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The 22 Best Winter Dresses to Ditch Your Sweats for This Season

Yes, it is possible to look cute in cold weather.

Headshot of Gaby KeiderlingBy Gaby Keiderling
best winter dresses

Getting dressed in the winter can be depressing. Chunky sweaters, though undeniably chic, have lost their novelty, you have to wear a puffer jacket everywhere you go, and you only have so many high-waisted leggings that haven’t pilled at this point. It’s time for something new—something cozy and comfy but flattering at the same time. The solution? A winter dress.

The best winter dresses are seasonal staples and come in many forms, from long-sleeved midis to capped-sleeved minis done in plush materials like wool, velvet, and cashmere. And thanks to some of our favorite designers, today’s silhouettes are more eye-catching than ever. Take, for example, Alice + Olivia’s date night-ready, faux leather number or Simon Miller’s colorful knit dress perfect for every casual-yet-stylish outing on your calendar. Whether you’re seeking an option that’s laidback, formal, or somewhere in between, there’s a winter dress that can rise to the occasion. Not to mention, you can fashionably add extra warmth to your pick by throwing on a pair of tights, over-the-knee boots, and a fabulous wrap coat.

The search for the perfect dress may seem overwhelming, but never fear. Ahead, shop the 22 best winter dresses to elevate your wardrobe this season.

Best Faux Leather Dress

Alice + Olivia Chara Pleated Mini Dress

Chara Pleated Mini Dress
Best Faux Leather Dress

Alice + Olivia Chara Pleated Mini Dress

Now 75% Off
$99 at Alice and Olivia

Alice + Olivia’s Chara vegan leather dress will bring some edge to your cold-weather lineup. Style it with opaque tights and combat boots, and you’re ready to rock and roll.

MaterialsPolyester, nylon, elastane
Sizes Available0-14
ColorsBlack, White
Best White Dress

Rag & Bone Asher Midi Dress

Asher Midi Dress
Best White Dress

Rag & Bone Asher Midi Dress

Now 59% Off

For those who love a crisp winter white dress, Rag & Bone carries this stretch knit midi that aims to hug your body in all the right places. Another perk: Its trendy square neckline is great for showing off your favorite stack.

MaterialsViscose, nylon, spandex
Sizes AvailableXXS-L
ColorsIvory, Black
Best Ribbed-Knit Dress

Simon Miller Wells Long-Sleeve Dress

Wells Long-Sleeve Dress
Best Ribbed-Knit Dress

Simon Miller Wells Long-Sleeve Dress

This ribbed-knit midi from Simon Miller provides so many styling possibilities. Leave it free-flowing or cinch it at the waist with a leather belt or corset to create definition.

MaterialsModal, spandex
Sizes AvailableXXS-XXL
ColorsSepia Brown
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Best Sweater Dress

RtA Akamu Sweater Dress

Akamu Sweater Dress
Best Sweater Dress

RtA Akamu Sweater Dress

Now 55% Off

RtA puts a sexy spin on the traditional sweater dress with this loose-weave number. To ward off any breeze, layer a slip underneath.

MaterialsCotton, acrylic, wool, polyamide
Sizes AvailableXS-L
ColorsWhite, Black
Best Casual Dress

Free People Mont Blanc Mini Dress

Mont Blanc Mini Dress
Best Casual Dress

Free People Mont Blanc Mini Dress

Free People is the queen of everything cozy and cute, like this vintage-inspired sweater dress featuring a cheeky front-zipper detail.

MaterialsPolyester, cotton
Sizes AvailableXS-XL
ColorsVintage Blue Combo, Tab, Red Jasper
Best With Subtle Detailing

Rouje Kaila Dress

Kaila Dress
Best With Subtle Detailing

Rouje Kaila Dress

Rouje delivers this supremely elegant midi dress, boasting dainty rose-shaped fasteners for subtle retro flair.

MaterialsWool, polyamide
Sizes Available34-42
ColorsBlack
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Best Denim Dress

Mother The Cover Up

The Cover Up
Best Denim Dress

Mother The Cover Up

Now 50% Off

On the dreariest afternoons, this bubblegum-pink denim dress is the serotonin boost you need. Throw on your favorite pair of sneakers to nail a cute everyday look.

MaterialsCotton, polyester, elastane
Sizes AvailableXS-XL
ColorsQuartz Pink
Best Cutout Dress

Jonathan Simkai Kathryn Midi Dress

Kathryn Midi Dress
Best Cutout Dress

Jonathan Simkai Kathryn Midi Dress

Maybe you want some cutouts to spice things up. In that case, this bold midi dress is just for you. Its crystal chain hardware at the waist is also a fun addition.

MaterialsRayon, nylon
Sizes AvailableXS-XL
ColorsBlack
Best Slip Dress

Maison Essentiele 90s It Girl Chemise

90s It Girl Chemise
Best Slip Dress

Maison Essentiele 90s It Girl Chemise

We know, it’s chilly out. But when paired with an oversized faux fur coat and tall boots, this mini slip dress will create the chicest GNO outfit that won’t cause you to totally freeze. For more casual events, it’s great to layer with chunky sweaters and turtlenecks.

