How to Do Holiday Travel Style Like a Fashion Editor

what to wear on a road trip


Collage Vintage

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

Graphic sweatshirts are perfect under a denim jacket.

Available in sizes XXS to L.

You will never want to take these leggings off.

Available in sizes XS to XL.

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

Wear your oversize sweater with a black suede miniskirt.

Available in sizes 1 to 3.

Never leave the house without this coat.

Available in sizes XS to L.

Dark-wash denim is a wardrobe necessity.

Available in sizes 23 to 32.

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

Show off the rainbow detail by wearing light-wash denim and a white tee.

Available in sizes 7 to 13.

The ultimate cool staple.

Available in sizes XS to XXL.

Leather jackets are the best day-to-night style.

Available in sizes XS to XL.

Pair with simple sneakers.

Available in sizes S to XXL.

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

Similar style seen on Bella and Gigi Hadid.

Available in sizes XS to L.

Wear a plaid blazer over yours.

Available in sizes XS to XL.

“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

Keep your outfit simple with this color blocked sweatshirt.

Available in sizes XS to XL.

The perfect high-rise leggings.

Available in sizes 2 to 12.

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

Customizable clothing? Yes please!

Available in sizes 00 to 14.

Vintage denim and black boots is our go-to outfit.

Available in sizes 23 to 32.

Wear with sneakers or ankle boots to show off these cool socks.

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

Stay warm during the colder months with this long jacket.

Available in sizes XXS to XL.

Show off your shoes with these cropped jeans.

Available in sizes 24 to 32.

Wear your hair up to draw attention to the shoulder detail.

Available in sizes XS to 4X.

“A road trip is all about comfort, so now’s the perfect time to break out your coolest sneakers and coziest sweater. I love how these wide-leg pants add a cool tomboy spin to the look.” — Anna LaPlaca

Style yours with cropped black denim.

Available in sizes 1 to 3.

Fashion girls love high-waist wide-leg trousers.

Available in sizes XS to L.

Comfortable and stylish.

Available in sizes 6 to 8.

Next, read about the minimalistic wardrobe staples you haven’t tried yet.

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