Truth be told, holiday style can sometimes throw us for a loop, especially when it comes to what to wear on a road trip. Should you go casual and comfortable with an outfit that will have you dozing off to your Spotify list or snuggled up into a new book? Or is it better to opt for something cool and stylish? One never knows when a pit stop will present an interesting photo op, after all. To get some insight, I tapped my fellow Who What Wear editors—after all, they’re experts when it comes to all things style. Ahead, they’re sharing the pieces they’ll be wearing this season for their holiday travel looks and offering tips to help you pick out an outfit you’ll love.
Go on to find out the outfits they’ll be wearing this holiday season.
“My family road trips involve lots of hiking, so my go-to holiday look skews practical (but is still cute).” —Aemilia Madden
Seen on the streets of New York and Paris fashion weeks.
Available in sizes 6 to 10.
“I always wear slim stretchy jeans when go on a holiday road trip, along with a cozy sweater or soft T-shirt (depending on the weather), and a pair of shoes that I can easily slip on and off.” — Allyson Payer
Dress your outfit up by wearing leather leggings with these mules.
Available in sizes 5 to 11.
“I tend to stick to my normal uniform when I’m on a road trip—just slightly more relaxed. Typically that consists of a cozy sweatshirt or sweater, joggers, sneakers, and a jacket I can take on and off.” — Bobby Schuessler
Use this to carry all your favorites for a weekend trip.
“I keep it super comfortable when it comes to dressing for a road trip. I typically go for a pair of stylish sweatpants like the ones below (the material is crazy soft) and an oversize T-shirt.” — Michelle Scanga
“I want to be as comfortable as possible on a road trip and be ready for exploring different stops, so leggings are perfect—and they can still look stylish with a graphic hoodie and cool sneakers.” — Erin Fitzpatrick
These soft lightweight shoes will be your new favorites.
Available in sizes 5 to 10.
“I recently custom-designed this coat (welcome to the world of Frilly, if you haven't experienced it yet) and plan on wearing it everywhere this season. Paired with casual denim and low-heel ankle boots, this look could not be any easier. Since we are talking about road trips here, I’ll definitely be sporting a cool pair of socks to snuggle up in in the car once I take my pointy boots off.” — Lauren Eggertsen
White ankle boots are one of this season’s biggest trends.
Available in sizes 6 to 10.
“When it comes to travel outfits, I think the most important thing is comfort and then, of course, looking cute. Over the years, I’ve perfected a combo that checks both boxes and can be re-created a million ways. It’s a cozy coat, a stylish sweater, stretchy jeans, and sneakers. Works every time.” — Nicole Akhtarzad