It’s easy to fall into a style rut amid bitterly cold temps—but that’s where the best winter dresses come in. The perfect additions to your arsenal of low-effort pieces (looking at you, shirtdresses and chunky sweaters), these pieces will keep your outfits fresh and your getting-ready process as easy as possible. What more could you ask for this time of year?
Start by taking stock of the picks already in your closet—and the ones you wish you had on hand, like sparkly midis, velvet maxis, and sweaterdresses. Since the season is one of polar opposites—holiday parties and cozy days at home—it’s nice to have a few picks in your arsenal that pull double duty. Our favorites have major styling potential, courtesy of your winter capsule wardrobe essentials, including chic tights and tall boots. If you’re going to start somewhere, we suggest a new cashmere knit or a trendy jewel-toned party number. So let this be the year you treat yourself to some of the best winter dresses for women, all hand-selected by our style editors.
Glamour’s winter dress edit
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Naadam Signature Cashmere Turtleneck Dress
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The sweaterdress
Very few items will work harder in your winter wardrobe than sweaterdresses. Not only are they a one-step outfit that requires basically no effort, but they’re a truly stylish option for the colder months. Whether it’s an oversized jumper you can wear with suede boots and fleece-lined tights or a timeless rib-knit to layer under your favorite winter coat, the versatility may just surprise you.
The velvet dress
Every well-dressed woman needs at least one velvet dress in her arsenal. Perfect for seasonal gatherings and parties, it’s comparable to the classic LBD in terms of versatility. Apart from being a luxurious, textural choice for dinner dates and dressed-up gatherings, it’s a true wear-with-anything style that works as a foundation for any occasion-worthy ensembles.
The long-sleeve dress
Free-flowing, cuffed, second-skin-like—there are so many types of long-sleeve dresses to choose from, and now is the perfect time to invest in your lineup. From knee-length midis you can wear to work to body-skimming maxis that double as loungewear, these different approaches will all help you create a seasonally appropriate outfit on the fly.
The turtleneck dress
It’s all about high necks this season, and a good turtleneck dress walks the line between practical and stylish. Beyond the cozy collar keeping you warm through particularly chilly conditions, this silhouette offers a sleek, sophisticated look that will take you from the desk to drinks or dinner with ease. If you’re looking for a foolproof layering look, opt for fitted styles to wear under denim layers or V-neck shirts to highlight the high neckline.
The plaid dress
Each winter, there’s a pattern that reigns supreme—and this year’s, plaid, also happens to be a tried-and-true holiday season classic. Between tartan’s big runway showing this season and TikTok’s obsessed with a “Ralph Lauren Christmas,” it only makes sense to invest in a red, green, or blue plaid dress. Minis are great for parties, especially with trendy tights and metallic heels, while Hill House’s signature Nap dress is a comfortable choice for living room gatherings. But any of these picks will earn you the title of best-dressed guest.
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