10 Winter Dresses for Women Who Want to Look Elegant But Feel Comfortable

10 Winter Dresses for Women

It can be challenging to find the perfect winter dresses that are stylish and keep you warm. When the weather gets really cold, you don’t want to limit yourself to only wearing jeans, pants, leggings, etc. But you also don’t want to feel like you’re freezing in a dress, right? With the right styling tricks, you can wear your favorite dresses in the winter no matter the occasion. Today, we’re sharing TEN winter dresses that you can comfortably wear in the dead of winter. We’re including casual and dressy options as well as some tips on how to add layers to make the looks even warmer for this winter season.

If you’re dealing with cold weather where you live, we have this post on how to layer clothes for cold weather that’s a must-read. Plus, if you need more guidance, you can also check out this post with even more tips on how to wear dresses in winter.

Casual Winter Dresses for Women

#1) Staud Aldrin Cable Knit Layered Sweater Dress

First, let’s talk about some casual winter dress options! This Staud dress is one of those versatile pieces you can dress up or down so we shared two ways to wear it above. It’s actually a twofer dress with the look of a white button-down shirt layered underneath. We love the crisp white collar and shirttail and since it’s built-in, it takes all the guesswork out of layering. On the left, Erin styled it as a dress with suede Stuart Weitzman booties. If you live in a super cold climate, add some tights and throw on your warmest wool coat for a chic and effortless (but warm!) outfit.

On the right, instead of wearing it as a dress, Erin threw on a pair of Frame straight-leg jeans underneath. This is where the more casual look comes in and you’ll have some added warmth too. You could also throw on a gorgeous camel coat or jacket if you’re headed out the door and need extra warmth.

#2) Isabel Marant Étoile Michaela Dress

In this look, Erin’s wearing a chic little black mini dress by Isabel Marant Etoile. It looks almost brown in the photo but it’s actually a really cool faded black. We love the dramatic puff shoulders and super flattering ruching around the tummy. The length is also really flattering for Erin (she’s 5’4” for reference). This dress heavier-weight jersey material that’s pretty warm so you won’t get cold. We love the casual but modern feel of this dress! Erin styled it with some Isabel Marant boots from a few years ago that have a fun western-inspired vibe. You could easily recreate this look with a black sweater dress and black booties you might already have in your closet! For more warmth, throw on a pair of tights and a black coat or jacket.

#3) Callahan Nayeli Dress

For those of you who like to lighten up their winter wardrobe with ivory, creams, and whites like Erin does…this one is for you! Erin’s wearing an ivory sweater dress by Callahan that has the prettiest geometric details throughout. The cinched waist is very flattering. And the turtleneck has loose bunching so it doesn’t feel like it’s too high or too tight of a neck. Erin styled it with a pair of ivory knee-high boots by Schutz. She has these boots in multiple colors and loves them. If you need a pair of knee-high boots for fall/winter, these are the best!

#4) Open Edit Cardigan Dress

This awesome Open Edit cardigan dress has a gorgeous, ribbed texture and the weight of the fabric is perfect if you live in a warmer winter climate or just don’t want such a warm winter dress. It’s not too thin that it shows lumps and bumps, but it’s not so thick that you’ll get too warm. Erin loves the collar and the buttons down the front. You can unbutton a few extra buttons and add a lacy bralette for some extra sexiness on date night. Or keep it buttoned up a little higher if that makes you more comfortable. Oh…and the best part is… it’s only $89! Erin styled it with a pair of black booties and you can throw on your go-to wool winter coat when you’re headed out the door.

See how Erin styled this cardigan dress in multiple ways in this post.

#5) Free People Mont Blanc Cable-Knit Dress

Erin got this cute cable knit dress by Free People last year and it’s so good we had to share it this year too! We love the cable knit details and zip front that make it feel very casual. She styled it with a pair of western-inspired knee-high boots and a teddy coat. If you’re worried about your legs getting cold, you can wear a pair of leggings or tights under the dress. But the taller boots and the big teddy coat really help keep you warm. You could also try a pair of over-the-knee boots too! This dress has limited sizing so we linked some similar options below.

More Formal Winter Dresses for Women

#6) Cinq à Sept Vegan Leather Mckenna Dress

If you’re looking for cute winter dresses that are also a little dressier, the rest of these are for you! First up is this gorgeous Cinq à Sept vegan leather dress. Everything about this dress is SO good…the long sleeves with bell cuffs, the flattering twist front detail, the flattering v-neckline, and the beautiful deep brown color. It’s perfection. If you have a holiday party or just want a fabulous vegan leather dress in your dress rotation, this one is perfect! Erin styled it with patterned tights and some Michael Kors faux leather booties that are so chic and sexy. To complete the look, throw on a long coat and you’re ready for a party, event, or date night.

#7) Steve Madden Lori Knit Dress

This is something you could wear on date night or to the office (with a blazer). Erin’s wearing a black Steve Madden sweater dress that’s so good…and SO affordable (only $99!). The material is thick enough to hide lumps and bumps but not too thick. So, if you run hot or are dealing with hot flashes, this dress still works. We love the one-shoulder neckline that’s very flattering on most body shapes. It has a roomier fit in the waist, which will help hide any tummy concerns you may have. The top almost fits and feels like you’re wearing a chunky sweater. But the bottom half is fitted and flattering. The midi dress length is also lovely. Erin styled the dress with her go-to Stuart Weitzman sock booties that she’s owned for YEARS and wears with pretty much everything.

#8) Staud Hazel Dress

Next up is this cool and unique brown corset dress by Staud. The top of the dress is cotton poplin cotton and the bottom is a chunky ribbed knit. The top has a menswear-inspired feel while the bottom is very sexy and fitted. The fitted bustier bodice and thigh-high slit on the side add to the sexiness of this dress too. It runs true to size and Erin is wearing a small. On her feet, Erin’s wearing a pair of tall brown Schutz boots with a sexy stiletto heel. These are the same boots she’s wearing in #3 but in a gorgeous dark brown suede. We love how the brown boots pair perfectly with the brown dress to keep the line long and lean. For even more warmth, throw on a dark chocolate brown coat to keep the monochrome look going, or try a black coat for an unexpected black-and-brown color combination.

#9) Norma Kamali Asymmetrical Turtleneck Gown

If you’re looking for something even sexier and dressier than the last look, this dress will do the trick! This Norma Kamali dress is super fitted but has strategic ruching that’s SO flattering. We love the drama of the asymmetrical hem. It’s pretty short on one side but the long sleeves, turtleneck, and length on the opposite side offset that so you don’t feel like you’re showing too much skin. Erin styled it with the same knee-high Schutz boots to complete the look. For even more warmth, add tights, throw on a coat, and you’re ready to go!

#10) Remain Birger Christensen Colorblock Dress

This Remain Birger Christensen color-blocked midi dress is so chic and flattering. It’s pretty lightweight, so it’s better for those of you who live in warmer climates. But, it’s thin enough to layer beautifully under blazers, jackets, and coats so you can still get some added warmth. The exact dress is sold out so we linked some similar options below that will be just as flattering. Erin styled it on the right with her go-to Balmain blazer and the same Schutz knee-high boots in black…did we mention how much Erin loved these boots?! She has them in four colors!

Which one of these dresses could you see yourself wearing all winter long? Let us know in the comments below!

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