21 best winter dresses for every occasion in 2021

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Most of us can agree that winter is for bulky sweaters and anything fleece lined (like those fleece lined leggings we love so much). But there are a few occasions during the cold months that may require a winter dress (a holiday party, a family reunion, a special night out, or just feeling glamorous on your couch – because why not), and it can. be difficult to find one that is comfortable and either long, or goes well with warm tights. Fortunately, there is a wide variety of flowy and / or tights compatible dresses that are cold weather approved that you can wear until the sun decides to reappear (and you count the days like us, we know). .

Just like your summer and spring collection, winter dresses come in all shapes, styles, colors and fits, and they come in a whole range of prices, so there will definitely be an option for every event you have on your planner, budget, and loving gift on your list. Whether you opt for short, long, or mid-length shoes, they are designed to pair with boots (or sneakers), are versatile beyond imaginable, and look just plain cool (while keeping you in the hot). Scroll down to shop for the best winter dresses that you will want to add to your cold weather wardrobe now and always.

Best winter dresses for the holiday season

Petal & Pup Folger Dress – $ 70.00

Nothing says the holiday season like the color red. This flowy slip-on dress is striking, versatile, and will turn heads as you step into the room. Bonus points because the silky material is pleasant on the skin!

Alexandra NIA Dress – $ 88.00

If you are looking for a shorter number, this silky LBD is the perfect choice. The open back and front cutout make it different from other black dresses in your wardrobe, and it’s versatile enough to pair with tights in the winter (or wear it on its own in the warmer months).

White dress

Nana Jacqueline Quin blazer dress – $ 485.00

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

Knot Night Dress – $ 180.00

We love a cutout. This sparkly dress is perfect for the holiday season and to celebrate the New Year, has long sleeves to keep you warm, but also has exposed shoulders to show a sassy peek on the skin. The nylon and spandex material is also stretchy, giving it optimal mobility to hit the dance floor.

The warmest winter dresses

Falconeri Pleated Wool Dress – $ 527.00

What could be warmer than wool? This long wool A-line dress is chunky and heavy to keep you warm and shielded from the wind, while featuring detailed pleats that enhance the style.

ASTR the Label Long Sleeve Split Midi Sweater Dress – $ 79.00

Want to stay warm but also to show off a little leg (or a boot)? This comfy sweater dress protects you from the winter cold while featuring a high slit that’s perfect for showing off all your new Black Friday shoes. The cotton material is extremely soft and the flared body conforms perfectly to the shapes.

Hill House Home The Ellie Nap Dress – $ 175.00

Known for its nap dresses, Hill House Home has become a staple when it comes to comfy clothes that always look extremely stylish. This velor dress will keep you warm while being the perfect in-between when you have a holiday dinner in the evening, and then a Hallmark Movie Marathon afterwards.

Verity Nanushka Dress – $ 395.00

Bring a pop of pattern to your winter wardrobe with this fun floral midi dress. It’s hotter 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 is made from recycled polyester.

Best winter dresses to layer

Verona Babydoll Dress Rebecca Minkoff – $ 298.00

Silk evening dresses are the answer to all your layering problems. This eggplant number is perfect to pair with a chunky knit and a coat when you brave the cold, but it also won’t make you run into a sweat when you step inside.

Bassike cutout cotton-jersey midi dress – $ 260.00

This cotton jersey dress may seem simple at first glance, but the cutouts at the shoulders are the moment. The material is so soft as butter that you won’t have any risk of itching if you wear a chunky wool cardigan over it. The relaxed fit also makes it perfect for lounging.

Simon Miller Xema Dress – $ 198.00

The gray weather of winter doesn’t mean you have to wear neutrals all season. This shiny dress is a statement to wear on its own, but it’s also sheer enough that you don’t feel like the Michelin man when you put a few layers on it. The nylon material means it’s also perfectly stretchy so you can actually walk while you’re wearing it.

Gaia Zora Cult Dress – $ 418.00

We love a one-shoulder moment. This long dress can be worn from day to night with just a few exchanges of accessories. Pair it with heels for dinner or with tights and sneakers under a puffer jacket when you’re on the go. The unlined viscose material also feels so slowly.

Short winter dresses

Norma Kamali NK Tie Front Mini Shirt Dress – $ 165.00

Business casual is never lacking. This shirt dress has long sleeves for extra warmth, a belt that tightens at the waist and is the perfect length to pair with skinny jeans or leggings on a really cold day or tights on a fall day. The unlined polyester fabric is also form-fitting and chic, making it ideal for a night out.

Maria McManus Recycled Nylon Blend Long Sleeve Bodycon Mini Dress – $ 590.00

Sometimes you’re just looking for something that hugs your curves. I mean, who doesn’t love hugs? This ribbed, long-sleeved body number is perfect to layer, wear on its own, or pair with a button-up shirt to make it moonlit like a skirt. It’s also made from a recycled nylon blend, so it’s eco-friendly too!

Justina Tanya Taylor Dress – $ 525.00

While all that glitters isn’t limited to the holiday season, cold winter days often call for an extra touch of sparkle. Pair this mini dress with tall boots for the perfect holiday look. The V-neck and wrap-over style are versatile and show just the right amount of skin.

Long winter dresses

WVN Chester Dress – $ 288.00

Taylor Swift brought the cottagecore back, and now it’s not going anywhere. This flowing number is comfortable enough for a nap, but also perfect for frolic in the winter in the snow. It’s also made from 100% organic woven cotton and features a hand-painted design that’s sure to steal the show.

Hanifa Soraya Maxi – $ 289.00

This pink dress looks like summer while being long sleeved and long enough to keep you warm. Make a statement as you walk into any room and pair this collar dress with chunky hoop earrings for an extra touch. The viscose-nylon blend is breathable and stretchy enough to strut around.

Anthropologie Long Puff Sleeve Velvet Dress – $ 230.00

This flowing maxi is festive, fun, and has a cut relaxed enough to leave your legs free (for dancing of course). Also, what says better than the velvet “I’m on my way to a chic winter dinner”? FYI: this is what our business writer will be wearing for 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 she is in a winter wonderland Princess).

big eros

The Great Eros Stella Long Sleeve Ribbed Dress – $ 315.00

Simple, a little Morticia Addams and stretchy to boot, this long sleeve ribbed dress is truly a blank slate for the holidays. Dress him up with shiny jewelry and / or shiny boots. Wear it with a plush. Channel the all-black look with a black pea coat and black tights. Made from a blend of rayon and elastane, this dress is soft and provides warmth in the colder months.

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