Cozy and Versatile Winter Dresses

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a model wears a black sweater dress at fashion week in a roundup of the best winter dresses 2022

Tyler Joe

At the height of winter, I want to be swaddled. In other words, I want to be wrapped from head to toe in blanket-adjacent cashmere, wool, or a blend of the two, preferably in a setting where Après-ski clothes are the uniform. Most years, the best winter dresses to satisfy my craving for all things soft and blizzard-proof are equally straightforward: warm, comfortable, and weather-appropriate.

But this year, I feel an urge level up from simply cozy and cute winter dresses to something more considered. Designers are right there with me. Caroline Maguire, fashion director at Shopbop, tells BAZAAR the latest slate of long-sleeve sweater dresses are more adventurous than past seasons. While cuddly knits are still very much a wintertime staple, “We’re seeing designers play up this effortless look with bold colors and fun prints—the perfect way to lighten up winter’s gloomiest days!” she says.

Taking note of Proenza Schouler’s tie-dye velvet or Olivia Rubin’s hypnotic stripes is only the beginning. Outfit ideas involving even the most mesmerizing of winter dresses can start and end at tights and a tall boot—classic at best, formulaic at worst. Maguire has a semi-controversial favorite styling hack for something different: pulling on a sweater dress over denim. “It’s the perfect way to freshen up two classic silhouettes, not to mention the whole layered look is key for winter, adding dimension and extra warmth to an outfit,” she explains. If that’s a Y2k bridge too far, try half-tucking a chunky sweater into a belt over a tighter dress to play up the different shapes.

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Once your pick of the 20 best winter dresses below arrives, there’s a universal final layering tip Maguire recommends: “Throw on an oversized top coat and a pair of chunky, lug-sole boots to really lean into this cozy yet upgraded look.” Done and done.

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Best Printed Dress

Stine Goya

Chiara Dress

Best Dress Under $200

& Other Stories

Fitted A-Line Wool Knit Dress

Best Floral Dress

Dôen

Kaira Dress

Best Shirt Dress

Rails

Jaro Coat

Best Luxury Dress

Chloé

Wool and Cashmere Maxi Dress

Best Slip Dress

Cuyana

Silk Slip Dress

Best Patterned Dress

3.1 Phillip Lim

Kaleidoscope Crushed Velvet Flare Dress

Best Lounge Dress

SKIMS

Fits Everybody Dress

Best Dress on Amazon

Altuzarra

Masika Dress

Best Sweater Dress

Sézane

Angelita Dress

Best Striped Dress

Olivia Rubin

Rowen Dress

Best Dress for Layering

Éterne

Off-White Long Sleeve Minidress

Best Denim Dress

Ganni

Shirt Midi Dress

Best Patchwork Dress

Ulla Johnson

Almira Knit Midi Dress

Best Velvet Dress

Proenza Schouler

Tie-Dye Velvet Dress

Best Fitted Dress

Isabel Marant

Jenny Midi Dress

Best Cashmere Dress

Reformation

Evan Cashmere Sweater Dress

Best Mini Dress

Hill House Home

The Cher Dress

Best Smocked Dress

Sea

Adella Dress

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