21 Winter Dresses That Go With Tights, Boots, and Sneakers—Because Nobody Wants To Freeze at the Holiday Party
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
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!
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).
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.
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
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.
Looking to stay warm but also show a little leg (or boot)? This cozy sweater dress keeps you protected from the winter chill while also featuring a high slit that is perfect to show off all of your new Black Friday shoes. The cotton material is supremely soft, and the body con to flare fit hugs in all the right places.
Known for their nap dresses, Hill House Home has become a staple when it comes to cozy apparel that still looks supremely stylish. This velvet dress will keep you warm while also being the perfect go-between dress when you have a holiday dinner in the evening, then a Hallmark movie marathon after.
Bring a pop of pattern to your winter wardrobe with this fun, floral midi dress. It’s warmer than a mini, but also not so long that you can’t see your cute boots. As a bonus, the dress is also eco-friendly, since it’s made from recycled polyester.
Best winter dresses for layering
Silk slip dresses are the answer to all of your layering woes. This eggplant number is perfect to pair with a chunky knit and coat when you’re braving the cold, but also won’t have you dripping in sweat when you get inside.
This cotton, jersey dress may look simple at first glance, but the shoulder cut outs are the moment. The material is so buttery soft that you’ll have no risk of itching if you pair a big wooly cardigan over it. The relaxed fit also makes it perfect for lounging.
Grey winter weather does not mean that you have to wear neutrals all season long. This bright dress is a statement to wear alone, but is also thin enough that you won’t feel like the Michelin Man when you pack on a few layers over it. The nylon material means that it’s also perfectly stretchy so you can actually walk while you wear it.
We love a one-shoulder moment. This long dress can go from day to night with just a few accessory swaps. Pair it with heels for a dinner out or tights and sneakers under a puffer when you’re on the go. The unlined viscose material also feels so smooth on.
Short winter dresses
Winter dresses don’t have to go all the way to the floor to be seasonally appropriate. This velvet mini is festive and is the perfect length to pair with some sparkly stockings.
Business casual never fails. This shirt dress has long sleeves for warmth, a belt that cinches at the waist, and is the perfect length to pair with skinny jeans or leggings when it’s bitterly cold or tights during a fall day. The unlined polyester fabric also feels slinky and chic making it great for a night out.
Sometimes you’re just looking for something that hugs your curves. I mean, who doesn’t love a hug? This ribbed long sleeved body con number is perfect for layering, wearing alone, or pairing with a button down shirt on top so it moonlights as a skirt. It’s also made from a recycled nylon blend so it’s eco-conscious too!
While shimmery anything isn’t limited to the holiday season, cold winter days often call for an extra pop of sparkle. Pair this mini dress with some tall boots for the perfect holiday party look. The V-neck and faux wrap style is versatile and shows just the right amount of skin.
Long winter dresses
Taylor Swift brought cottagecore back, and now it’s not going anywhere. This flow-y number is comfy enough to nap in, but also perfect for a winter frolic through the snow. It’s also made from 100 percent woven organic cotton and features a hand painted design that is sure to steal the show.
This pink dress feels like summer while still being long sleeved and long enough to keep you warm. Make a statement when you walk into any room and pair this collared dress with chunky earrings for an extra flair. The viscose and nylon blend is breathable and stretchy enough to strut in.
This flow-y maxi is festive, fun, and has a fit that’s relaxed enough to leave your legs feeling free (for dancing of course). Also, what says “I’m on my way to a chic winter dinner party” better than velvet? FYI: This is what our commerce editor will be wearing to the Well+Good holiday dinner (she bought it because A. green velvet!, B. it’s long and the material is thick, and C. it makes her feel like a winter wonderland princess).
No, T-shirt dresses don’t have to be short. This cashmere T-shirt dress is comfortable enough to curl up on the couch in, but also flattering enough to wear to dinner.
Simple, a little Morticia Addams, and stretchy to boot, this long-sleeved rib dress is truly a blank slate for the holidays. Dress it up with some shiny jewelry and/or bright boots. Wear it with a teddy. Lean into the all-black look with a black peacoat and black tights. Made of a rayon-elastane blend, this dress is soft and provides warmth in the colder months.
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