Dresses That'll Carry You From Season to Season

(Image credit: Edward Berthelot)

published 17 June 2021

As fall rolls around, baking hot days and skin-baring clothes start to feel like a thing of the past. Summer's carefree, breezy dresses cater to a different frame of mind. As many of us return to offices and schools post-Labor Day, we'll be turning to fall uniforms that read a little more sophisticated than our summer mainstays. We're talking darker hues, subdued prints, and elongated hemlines—but early autumn weather will call for lighter textures and freer-flowing silhouettes, too. Paired with the right accessories—one of this year's it bags or statement baubles, for example— a fall dress can truly transcend any forecast or season. Ahead, we've got 17 to start shopping right now.

1/16

Staud Cotton Blend Midi-Dress

This khaki-colored dress has a relaxed fit and side slip pockets, marrying the ease of summertime dressing with the sophistication of a fall color palette.

2/16

Kate Spade Striped Midi Dress

This elbow-length striped dress reads summer all on its own, but paired with an oversized sweater and knee high boots, it will be on constant rotation as the season begins to turn.

3/16

Sea Gingham Cotton Midi-Dress

Gingham isn't just a summertime print. Wear this check dress well into fall, layered with a chunky cardigan and boots.

4/16

& Other Stories Mini Polo Dress

This thick knit polo dress is ideal for early fall days. Style it with your favorite low-top sneaker for a weekend on the go.

5/16

Everlane The Retro Jersey Polo Dress

Another polo dress for your Fall wardrobe. This one is machine washable and has a sophisticated contrasting collar. Style it with a cable knit over your shoulders, an ankle sock, and some loafers.

6/16

Proenza Schouler White Label Leather Shirtdress

Embrace autumnal leather weather with this sleek button-down shirt dress that can be worn for work or play.

7/16

Tory Burch Printed Broderie Anglaise Painter's Dress

What better time to wear this market fruit print dress than in harvest season?

8/16

Rebecca Taylor Ruched Osaka Dress

This silk midi-dress has a feminine ruched neckline and sweet pleat details. It's an elevated choice for fall wedding guest attire.

9/16

Wales Bonner Saint Catherine Denim Shirt Dress

Crafted from medium weighted denim, this button-down shirt dress can be worn comfortably on summer evenings and well into crisp fall days.

10/16

Rosetta Getty Floral Print Jersey Dress

This floral retro fabric dress is an investment, but with the right accessories, it can be worn for just about any and all occasions.

11/16

Nanushka Ayse Poplin Twist Midi Shirtdress

This sky blue dress has the ease of summer wear with the sophistication of fall silhouettes.

12/16

Ulla Johnson Selena Cotton-Blend Coverup Dress

There's no better fall color palette than chocolate and navy. Wear this puff-sleeve maxi-dress alongside ballet flats and a crossbody bag for a sophisticated work day look.

13/16

Tove Organic Cotton Poplin Midi Dress

This delicate ruched, tie-neck dress is made from organic cotton. It's breathable for warmer temps but substantial enough to wear through leaf-peeping season.

14/16

Lisou Lauren Mango Love Flower Silk Shirt Dress

Wear this flower power print dress all on its own, layer it under a blazer, or pop on a cozy knit.

15/16

Industrie Africa Studio 189 Pouf Sleeve Shirt Dress

This dress is made to order by local artisans who hand-weave linear patterns to reflect traditional West African prints.

16/16

The Frankie Shop Two-Tone Tennis Dress

Take summer tennis tournaments into fall with this sporty court-to-street drawstring waist dress.

Sara Holzman is the Style Director at Marie Claire, covering runway trends and tracking down the latest finds to buy and wear. When she’s not writing about fashion, she pens about the best places to jet-off to. Over her six years with Marie Claire, Sara has reported on the ever-evolving world of fashion— covering both established and emerging designers within the industry. Sara has held fashion positions at Lucky and SELF Magazine and was a regular contributor to Equinox’s Furthermore website, where she wrote across their style, wellness, and travel verticals. She holds a degree in Journalism from the University of Missouri, Columbia, and currently resides in Manhattan. Follow her along at @sarajonewyork.