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21 Winter Dresses That Go With Tights, Boots, and Sneakers—Because Nobody Wants To Freeze at the Holiday Party

winter dresses

Photo: Getty Images/F.J. Jimenez

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Most of us can agree that winter is for bulky sweaters and fleece-lined everything (like these fleece-lined leggings we love so). But there are a few occasions during the cold months that may call for a winter dress (a holiday party, family gathering, special date night out, or just feeling glam on your couch—because why not), and it can be tricky finding one that’s comfortable and either long, or goes well with some warm tights. Luckily, there’s a wide variety of flow-y and/or tights-compatible dresses that are cold weather-approved that you can wear until the sunshine decides to reemerge (and you’re counting down the days just like we are, we know).

Just like your summer and spring collection, winter dresses come in every shape, style, color, and cut, and they come in a whole range of prices, so there is sure to be an option for every event you have in your diary, budget, and loving giftee on your list. Whether you opt for short, long, or in-between, they’re made for pairing with boots (or sneakers), are versatile beyond belief, and look just plain cool (while keeping you warm). Scroll down to shop the best winter dresses that you’ll want to add to your cold weather wardrobe now and always.

Best holiday party winter dresses



Petal & Pup Folger Dress — $70.00

Nothing says the holiday season like the color red. This flow-y slip dress is striking, versatile, and will have heads turning when you walk in the room. Bonus points because the silky material feels great on your skin!



NIA Alexandra Dress — $88.00

If you’re looking for a shorter number, this silky LBD is the perfect pick. The halter back and front cut out make it different from the other black dresses in your closet, and it’s versatile enough to be paired with tights in the winter (or wear it alone in the warmer months).



Nana Jacqueline Quin Blazer Dress — $485.00

Channel your inner Jackie O with this sleek, short blazer dress. It gives us maximum class and sophistication while still having long sleeves to keep you warm. The mid-length style is also perfect to pair with heels for legs that look 10,000 miles long.



Into The Night Drop Bow Dress — $180.00

We love a cut-out. This sparkly dress is perfect for holiday parties and to ring in the New Year, has long sleeves to keep you warm, but also has exposed shoulders to show a saucy peek of skin. The nylon and spandex material is also stretchy, so it has prime mobility for hitting the dance floor.

Warmest winter dresses



Falconeri Pleated Wool Dress — $527.00

What’s warmer than wool? This long woolen A-line dress is thick and heavy to keep you toasty and protect you from the wind, while also featuring detailed pleats that elevate the style.

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