MaterialsSilk
Sizes AvailableXS-XL
ColorsBlack, Blue
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Best Ruffled Dress

Cleobella Lacey Mini Dress

Lacey Mini Dress
Best Ruffled Dress

Cleobella Lacey Mini Dress

Despite its sheer lace fabric, this dress offers a little extra coverage via a full lining, high neckline, and three-quarter length sleeves. Jazz it up with some sparkly earrings and a glitzy clutch if the occasion calls for it.

MaterialsPolyester
Sizes AvailableXS-XL
ColorsBlack
Best Printed Dress

Zadig & Voltaire Refla Minidress

Refla Minidress
Best Printed Dress

Zadig & Voltaire Refla Minidress

If playful patterns are your thing, this Zadig & Voltaire mini is a whimsical yet tasteful pick.

MaterialsViscose
Sizes AvailableXS-M
ColorsEcru/multicolor
Best Mini Sweater Dress

Reformation Libra Knit Dress

Libra Knit Dress
Best Mini Sweater Dress

Reformation Libra Knit Dress

Thigh-high boots are the move with this knit mini dress. The turtleneck and long sleeves feel very on-brand for cooler temps, while the subtle leg slit helps you show off a bit of skin.

MaterialsLyocell, spandex
Sizes AvailableXS-XL
ColorsBlack, Oxide
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Another Great Sweater Dress

Sanctuary Mock Neck Sweater Dress

Mock Neck Sweater Dress
Another Great Sweater Dress

Sanctuary Mock Neck Sweater Dress

Now 55% Off

Is it just me, or does this richly colored number make you want to have a mocha in hand, stat? I love how the rib knit accents really pop on this one, too.

MaterialsAcrylic
Sizes AvailableXXS-XXL
ColorsSpice
Best Wedding Guest Dress

Sandro Paris Lucianita Mini Dress

Lucianita Mini Dress
Best Wedding Guest Dress

Sandro Paris Lucianita Mini Dress

With its delicately embroidered fabric and bejeweled Peter Pan collar, this gorgeous style is a stunning winter wedding guest dress option. Pair it with some heels or ankle boots, and when you want to dress it down, try some chunky loafers.

MaterialsPolyester, viscose, polyamide
Sizes AvailableXS-XL
ColorsNavy Blue
Best Wool Dress

Iceberg Ribbed Midi Dress

Ribbed Midi Dress
Best Wool Dress

Iceberg Ribbed Midi Dress

Now 50% Off

Italian luxury fashion house Iceberg has been known for its striking designs since 1974, with this sunny midi dress being no exception. It’s also made with merino wool, which is crafted to be super soft, warm, and moisture-wicking.

MaterialsMerino wool
Sizes AvailableS,M
ColorsYellow, Black
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Best Floral Dress

The Kooples Short Floral Dress

Short Floral Dress
Best Floral Dress

The Kooples Short Floral Dress

Now 55% Off

Florals for winter? Yes please! The dark floral pattern on this silky, tailored option is especially fitting for the season.

MaterialsSilk, viscose
Sizes Available0-3
ColorsBlack, White
Best Fitted Dress

Ganni Mini Dress

Mini Dress

Done in a cool textured finish, Ganni’s mini dress has a flattering, fitted shape and ruffled, elbow-length sleeves that are feminine and classic. The scoop neckline isn’t too revealing, either, in case that’s something you’re after.

MaterialsRayon, polyamide, elastane
Sizes AvailableXXS-XL
ColorsKelly Green
Best Belted Dress

Scanlan Theodore Belted Long-Sleeve Midi Dress

Belted Long-Sleeve Midi Dress
Best Belted Dress

Scanlan Theodore Belted Long-Sleeve Midi Dress

Choose from three different hues with this belted midi dress. Knit from crepe, it should be comfortable, warm, and breathable.

MaterialsViscose, polyamide
Sizes AvailableXS-L
ColorsLilac, Powder, Navy
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Best Shirt Dress

Michael Lo Sordo Wrap Maxi Shirt Dress

Wrap Maxi Shirt Dress
Best Shirt Dress

Michael Lo Sordo Wrap Maxi Shirt Dress

The pajamas-as-streetwear aesthetic is still in, and this silky wrap shirt dress takes it to a whole new level. Simply slide into some heels to complete the comfy-chic look.

MaterialsSilk-satin
Sizes Available2-14
ColorsBlack
Best for Black Tie Events

Nili Lotan Katie Lamé Gown

Katie Lamé Gown
Best for Black Tie Events

Nili Lotan Katie Lamé Gown

Now 65% Off

We did say velvet, didn’t we? If you have a soirée or gala to attend, a sparkling velvet gown from Nili Lotan will surely turn heads.

MaterialsViscose, nylon
Sizes AvailableXS-L
ColorsGold
Headshot of Gaby Keiderling
Gaby Keiderling

Gaby Keiderling is a New York based writer, working on fashion, lifestyle, travel, and sports features. She also covers celebrity style for Esquire's 'Get Ready with Me' franchise. Her work can also be seen in Vogue, Harper's Bazaar, and more. Sometimes you can spot her around the West Village, out on a walk with her dog Sneakers.

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