40 Fall Dresses for Travelers, From $14

When it comes to fall fashion, comfort reigns supreme. Cashmere blends, soft cotton, and loose-fitting fleece and flannel make their way from the back of closets to replace our breezy summer faves. The new season also opens up more possibilities for your travel dresses. As a travel journalist often splitting time between business meetings abroad and demanding sightseeing schedules, I’ve always leaned into dresses for that effortless look that can take me from day to night year-round. 

When it comes to fall dresses for travel, cinched-waist sweater dress looks and free-flowing maxis are just a few of my must-have items that find their way into my packing cubes. If you’re upcoming travel plans have you wanting to mix things up a bit, there’s a dress style out there with your name on it—no matter the temperature. From minidresses donned with tights to long-sleeved sweater maxi styles warm enough to leave your jacket at home, here are 40 fall dresses for every type of traveler. 

Best Fall Dress Deals for Travelers

Best Maxi Dresses

J.Crew Scoopneck Mixy Dress

J.Crew

Maxi dresses offer great versatility with a flowy silhouette that you can dress up or down. The seasonless option works well as a long or short-sleeved look with an ankle length that makes it easy to layer with leggings underneath it on cooler days. Gap’s Modern Rib Maxi T-Shirt Dress ($60) is the ultimate effortless look that can take you from day to night, with ribbed soft stretch cotton and slits at the hem for easy movement. When you’re gearing up for a night out, consider the Zesica Long-sleeve Sweater Dress (on sale for $36) since it’ll keep you warm on chilly evenings, and it comes in plenty of the season’s well-loved muted color palettes. 

Zesica Long-sleeve Sweater Dress

Amazon

Gap Modern Rib Maxi T-shirt Dress

GAP

Best Midi Dresses

Kranda Puff Long-sleeve Ruffle Midi Dress

Amazon

One of the best things about midi dresses is that their mid-calf to just-above-the-ankle length allows you to show off your favorite fall boots or flats. You can dress a midi style up or down with belts to cinch the waist and layer it with a cropped jacket or cardigan. Madewell’s Denim V-Neck Circle Dress ($168) is a perfect seasonal transitional piece made from 100 percent cotton with functional perks like pockets and a naturally cinched waist. Gap’s Linen-Blend Midi Shirtdress is a fall must-have that you can grab now for under $100, and I bet you’ll have no trouble adding the Mascomoda Long-sleeve Midi Dress, now $45, into your fall travel wardrobe. 

Mascomoda Long-sleeve Midi Dress

Amazon

Quince Cotton Gauze Midi Dress

Quince

Best Mini Dresses

Express Mini Sweater Dress

Express

Just because temperatures drop a bit doesn’t mean you have to hide your legs. Mini dresses are the fun, flirty cut for any fall fashion closet, and best of all, warmer fabrics are easily available to achieve your look. Take the Quince Mongolian Cashmere Short Sleeve Mini Dress, for example, with a buttersoft fabric that’s thick enough to keep you warm on cooler nights. If you’re gearing up for a girl’s night out or date, the Express Mini Sweater Dress ($78) offers all the allure of a bodycon dress with a mock neckline and elbow-length sleeves. Another pick to consider? PrettyGarden Long-sleeve Tie-waist Mini Sweater Dress, currently on sale for $32, thanks to a double-discount deal. 

PrettyGarden Long-sleeve Tie-waist Mini Sweater Dress

Amazon

Madewell Gathered Button-front Mini Dress in Floral

Madewell

Best Petite Dresses

J.Crew Elena Shirt Dress

J.Crew

Many brands are tapping into petite dress sizes, meaning you no longer have to plan for a trip to a tailor to buy your favorite new find (starting with the J.Crew Elena Shirt Dress, which is available in petite sizes). The Quince Cotton Mixed Media Tank Dress, $60, is the perfect wear-anywhere dress for petite travelers with its midi length and versatile style. For an evening look with pizzazz, the Chyrii Drop-waist Long-sleeve Midi Dress‘s trendy silhouette makes a great canvas for your favorite jewelry and accessories—and it’s only $46.  

Quince Cotton Mixed Media Tank Dress

Quince

Merokeety V-neck Polo Ribbed Knit Dress

Amazon

Best Plus-size Dresses

ScomChic Long-sleeve Sweetheart Neckline Mini Dress

Amazon

Inclusive fashion brands understand that no look should be restricted to one size fits all. Finding styles that work with your body type is possible–it’s just a matter of where to look. Over at Amazon, you can secure a travel-friendly travel dress in this ScomChic Long-sleeve Sweetheart Mini for only $29 (available in sizes up to 4XL). If you’re a fan of romantic patterns, the Torrid LoveSick Front-tie Tea-length Dress, just $50, is the perfect fall maxi for exploring new cities, while Anthropologie’s The Thea Short-sleeve Twofer Mini Dress is a splurge-erothy sweater dress that can be dressed up or down to match any trip itinerary. 

SheStarr Puff Long-sleeve Square-neck Empire-waist Mini Dress

Amazon

Anthropologie The Thea Short-sleeve Twofer Mini Dress

Anthropologie 

Best Tall Dresses

Banana Republic Tiered Midi Dress

Banana Republic

Don’t sacrifice hemlines and disappointing full-length fashion just because you’re tall. Look for helpful features like adjustable straps and silhouettes that highlight the waist and torso, like this Tiered Midi Dress from Banana Republic, currently on sale for $70, or Gap’s Denim Roll-cuff Midi Shirtdress, starting at $83, thanks to a limited-time deal, which features details like pleating at the waist and front slit on the flared bottom silhouette. Don’t forget about the tall-girl-approved PrettyGarden Long-sleeve Smocked Square-neck Tiered Maxi Dress at Amazon, for just $53. 

Gap Denim Roll-cuff Midi Shirtdress

GAP

Btfbm Long-sleeve Wrap Midi Dress

Amazon

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