15 Stylish Winter Dresses for Cold Temps, Hot Parties, and Everything In-Between
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Dresses always seem to come to mind when shopping, regardless of the season. Winter, in particular, can be pretty tricky to shop for. Between bundling up for temperature drops to needing something that looks fresh at the holiday parties you’re headed to, the pressure is on.
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Brands like Alexander McQueen and Fear of God made it slightly more approachable this year, sporting classic trends that emphasized the importance of everlasting style. Swedish brand BITE also followed suit, showcasing minimal designs cast in winter tones and constructed with some of the finest materials. In short, this season is less about bold trends and all about the classics.
From cozy full-knit sweater dresses for dinners to sequin minis for cocktails; gorgeous gowns for those holiday parties to simple pieces that will get noticed every time — there’s a winter dress here for every occasion.
The Drop Renata Rib Midi Dress
Soft and oversized, it’s just what you want in the winter to snuggle up in during those dreadfully cold days and even colder nights. That’s where The Drop’s Renata Rib Midi Dress comes in. This might become your daily go-to selection made from a soft fabric and ranging in sizes. (Currently available in sizes XXS-5X)
Skims Fits Everybody Mock Neck Sleeveless Maxi Dress
They say if it works, buy one in every color. That might be the case with the Skims Fits Everybody Mock Neck Sleeveless Maxi Dress. The classic silhouette comes in a range of sizes, is made of ultra-stretch fabric for comfort, and comes in a range of colors for whatever occasion you find yourself in this winter. (Currently available in sizes XXS-3X)
Remain Birger Christensen Black Sheer Maxi Dress
Beige tones are a great neutral as a base layer when needing to bundle up during colder months. This Remain Birger Christensen Black Sheer Maxi Dress is excellent when paired under another beige jacket for some tonal play. (Currently available in sizes XXS-XL)
Free People Night Gaze Mini
It might be cold outside, but you’re ready to hit the town! In that case, there is nothing quite like a Free People Night Gaze Mini to put you in the mood for the holidays. If you’re looking for a bit of warmth, pair it with a black turtleneck and tights. You’ll be much warmer and still look effortlessly chic. (Currently available in sizes XS-XL)
Anrabess Turtleneck Sweater Dress
Cherry red is the color of the season, so if you’re looking for a dress to don at those holiday gatherings, look for a punch of color. The Anrabess Turtleneck Sweater Dress features long sleeves and a ribbed design cut at the thigh. With considerable stretch, it’s a beautiful option to feel cozy without being constricted.
Mac Duggal Metallic Bateau Neck Column Gown
As temperatures drop, the parties get hot. Whether you’re headed to a chic cocktail night with friends or a holiday party where your colleagues are in attendance, this Mac Duggal Metallic Bateau Neck Column Gown is a stunner that will have everyone gawking at your look. (Currently available in sizes 0-14)
Free People Theo Sweater Midi
It’s sweater weather, and what better way to engage in the season than with a sweater dress? The Theo Sweater Midi features a relaxed, shapeless silhouette for unrestricted comfort and a boxy cut with draped arms, perfect for layering anything underneath. Dare we say test out a sweater-on-sweater moment in this? (Currently available in sizes XS-XL)
Reformation Gray Aara Maxi Dress
Winter is the perfect time to cozy up in one of the sexiest trends: the nighty-style slip dress. Whether it’s to grab drinks for a date out, or a night in with champagne, the Reformation Gray Aara Maxi Dress is a standout selection. (Currently available in sizes XS-XL)
Jean Paul Gaultier Printed Stretch-Tulle Midi Dress
There aren’t many brands that can compare in ingenuity and pure style to Jean Paul Gaultier. They are the blueprint for many of fashion’s current favorite designers. So, if you’re going to a party and want to flex a little originality, this Jean Paul Gaultier Printed Stretch-Tulle Midi Dress is calling your name. (Currently available in sizes XXS-XL)
Third Form Black Line Up Maxi Dress
We’ve all seen the sheer trend take celebrities by storm. However, in the winter that can be a bit difficult to get away with. This Third Form Black Line Up Maxi Dress gives you the best of both worlds, with full coverage designed in a sheer knit. (Currently available in sizes XS-L)
ASTR the Label Plissé Maxi Dress
A broad shoulder is the ultimate display of power, and what better way to showcase this than in comfort? ASTR the Label’s Plissé Maxi Dress not only sports the broad shoulder but features a lustrous plissé fabric that has some stretch to fit your curves. (Currently available in sizes XS-XL)
Reformation Black Casette Maxi Dress
A classic silhouette with simple, intriguing details like the cowl neck, flared hem, and ruching side seams, the Reformation Black Casette Maxi Dress is a great option with everlasting style and appeal. For colder temps, try layering a leather trench for something classy with a slight edge (Currently available in sizes 0-12)
BerryGo V Neck Ruffle Velvet Wrap Dress
There’s nothing quite as comfortable as a wrap dress — adjustable to your curves and can be tied as tight or loose as you want. The BerryGo V Neck Ruffle Velvet Wrap Dress is a great holiday selection if you plan on having an extra cookie (or two) at those holiday gatherings. (Currently available in sizes 0-14)
Fear of God Essentials Cotton Blend T-Shirt Dress
We’ve all upsized that t-shirt purchase for a cozy at-home option. But what’s better is a t-shirt actually designed as a dress. The Fear of God Essentials Cotton Blend T-Shirt Dress is just that, becoming the ultimate cozy selection and made of high-quality fabric for a soft touch. (Currently available in sizes XXS-XXL)
St. John Sequin Turtleneck Gown
Hear me out here. I’ve owned several items from St. John for years now, and much like this Sequin Turtleneck Gown, they are all classic styles that never get old. Whether it’s the sequin jumpsuit or my leather pants, I get compliments every time I break them out, and the quality is nothing short of immaculate (I’ve gotten down on the dance floor several times, and there isn’t a stitch out of place on anything). All this to say, if you’re going to invest in something bold yet classic for the holidays, let it be this dress. It will never go out of style. (Currently available in sizes 0-18)
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