20 Best Winter Dresses 2022: Cozy and Versatile Winter Dresses

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You'll wear them on repeat.

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.

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.

Graduate from a coordinating groutfit to a sensuous lounge dress when your only winter plans are hanging at home. This best-seller from Skims is double-lined for a smoothing effect (and it's quite cozy).

Sizes: XXS–4X

Here's a little dress with huge winter styling potential from Hill House Home's most recent collection. As one satisfied shopper writes, "The tartan is a nice, thick, sturdy-feeling flannel material that's perfect for winter and gives this dress some loft." Reviewers do mention that it's a true mini, so make sure you have reliable tights—or even fleece-lined leggings—ready to wear underneath.

Sizes: S–2XL

Stine Goya's groovy printed knit is first on Maguire's list of recommendations—and ours, too. It's warm but definitely not stuffy, and, when it's time to pull on a coat, the print is an invitation to play around with contrasting patterns and textures.

Sizes: XXS–XL

We'll get straight to the point: With a blend of wool and recycled materials, plus oversized sleeves with a flutter hem, this fitted dress is a wallet-friendly grail.

Sizes: XXS–XL

The best floral dresses are season agnostic, like this spring to fall to winter dress. I'm writing from experience: I own this dress in two prints, and I wear both constantly. To make them more winter-appropriate, I'll either add a thin long-sleeve shirt underneath or a half-tucked sweater on top.

Sizes: XXS–XXL

If you care about versatility above all, this winter dress practically has your name stitched into the seams. Wear it buttoned all the way up, and it's a flannel shirt dress. Add a turtleneck and jeans underneath, and it's an extra-cozy shacket.

Sizes: XXS–XL

The most elevated winter options feel like blanket dressing but look completely refined. For example, this paneled Chloé dress in a wool and cashmere knit that rivals your most-loved fireside throw blanket.

Sizes: XS–XL

You'll get year-round mileage out of this one hundred percent silk slip, but it's especially suited to winter layering in this berry red shade. Try it with a printed long-sleeve bodysuit underneath one day, and a chunky knit sweater on top the next.

Sizes: XS–XL

Here's another of Maguire's recommendations for brightening winter days with a one-and-done dress. This velvet maxi comes in an abstract print that feels seasonal but totally unique.

Sizes: XS–L

There's so much more to this dress than the two-day Prime shipping. A few of our top details: the fluid knit jersey fabric, the convertible straps (to cinch your waist or play up your shoulders), and the inclusive sizing.

Sizes: 34–56

Fans of Sézane's famous cardigans will love a sweater dress knit from the exact same (and sustainably-sourced) material. Those who haven't yet been introduced will consider this their gateway piece.

Sizes: XS–XXL

Presenting the most colorful of Maguire's winter dress picks. If there's any dress to brighten your mood on this list, it's this candy-stripe midi.

Sizes: 0–16

Éterne's mini sweater dresses are just like its loungewear—that is, minimal and enviably comfortable. While this dress is worthy of its own outfit with thermal tights and a statement jacket, it's also thin enough to layer under another one of the long-sleeve dresses on this list.

Sizes: XS–XL

Ganni's fall collection with Levi's wasn't just about jeans, though their takes on wide-leg jeans are too good to skip. The duo also released a denim midi dress made from organic cotton and plant dyes that I can confirm is soft, slightly stretchy, and great with a cowboy boot.

Sizes: XS–3XL

Make your innermost layer your most exciting one. The swatches of mismatched fabric peeking out from under your coat will make the full dress reveal feel like a moment.

Sizes: XS–L

Velvet dresses with bows and tiers are more party circuit material. If you want to bring the fabric's richness into your everyday, try a dress that remixes it in a cool tie-dye print.

Sizes: XS–XL

Come for the exaggerated sleeves, stay for the knit with a mid-weight you can savor now and in transitional weather (with fewer layers).

Sizes: XXS–XL

Thin, fitted dresses aren't off-limits when it's cold outside. In fact, when they come in a stretch jersey like Isabel Marant's, they're just the right thickness to layer over HeatTech turtlenecks and leggings. The best of both worlds, truly.

Sizes: FR34–FR44

You'll still get the soft, swaddled feeling of a cozy sweater dress with this Reformation number. But it's in a clingier cashmere knit that, with a low-slung heel or a tall boot, feels infinitely more elevated (and worthy of being seen).

Sizes: XS–XL

On the hanger, this looks like a flowy dress with stripes of bohemian print. Putting it on, it's also one of the most comfortable winter dresses you could wear with its stretchy smocked bodice. All you need to make it an outfit is a pair of knee-high boots.

Sizes: 0–14

Halie LeSavage is the fashion commerce editor at Harper's BAZAAR. Her style reporting covers everything from reviewing the best designer products to profiling emerging brands and designers. Previously, she was the founding retail writer at Morning Brew and a fashion associate at Glamour.

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