgeous, embroidered bomber ($120; mango.com). Style it with a silk camisole ($158; tibi.com), a goes-with-everything crystal collar by Dannijo ($420; saksfifthavenue.com), leather ankle boots ($140; zappos.com), and a pair of jeggings ($55; ae.com) so snug and stretchy you’ll forget the word “jegging” is also unspeakable.
Channel the model off-duty vibe with stretch-scuba leggings ($450; matchesfashion.com), a long T-shirt ($15; aritzia.com), an unfussy woven jacket ($50; hm.com), and an Apple Watch Sport ($375; amazon.com). And be prepared for the race between terminals with these cool canvas sneakers ($65; zappos.com).
Everlane’s Modern Oxford ($175; everlane.com) is my new favorite pick for a one-shoe trip. The style is so smart and versatile that it’s worth spending 24 seconds to untie them for the TSA. Pair them with white stretch-denim jeans ($190; matchesfashion.com), a loose, wool-blend camisole ($129; matchesfashion.com), a cozy, duster cardigan ($432, matchesfashion.com), and an everyday watch ($105; amazon.com) to match.
Mix prints with a striped T-shirt ($13; zara.com) and a floral, satin pilot jacket ($40; hm.com). Add a little more fun with knotted tassel earrings ($45; revolve.com). And balance it out on the bottom with high-rise skinny jeans ($135; madewell.com) and low-top leather Common Projects ($410; matchesfashion.com).
Keep comfort classy with a sleeveless turtleneck ($13; hm.com), relaxed-fit, printed pants ($160; net-a-porter.com), and a camel wrap coat ($60; hm.com). Add sleek loafers ($68; nordstrom.com) and a statement necklace like this Alexis Bittar pendant ($195; alexisbittar.com) that’s pretty much a piece of art, and you’re (jet) set.
This luxe merino wool cardigan ($289; stylebop.com) is soft in both texture and color, a perfect fit with a twist-front crop top ($28; topshop.com), high-waisted, relaxed-fit trousers ($80; topshop.com), and Repetto’s ultra comfortable ballet flats ($295; zappos.com). Don’t forget a pair of retro Gucci sunglasses ($470; nordstrom.com) for some chic above-cloud window watching.
For a timeless base look, tuck a striped jersey top ($40; net-a-porter.com) into high-rise skinny jeans ($128; madewell.com). Add a pleated neck-tie scarf ($28; freepeople.com), sleeveless, long-line cardigan ($130; farfetch.com), and platform oxfords ($120; nordstrom.com) and you’ll be street-ready seconds after checking in.
Plane & Simple
For streamlined style, stick to the basics: a light graphic T-shirt ($26; mango.com), cuffed boyfriend jeans ($184; matchesfashion.com), and an iconic trench ($298; jcrew.com). A checked blanket scarf ($26; zara.com) will come in handy when the cabin gets cool, and an elastic band hidden under the tongue makes these cap-toe loafers ($175; nordstrom.com) easy to slip on and off.
These super-soft J Brand stretch-denim jeans ($185; net-a-porter.com) are as every bit as curve complimenting as they are comfortable. With New Balance 620’s ($80; jcrew.com), some charming drop earrings ($36; baublebar.com), a split-back, stretch-cotton shirt ($270; net-a-porter.com) and a toasty, boiled wool sweater ($178; madewell.com), you can spend a few in-between hours exploring whether your stopover’s in Sacramento or Reykjavik.
The rose-gold tones of these Adidas by Stella McCartney sneakers ($230, saksfifthavenue.com) and jacket ($182; farfetch.com) give upscale athletic vibes to a heather grey, cap-sleeve T-shirt ($35; gap.com) and Athleta’s stretch cotton skinny cargo pants ($89; athleta.com). Meet the sunny skies of your destination with Ray-Ban’s folding Wayfarers ($155; bloomingdales.com).