The 14 Best Dresses for Fall Travelers Who Value Style and Comfort (2024)

Versatile, comfortable, and easy to pack—you’ll want to add these fall dresses to your packing list immediately.

Best Fit and Flare Dress for Fall: BloomChic Solid Pocket Rib Knit Ruffle Hem Dress

As the weather shifts away from crisp, refreshing temperatures to chillier pre-winter days, your travel wardrobe should follow suit. The Rib Knit Ruffle Hem Dress from BloomChic is perfect for cooler fall weather and colder destinations, made from a cozy knit fabric with long sleeves and a midi length. It comes in five warm fall shades, including dark green, burgundy, and chocolate.

Best Shirt Dress for Fall: Rory Maxi Shirtdress

You don’t have to pack away the linens as soon as summer ends. The Rory Maxi Shirtdress from Frank & Eileen can easily make the transition between seasons, with it’s maxi length and neutral color palette. If you prefer a slightly heartier material, the dress is also available in six colors of denim.Add a lightweight mock-neck shirt underneath for colder days or layer an oversized sweater on top for a trendy and functional outfit.

Best Wrinkle-Free Dress for Fall: Chico’s Travelers Classic Short Sleeve Maxi Dress

This machine-washable dress is designed for travel, made from wrinkle-resistant fabric that is perfect for packing and plane rides. The cap sleeve detail, maxi-length, and leg slit elevate the design from basic t-shirt dress to elegant closet staple. Available in regular and petite sizes.

Best Ultra-Cozy Dress for Fall: Pink Queen Loose Turtleneck Sweater Dress

If you’ve ever wished that you could wear your Snuggy to the airport, then this is the dress for you. The oversized fit and loose turtleneck feels more like you’re wrapped in your favorite knit blanket than dressed up for a day of travel. It’s designed to hit mid-thigh, so it can be worn as a dress with tights or as a long top.

Best Custom Dress for Fall: eShakti Custom Dress

Always have to tailor your fall dresses to get the right length? Skip that step by ordering eShakti’s Cotton Knit Midi Dress, which is made-to-order, so you can customize it to your size and height.

Best Athletic Dress for Fall: Title Nine Guthrie Dress

The competing demands on athletic wear make it difficult to find the perfect outfit—it has to be breathable, functional enough to move in, stylish, and warm enough for the autumn weather. Enter the Title Nine Guthrie Dress, a long sleeve athletic dress that can easily go from a morning jog to an afternoon of sightseeing. Styled with a mesh pocket in the front, the dress has the functionality of a sweatshirt without the bulk.

Best Silk Dress for Fall: Ellie Washable Silk Dress

Silk isn’t generally a very travel-friendly fabric—unless it’s the unique kind made by Amour Vert and featured in the Ellie Washable Silk Dress. This sustainable fabric looks and feels just like silk, but it’s machine-washable (and doesn’t wrinkle, making it great for travel).

Best Lightweight Dress for Fall: Madewell Lightspun V-Neck Midi Dress

Ultra-soft and ultra-stylish, travel clothes don’t get much better than the Lightspun V-Neck Midi Dress from Madewell. The gauzy fabric is flowy and breathable, with a simple silhouette and open back. The woven texture lends itself to travel, easy disguising any wrinkles it may accrue in your checked bag. Available in sizes XXS to XXL and 1X to 4X.

Best Hoodie Dress for Fall: Fleece Lined Hoodie Dress

Available in every color of the rainbow and in sizes ranging from small to 3XL, this fleece-lined hoodie dress is a stylish option for those chilly mornings when ‘coziness’ is the top outfit criteria. Pair it with some extra fuzzy socks to complete the look.

Best Flannel Dress for Fall: L.L. Bean Flannel Tunic Dress

Flannel and plaid are both staples of the season, and this dress from L.L. Bean combines the best of both. Made from 100% cotton flannel, this dress is made to be both comfortable and durable, with a relaxed fit that can be worn as-is or cinched in with included tie.

Best Cashmere Dress for Fall: Quince Mongolian Cashmere V-Neck Midi Dress

It may seem like back-to-basics with this midi-length sweater dress from Quince, but its the small details that make it a winner. Made from 100% Grade-A Mongolian cashmere, its extra-soft for long travel days and perfectly warm for the freezing plane cabin. It’s easily styled with a casual jean jacket for day or elevated with some travel-friendly heels for a night out.

Best Waffle Knit Dress for Fall: LILLUSORY Women Pullover Sweater Maxi Dresses

A dressed-up take on the classic Henley, this waffle knit midi-dress comes in ten colors, with an effortless slouchy silhouette, drop shoulders, and statement buttons down the neckline.

Best Maternity Dress for Fall: Paisley Sage 2 in 1 Maternity & Nursing Dress

Having the right travel clothes while pregnant can make or break a trip. This 2-in-1 option can be worn while pregnant, with a billowing jersey skirt that allows room for growth without being too long or cumbersome, or while nursing. The cable-knit detail down the arm and muted sage color make it perfect for fall, and the attached crop sweater lifts to reveal a built in nursing top.

Best Jumpsuit for Fall

For travelers who aren’t into dresses but don’t want to feel restricted, there is the YESNO Wide Leg Jumpsuit. The loose design and apron-style front combines the stylistic elements of sundress with the security of a pair of pants. With fifteen colors to choose from, you won’t have any trouble matching these overalls to your favorite fall sweater.

All of the products featured in this story were hand-selected by our travel editors. Some of the links featured in this story are affiliate links, and SmarterTravel may collect a commission (at no cost to you) if you shop through them.

Caroline Morse-Teel contributed to this article.

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