Upgrade Your Cold-Weather Wardrobe With These 25 Winter Dresses

Lauren Caruso
Winter Dresses
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In the summer, picking out a new dress is simple: You grab the most lightweight one you can find, and then you put it on. But when the temps go down and the number of layers required to even think about opening your front door go up, picking out a dress can become, well, tricky. You have to choose one that’ll look good with a pair of tights (or fishnets, if you dare), or something knit that’ll lay nicely over a pair of jeans. Or, if you’re looking for something that can double as both workwear and party-appropriate, you’ll have to do some serious hunting.

MORE: 20 Best Fur Stoles to Wear All Winter Long

But restocking your wardrobe doesn’t have to be stressful. We found 25 cute winter dresses—including a mock-neck knit iteration, a work-ready floral crepe dress, and a red velvet number that’s perfect for every event from now till March—to add to your closet now. Oh, and if you’re really not sure how to wear them in the winter, check out these styling tricks that’ll double your cold-weather wardrobe STAT.

MORE: 27 Zara Pieces at the Top of Our Winter Wish Lists

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J.O.A. Striped Long Sleeve Dress, $95; at J.O.A.

Photo: J.O.A.

& Other Stories Zebraic Frilled Dress, $115; at & Other Stories

Photo: & Other Stories

COS Merino Roll-Neck Dress, $125; at COS

Photo: COS

Jacquard Pinafore Dress, $125; at Topshop

Photo: Topshop

Apiece Apart Milagro Knit Dress, $425; at The Dreslyn

Photo: The Dreslyn

Wilfred Free Verster Dress, $60; at Aritzia

Photo: Aritzia

New Look Plus Velvet Wrap Front Dress, $43; at ASOS

Photo: ASOS

Zara Crossover Velvet Dress, $49.90; at Zara

Photo: Zara

AYR The Collapse Dress, $395; at AYR

Photo: AYR

Chinti and Parker Color Block Dress, $495; at Net-a-Porter

Photo: Net-a-Porter

Cienne The Hudson Dress, $385; at Cienne

Photo: Cienne

Club Monaco Kimana Dress, $595; at Club Monaco

Photo: Club Monaco

Reformation Gemma Dress, $278; at Reformation

Photo: Reformation

Express Sequin and Chain Mail Shift Dress, $108; at Express

Photo: Express

Everlane Cashmere V-Neck Midi Dress, $155; at Everlane

Photo: Everlane

Keepsake Listen Out Long Sleeve Pleated Dress, $189; at Pixie Market

Photo: Pixie Market

H&M Short Seuqined Dress, $69.99; at H&M

Photo: H&M

Monki Keyhole Neck Velvet Skater Dress, $38; at ASOS

Photo: ASOS

Ganni Akina Crepe Dress, $165; at Need Supply

Photo: Need Supply

Oak + Fort Dress G16, $108; at Oak + Fort

Photo: Oak + Fort

Pixie Market Mock Neck Dress, $82; at Pixie Market

Photo: Pixie Market

Public School Toma Dress, $450; at Shopbop

Photo: Shopbop

A.P.C. Robe Puccini, $520; at Need Supply

Photo: Need Supply

7115 by Szeki Relaxed Boat Neck Dress, $178; at 7115 by Szeki

Photo: 7115 by Szeki

Zara Frilled Dress, $39.90; at Zara

Photo: Zara

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