The Best Travel Outfits for More Comfortable Trips

Sometimes the puzzling part of travel isn’t the planning and reservations, but finding clothes to wear in transit that’ll be comfy enough yet also let you emerge from the plane (or car or train) stylish and unrumpled. 

That balance can be difficult to achieve, and the challenges of modern travel had led many people to lean more into pajamas and less into pant suits. After years of working in travel journalism, I’ve found there are suitable outfit upgrades. Brandon Berkson, a frequent traveler and founder of Hotels Above Par based in New York City, also weighed in with tips about what makes a great travel outfit, and the best pieces to add to your wardrobe before your next trip. 

Stealthily comfortable

Jeans with plenty of stretch, like this Bonobos pair that’s specifically designed with travel in mind from Bonobos or this pull-on Spanx option are solid choices for those who want to avoid sweats. Add on a cardigan sweater, like these men’s and women’s styles from Quince, made from breathable cashmere or wool to complete the look. “Cardigans are a great way to balance comfort and a put-together appearance,” Berkson says—his favorite is this “smart-casual-while-snug” wool style from Comme des Garçons. Or, take the hidden comfort angle a bit further with these Rag & Bone sweatpants that mimic the look of actual denim surprisingly well, but are made from soft cotton terry. 

Athletic look

These athletic-leaning pullovers and hoodies from Vuori will look more polished than your average sweats. Complete the look with the Sunday Performance joggers in men’s and women’s styles. The stretchy, moisture-wicking fabric is designed to keep its shape and stay dry through long flights, even when temperatures fluctuate.

Modern silhouette 

For those who want the ease of athleisure with a luxurious look, opt for these matching separates from Spanx. It offers a modern silhouette with flared pants and a half-zip top for a versatile look you can take from the airport to a day of sightseeing. The blend of modal, polyester and elastane is lightweight and non-restrictive, so you can layer with ease without fear of overheating. 

Head-to-toe cashmere

Since airplanes are historically chilly, matching cashmere sweaters and joggers will come in handy any time of year, though they’re a particularly smart option in the wintertime when you’re aiming to pack light. My machine-washable Naadam crewneck (it also comes in men’s sizing) is my go-to layering piece for flights and once I land because of how soft and breathable it is. Mix and match to find your preferred top and bottoms in a color you’ll incorporate into the rest of your travel wardrobe. 

Adventure travel style

Versatility is a virtue when it comes to a travel outfit. That’s why we turn to REI for its convertible separates. These pieces, including a pair of quick-drying nylon and spandex cargo pants (also available in women’s sizing) that zip off at the knee and an airy button-up shirt with adjustable sleeves (in men’s and women’s sizing), will take you through busy airports, stuffy cab rides and frigid airplanes with ease, but they’ll also come in handy on that hike once you reach your destination.

Cold-weather friendly

For ski trips and other cold-weather locales, having good base layers is key. Ibex’s lightweight yet ultra-warm layers are a winner, as are the brand’s sleek active separates, including moisture-wicking cotton terry joggers for men and women and merino wool jackets, like this sporty bomber and classic zip-up, which can transition from the plane to the slopes in a flash.

Must-have accessories

Berkson suggests carrying a small crossbody bag on flights, like this Rains pack, which helps him avoid fumbling through his pockets for his phone, passport and printed boarding pass. “With this strapped across my torso during a long day of globetrotting, I don’t misplace my belongings anymore when en route to a destination,” Berkson says, “nor do I have to worry about them accidentally falling out of my pockets.” 

Socks are also key; this compression pair comes recommended by Alexandra Stockton, a Knoxville, Tenn.-based travel advisor, who says she wears them to prevent aching and swollen legs. Berkson praises this Todd Snyder pair for being “exceedingly comfortable.” The cotton-blend should keep your feet warm without overheating, even if you’re heading to a warmer locale.