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The 20 Best Winter Dresses to Wear All Season Long
You don’t have to compromise on style for warmth
The best winter dresses offer a welcome alternative to the usual sweater-and-pants uniform we all fall prey to when the temperatures drop. While wardrobe essentials such as coats, knitwear, and jeans continue to be the mainstays that see us through the coldest months, winter dresses offer the variety we crave. They can be layered with blazers, sweaters, and hosiery. Plus, let’s face it, they make the best styling partner for the leather boots you might have invested in this season as well.
Thanks to the return of the new bohemian movement, some of the best winter dresses also have trend-forward appeal. You’ll find boho-chic dresses like dark floral frocks from Ulla Johnson and Dôen, prairie styles from Sea, and even a long-sleeved chiffon number from J.Crew, for an affordable take, all within our roundup. Naturally, no winter-dress list would be complete without sweater dresses, the perfect combination of warmth and effortless style. We have found plenty of winners, from body-con silhouettes at Staud and Éterne to chunkier turtleneck styles at Guest in Residence and Everlane. And those who favor a polished aesthetic will love our full-skirted, ladylike picks from Self-Portrait and Khaite or a classic mini shift dress from Prada (all of which pair beautifully with all the Mary Janes we have been seeing).
There’s no better time than the present to scoop up these seasonally appropriate buys. Shop the 20 best winter dresses for women below.
Embrace your inner boho with Dôen’s Marybell dress. The dark floral print is inspired by Victorian-era designs, evoking the nostalgic mood the brand is known for. Simply style with a chunky fisherman-style cardigan and knee-high boots for a cute winter look.
Sizes: XXS–XXL
Material: viscose
Norma Kamali’s chocolate-brown dress is a power move. Featuring strong shoulders, a belted waist, and a pleated skirt, its soft yet tough silhouette is perfect for the woman who needs to command the room but knows she doesn’t have to sacrifice her comfort to do so.
Sizes: 2XS–XL
Material: polyester, elastane
Ulla Johnson Amaya Floral Turtleneck Dress
Ulla Johnson knows how to make a good floral dress. Luckily, this maxi version is winterized to face the cold. It features a turtleneck and a long-sleeved body with a full skirt, the ideal silhouette for layering under a black blazer and styling with knee-high boots for a chic office look.
Sizes: XS–XL
Material: rayon, elastane
We love chiffon for the ethereal effect it creates, but on its own it’s not exactly winter-friendly. J.Crew’s ballet dress offers the perfect solution: a fitted bodice crafted from cotton for maximum warmth attached to an ankle-length chiffon skirt for maximum swoosh.
Sizes: 2XS–3X
Material: cotton, elastane
No matter the season, a black dress is always a smart investment for having at the ready. Toteme’s take is ideal for winter, with long sleeves and a draped bodice. It effortlessly goes from day to night with the swap of accessories. Think boots and slingback pumps for the office or a jeweled sandal for a cocktail fete.
Sizes: 2XS–XL
Material: viscose, elastane
Cashmere is without a doubt a luxury, but you can find wonderful pieces that won’t break the bank. Everlane’s midi-length turtleneck dress is made from a blend of recycled and GTS-certified cashmere that’s been combed for maximum softness and superior warmth. But the best part is that it’s available at a price that won’t give you buyer’s remorse.
Sizes: 2Xs–2XL
Material: cashmere
With its split sleeves, elegant drop waist, and full bubble-hem skirt, Simkhai’s monochome dress is the statement piece that can be worn every day.
Sizes: XS–XL
Material: polyester, nylon
The temperatures may be frigid, but the show must go on. Whether you’re the lucky guest at an intimate dinner or have tickets to an upcoming performance, you’ll need an occasion dress. Staud’s floral appliquéd organza dress is the one.
Sizes: XS–XL
Material: polyester, cotton, elastane
Guest in Residence Turtleneck Maxi Sweater Dress
Clad in cashmere from the neck down? We can’t think of anything cozier. Guest in Residence’s maxi dress is the piece you slip on when you want to feel extremely cozy but still look polished.
