We all love to be as comfy as possible when we travel, but I’ve never been one to board a plane in pajama pants. For one thing, it’s fun to offer a small sartorial nod at the fact that decades ago, taking a plane or train on a long journey was a dressy affair. More selfishly, though, I like to be as ready as possible for a day out on the town as soon as I arrive at my destination.

When you’re not able to check into a hotel to change right away, have a big event planned as soon as you land, or simply want to squeeze in as much time sightseeing as you can on a short trip, the key is to dress in versatile basics that keep you cozy enough to take a nap en route but stylish enough to get through the rest of your day with nothing more than a quick shoe change.

Whether you’re looking to go casual or have something a bit dressier in mind, find some inspiration in the travel style looks below!

1For The Sunny Day-Tripper


This dress is long and soft enough to kick back on the plane, yet enough of a vacation staple to look great wherever you’re going. If you’re looking for a little more oomph, slip into some playful heels when you arrive.

//French Connection Striped Sheath Dress, $39.99; Kate Spade Leather Backpack, $348; M. Gemi Saltare Flats, $198; Muubaa Leather Jacket, $312.50; Fresh Sugar Lip Treatment, $22.50; Lulu’s Ankle Strap Heels, $34

2For The Casual Free Spirit

For those forever in pursuit of mastering the perfect balance between full-on athleisure and “this is totally work-appropriate, I swear,” try some dolled-up leggings that bring something extra to your look but still leave you totally prepared to sit cross-legged in your plane seat.

//Helmut Lang Zip-Up Sweatshirt, $230; Karen Walker Sunglasses, $280; Anthropologie Fluttered Peasant Tunic, $39.95; Nine Speakup Ballet Flat, $69; Sonoma Crossbody Bag, $34.99; Charles by Charles David Wedges, $40.79; Fabletics Gardenia Crop Leggings, $54.95

3For The Power Woman About Town

Capes are essentially socially acceptable blankets, yet they manage to make an outfit look more put-together than just about anything else. Drape yourself in one for your long commute, then trade the wool for some bright stilettos for an evening out in your new destination.

//J.Crew Cape Jacket, $250; Dolce Vita Slip-On Loafers, $50; DKNY Silk Blouse, $255; J.Crew Pixie Pant, $98; Pan Am Explorer Bag, $89; Kate Spade Licorice Pumps, $229.60