The 8 Best Travel Dresses of 2020

Eileen Fisher is known for creating comfortable, chic dresses that drape and flow, and her drop-shoulder tee dress is emblematic of her minimalist style. We love all the functionality this dress brings to the table: a high-low hem for a little extra length, a pullover fit that makes slipping in and out of it easy, and yes, it has pockets, too. This is a feel-good purchase, as well; the dress is eco-consciously constructed, made from 90 percent organic cotton and 10 percent spandex for a breathable, stretchy-but-not-too-stretchy fit that moves. The t-shirt dress is designed to be a little oversized, so order a size down if you’d like a closer fit. In colder months, pair it with a leather jacket or tights and booties; come summertime, sandals will do you just fine.

If you want something as down-to-basics as it gets, this loose t-shirt dress is a great go-to — and at less than $30, it’s not going to break your vacation budget. With more than 20 colors to choose from — hunter green, dark rust, mustard, and black included, there’s a hue (or two) suited to every traveler out there. We like that the sleeves, hem, and cut of the dress are long and loose enough that it works well — sartorially speaking — in more conservative destinations. Most importantly, it’s incredibly comfortable and it even has pockets. Rounding out your outfit won't take much, either; throw on some jewelry for drinks out or keep it simple by using it as a coverup when you're coming from or heading to the beach.  

Nothing marries comfort and style quite like a wrap dress, and this option from Toad & Co hits the nail on the head. The above-the-knee length isn’t too short for moving around comfortably, and it’s not so long that it’ll look awkward with leggings or tights. The tie hits slightly above the waist in an empire cut, which makes for more comfortable bouts of sitting, and the A-line cut is flattering on pretty much every silhouette. The dress is available in a variety of vivid colors and prints, from a red-orange to turquoise — and best of all, they’re all smart enough that you could wear it straight from your plane to a meeting. Bonus: the dress is made from soft Tencel and organic cotton, making it an eco-friendly pick.

This versatile dress is excellent for fall and winter travel. Hailing from Max Mara’s Weekend line — which flawlessly executes relaxed but elevated pieces — the design features a midi-length chiffon skirt with a sweater top so can pack a one-piece that does the work of two closet staples. The sweater hits just above the waist in a cropped fit, with a round neck and long raglan sleeves so you can stay cozy mid-flight, while the pleated skirt is chic without sacrificing comfort or casualness. Listen — we know the dress is quite a splurge, but it can truly take you from museums and attractions (try pairing it with some sporty white sneakers) to high-end dining and nights out (throw on some booties or heels). The dress fits true to size, so order your regular size and you should be good to go.

This dress from the Nevereven combines a modern cut with great detailing. Made from viscose, a blend of cotton and rayon that’s exceptionally breathable, the dress is an easy, breezy choice for stressful travel days. If you’re a cold flyer, throw some tights on underneath with a pair of suede booties for a boho-chic look that keeps you comfortable. Or, keep it cool with slip-on sneakers or sandals and a few layered necklaces for an island-ready outfit that gets you in the mood for vacation the second the Uber pulls up outside your door.

The best travel dresses are ready to take on a number of activities, and this dress from Revolve is capable of moving from sightseeing to the beach, to drinks, and back. Despite an initially sunny outlook, the dress is more versatile than it appears. It’s fully lined, so you’ll always have an extra layer between you and any unexpected chilly temps. Plus, it pairs just as well with a long cardigan as a sharp cropped jacket for cooler days. The same can be said of footwear options: the Laura dress looks just as cute with a pair of suede booties as it does with boardwalk-ready beaded sandals. The fit, with a smocked waist and long skirt, is flattering without being too tight, and it offers a nice shape that departs from popular oversized looks. The balloon sleeves are a nice on-trend touch, too, and the metallic fibers woven throughout mean you can easily head off to happy hour without changing.

It’s hard to go wrong with denim: It’s a durable, versatile material that’s easy to clean and can hold up to the stresses of travel. The Mo Dress is comfortable for a day spent traveling, too, thanks to a zip front, empire waist, smocked back, and midi-length skirt that works in most weather. Plus, two deep pockets on the front hold everything from phones and earbuds to passports and boarding passes. You can easily layer it for a flight, too, whether you opt for a black turtleneck underneath or a cardigan over the top. It does run a little large, so size down to avoid the hassle of returns and exchanges.

If you want all the comfort of an oversized sweatshirt but a more polished aesthetic, this velvet dress by Michael Stars is just the thing. The mini-length design is great for all seasons; pair it with strappy sandals, tights and leather booties, or thigh-high boots depending on the weather. The glam dress suits a number of itinerary stops — from cocktail hours and dinners to shows and other nighttime events. It fits true to size, though there is a generous swing to it if you’re between sizes and want to go down one.