Sizes: XS–2XL
Material: cashmere
Inject a ladylike feel into your winter wardrobe with this ribbed dress from Self-Portrait. It has a stunning collared neckline and gold-tone buttons, giving it all the right details for a classic touch. Winter chills are no match for this dress’s full skirt and long sleeves.
Sizes: XS–L
Material: viscose, polyester, polyamide, elastane
Invest in a refined dress from an up-and-coming brand that will see you through the next few months. The wool-blend fabrication will be extra warm on those dreary days, while the fitted turtleneck top keeps body heat close and circulating. Pair with pointed pumps, boots, or a sleek slingback for endless appeal.
Sizes: 34–44 FR
Material: virgin wool, nylon, polyamide, elastane
Altuzarra Stunt Midi Sweater Dress
Seeking a boost of style inspiration to break up those winter-wardrobe blues? Altuzarra’s elegant take on the sweater dress is it. The reverse-oriented collar brings a design-forward touch to a minimalist silhouette. Be sure to check out the back for a surprise: It’s open and has special toggle-closure detailing that has become synonymous with the brand.
Sizes: XS–XL
Material: viscose, polyester, polyamide, elastane
Those who live in temperate climates will love the look of Sea’s prairie dress. It still feels wintery enough to wear from December through March, but it’s not as heavy as a wool or cashmere option. Style with a cozy sweater over top when an extra layer is needed.
Sizes: XXS–XL
Material: cotton, viscose
Wool is always a good idea if you are craving something warm to wear. Staud’s Sabrina dress is made from merino wool, and it’s a steal at under $400. We are obsessed with the scoop neckline and midi length, ideal for wearing with your favorite boots and a chunky hoop earring.
Sizes: XS–XL
Material: merino wool
Cinq à Sept Brenton Cosmo Flower Puffed-Sleeve Dress
Winter florals are sure to ward off any signs of seasonal depression. Those who can’t wait for spring’s return can keep the warm feelings top of mind with this printed puffed-sleeve dress. Wear it under a cozy knit with tights when the bitter cold is in full force.
Sizes: 00–16
Material: polyester
Khaite Lisette Turtleneck Sweater Dress
Drop-waist maxi dresses are having a moment, and winter is the perfect time to invest in one. Khaite’s fitted style is made from a wool-blend fabrication, designed to withstand the toughest conditions. Wool is a naturally insulating fiber and has moisture-wicking properties while also being breathable and odor-resistant, so you will be covered from all points.
Sizes: XS–L
Material: wool, polyamide, polyurethane
Éterne Long-Sleeve Turtleneck Maxi Dress
Simplicity is key when investing in the best wardrobe building blocks. Just like a black turtleneck, the dress version is essential during the winter months. We love how soft and silky this maxi dress from Éterne feels. Pair it with boots, ballerina flats, or pumps all season long. It’s also supermodel-approved.
Sizes: XS–XL
Material: cotton, modal, spandex
Winter whites (in this case, ecru) are always a reliable color palette to wear this time of year. We can’t wait to wear this A-line minidress with black hosiery and a Mary Jane shoe for festive gatherings and more. For a sartorial spin, try wearing it as a tunic over trouser pants.
Sizes: 36–50 IT
Material: viscose
Proenza Schouler Athena Rib Maxi Dress
Make an entrance with this ribbed-knit maxi dress from Proenza Schouler. It’s sleek, it’s chic, and it’s made from the softest rib fabric, which will keep you comfortable all day. Throw a lightweight, skinny scarf on for a cute styling touch.
Sizes: XS–XL
Material: viscose, polyamide, silk
Maximalists and minimalists will find their best match in this slinky dress from By Malene Birger. We imagine styling it with a blazer and slingback heels for the office, with an organic-shaped earring for modern edge. Naturally, it also works with knee-high boots and a tailored wool coat.
Sizes: 32–44 DK
Material: viscose, silk
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