13 Comfy Travel Outfits (That Are Definitely Not Pajamas)

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.

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).

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.

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).