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Winter Maxi Dresses Are Officially A Thing—Shop 12 Cute Picks

The phrase “winter maxi dresses” seems inherently oxymoronic. Because breezy silhouettes should be reserved for the calendar’s warmest months, right? Because summer is the only season where comfy-cute dressing is a priority, and winter is strictly for bundling up in chunky knits, oversized scarves and warm AF coats, right? (You might want to think again, actually.)

Though this logic is commonly held, your favorite retailers have taken to challenging it. They’ve stocked up on maxi dresses en masse—in the middle of winter—leaving winter maxi dresses feeling less oxymoronic than they ever have before. One simple fact has become undeniable: Winter maxi dresses are here, and they promise to leave our winter wardrobes way more dynamic than they found them.

I first encountered a winter maxi dress in the wild in December, when a friend of mine wore one to dinner. The dress was floor-length, and its flowy cut screamed of summer. But its thick, forest-green fabric communicated otherwise; this maxi was strictly intended for cold weather. The piece perplexed—and then delighted—me. I’d never before seen a maxi dress look so at home in a genuinely chilly environment.

I spent the next few days perusing my go-to retailers for similar pieces, and I found them—in spades. Zara, Anthropologie, Eloquii, Free People—and more—had collectively embraced the winter maxi dress trend. I saw floor-length striped gowns, dark floral prints, elongated plaid button-downs and sweater dresses that grazed the ground.

The most astounding part of this discovery wasn’t just that winter maxi dresses existed—it was that they existed in truly diverse varieties. The winter maxi dress selection I came across was far more exciting than the ones I’d seen in the summer. It became clear to me that winter maxi dresses weren’t just redefining what winter fashion looked like—they were reimagining what maxi dresses looked like, too.

Ahead, you’ll find a visual (and shoppable) guide to the winter maxi dress in all its statement-making glory. And the best part of all of this? You can layer all kinds of tights, leggings and pants under most of these winter maxi dresses, so you can probably stay warmer in them than you can in your go-to trousers. Talk about a winter fashion win.

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STYLECASTER | Winter Maxi Dresses

Courtesy of Reformation.

Mandi Dress

Reformation knows a thing or two about a good dress, and this emerald velvet pick is a holiday party must-have.


STYLECASTER | Winter Maxi Dresses

Courtesy of Who What Wear.

Puff Long Sleeve Dress

Y’all, do NOT sleep on Target’s Who What Wear Collection. This spotted dress is one of my absolute winter favorites.


STYLECASTER | Winter Maxi Dresses

Courtesy of Eloquii.

Boat Neck Long Satin Dress

Satin isn’t just for neutrals, people, and this gorgeous green number is proof. I’d especially love this paired with some patterned knee-high boots for contrast.


STYLECASTER | Winter Maxi Dresses

Courtesy of Christy Dawn.

Bowie Dress

I used to be wary of long black dresses, but now I see them for what they are: versatile AF, not witchy. That is, unless you’re going for winter coven realness, in which case, please proceed.


STYLECASTER | Winter Maxi Dresses

Courtesy of Reformation.

Kellie Dress Es

I’m a sucker for a dark floral, and this dress is just begging to be worn with my cutest accessories.


STYLECASTER | Winter Maxi Dresses

Courtesy of Reformation.

Kellie Dress

Even though it looks completely different, this dress is the exact same as the one above it. In the solid Cinnamon colorway, you can really see the detail in that beautiful tiered maxi skirt.


STYLECASTER | Winter Maxi Dresses

Courtesy of TopShop.

Ruffle & Pleat Long Sleeve Maxi Dress

Prints, pleats and ruffles? Who says we can’t be a little over-the-top every now and then? This zebra dress is definitely a standout, but you can dress it down with black boots and a black leather trench.


STYLECASTER | Winter Maxi Dresses

Courtesy of Saturday/Sunday.

Taylor Flounced Maxi Dress

Available in four colorways, this soft, stretchy ribbed maxi dress is ideal for everyday wear. It’s the kind of piece you can cozy up in while you work from home, then keep it on with some great accessories for dinner with a friend.


STYLECASTER | Winter Maxi Dresses

Courtesy of Lulu’s.

True To Love Chiffon Wrap Maxi Dress

Another gorgeous dark floral, to be dressed up or down. Love the warm hues in this one!


STYLECASTER | Winter Maxi Dresses

Courtesy of AllSaints.

Leowa Pleated Dress with Wool Blend Sweater

I’m obsessed with these dresses by AllSaints, which come with a sweater overlay to create the illusion of a skirt and top. So clever!


STYLECASTER | Winter Maxi Dresses

Courtesy of Eloquii.

Satin Maxi Wrap Dress

Whoever said pink isn’t a winter shade was seriously disturbed! I’m head over heels for this stunning satin wrap dress, which also comes in a beautiful, vibrant green.


STYLECASTER | Winter Maxi Dresses

Courtesy of City Chic.

Cheetah Print Maxi Dress

Leopard print is a year-round staple, and this beautiful dress features a saucy leg slit so you can show off, even in the cold.

A version of this article was originally published in 2018.

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