The 30 Best Winter Dresses for Every Occasion This Season  (2024)

If you purchase an independently reviewed product or service through a link on our website, WWD may receive an affiliate commission.

Dresses may be synonymous with summertime, but the best winter dresses have just as much ease and styling versatility — even on the coldest days. From fall dresses that can be worn in the winter and chunky knit sweater dresses that don’t sacrifice style for comfort to slip dresses you can layer underneath your favorite sweaters and blazers, there’s a winter dress for every cold weather occasion. And if the party circuit has found its way back onto your calendar this season, there are plenty of festive, winter-friendly co*cktail dresses veering from classic little black dresses to feathers, sequins, and sexy cutouts to choose from, too.

Whether you have a winter affair on your calendar or are looking for a fashionable gift for a woman in your life, keep reading for all the best winter dresses, top trends, and expert styling tips to try this season.

Simon Miller Long-Sleeve Sweater Dress

Best Striped Sweater Winter Dress

Looking to brighten up your winter? Nordstrom Fashion Editor Kate Bellman recommends this colorful striped sweater dress by Simon Miller. Featuring long, slightly flared sleeves and a midi hemline, the ultra-soft sweater dress can easily be dressed up or down—and is guaranteed to add a splash of color to your predominantly black winter wardrobe. As for styling, Bellman says the key lies in the boots. “A tailored knee-high boot moves this cozy style into office relevance, or a heavy lug sole for a casual dinner out,” Bellman recommends.

Simon Miller Long-Sleeve Sweater Dress$325$195Buy Now AT SAKS FIFTH AVENUE

Simon Miller Long-Sleeve Sweater Dress$325Buy Now AT SIMON MILLER

SKIMS Soft Lounge Long-Sleeve Dress

Best Winter Maxi Dress

It should be no surprise that Kim Kardashian’s SKIMS has mastered the art of the comfortable, body-hugging dress that shows off all your curves. This long-sleeve dress has gone viral several times on TikTok, and for a good reason. It’s loved for its ultra-soft fabric, simple design accentuating the body in all the right places, and signature SKIMS neutrals, including black, brown, camel, white, and heather gray. Though comfortable, it should be noted this is a tighter-fitting dress. If that’s not your thing, you can always layer a jacket or sweater on top to get added comfort and style.

What reviewers say: “The softest, most figure hugging lounge dress you will ever come across. The material glides across your skin while you move. 10/10!”

SKIMS Soft Lounge Long-Sleeve Dress$88Buy Now AT NORDSTROM

SKIMS Soft Lounge Long-Sleeve Dress$88Buy Now AT SKIMS

Anine Bing Mika Midi Dress

Best Shirt Dress for Winter

Anine Bing has all the cool girl-approved essentials to build your perfect capsule wardrobe, and this classic shirt dress is a perfect example. The cotton/poplin fabric is crisp with a tailored look and is pretty wrinkle-resistant, making it a great style for winter layering. Style a sweater vest over it for a preppy look, or layer a menswear-inspired blazer over it and add loafers with thick socks. Like a classic white button-down shirt, there are a million ways to style this dress — making it a smart wardrobe investment you can wear all year round.

Anine Bing Mika Midi Dress$300Buy Now AT LUISAVIAROMA

Peter Dundas Cutout Dress

Best Cutout Winter Party Dress

A little black dress will never go out of style, but this cutout design by Peter Dundas puts a twist on the tried-and-true classic. Featuring a skin-bearing cutout across the chest, the long-sleeved LBD is a sexy yet streamlined winter co*cktail dress. Style it with tights and boots or strappy heels to round out the look for night events. And if you’re looking for a statement-making accessory to take the look to the next level, look no further than the Peter Dundas xGrey Goose Martini Bag (which is adorned in Swarovski crystals, by the way).

Peter Dundas Cutout Dress$595Buy Now AT AMAZON

Open Edit Drape Knit Bodycon Dress

You can’t go wrong with a simple little black dress. Yes, it’s a timeless classic, but it’s anything but boring. This draped bodycon style hits just above the knee so that you can wear it with tights or bare legs. The ruched fabric and cut lend a flattering fit that accentuates your figure in all the right places. Keep it minimal, or pair it with statement accessories such as a chunky choker to add flair. If you’re not a fan of the body-hugging fit, you can always layer an oversized blazer on top.

What reviewers say: “I love this dress! Fits perfectly and I got a lot of compliments. Would get it in another color.”

Open Edit Drape Knit Bodycon Dress$79Buy Now AT NORDSTROM

Autumn Cashmere Wrap Dress

Few winter dresses are as cozy as a cashmere dress, and this Autumn Cashmere style checks all the boxes. With a classic wrap design, the gray dress features a wrap tie at the waist but is a classic pullover dress with no closure (so you don’t have to worry about the wrap coming untied throughout the day). The midi length is perfect for pairing with knee-high boots and versatile enough to wear to work, weekend plans, or for a night out to dinner. Plus, the lightweight cashmere fabric is easy to style underneath your winter coat without feeling too bunchy or frumpy.

Autumn Cashmere Wrap Dress$385Buy Now AT SHOPBOP

ASOS Design Edition Feather Dress

Best Festive co*cktail Party Dress

Whether you’re headed to a New Year’s Eve party, a black tie, or a co*cktail event, lean into the more is more attitude this season with this feathered party dress by ASOS. Nordstrom’s Kate Bellman recommends this style as one of the biggest statement-makers of the season thanks to its feather and sequin detailing. And with a dress this bold, you can keep accessories to a minimum to let the outfit do all the talking. Bellman suggests going for a naked, strappy sandal (which you can wear with or without tights) to let this one shine on its own. Style a menswear-inspired blazer or coat over the top and minimalist jewelry for the perfect finishing touch.

What reviewers say: “This dress is beautiful! I truly love it but am still indecisive on whether it is worth keeping. I initially bought to wear for a New Years wedding, but the straps are too long so they will need to be altered. It’s also really heavy on the thin straps, I’m afraid my shoulders might be raw. But I still love the look!”

Asos Design Edition Feather Dress$234Buy Now AT NORDSTROM

Free People Oasis Maxi Dress

Best Boho Winter Dress

If you’re going for more of a boho dress look, Free People is always a failsafe choice. Doing what the brand does best, this long-sleeve maxi dress taps into ‘70s-inspired, laidback ease with billowed sleeves, ruffles, and a floral print. The square neckline is flattering, feminine, and easy to showcase layered necklaces and accessories. This versatile long dress is easy to dress up or down — whether for a casual day or dinner out.

Free People Oasis Maxi Dress$168Buy Now at nordstrom

Proenza Schouler Drop Waist Faux Leather Dress

Best Leather Winter Dress

Leather jackets may be one of your winter go-to’s, so why not try a leather dress? Designers like Proenza Schouler and Jonathan Simkhai experimented with the look on the Fall 2022 runways with feminine silhouettes, from pleated styles to drop waist cuts and cutout shirt dresses. This drop waist style from Proenza is perfect for layering over a crisp button-down shirt or sweater r or wearing on its own underneath a blazer or jacket for an evening look. The leather offers a medium stretch, making winter layering a breeze.

Proenza Schouler Drop Waist Faux Leather Dress$695Buy Now AT SHOPBOP

Anrabess Turtleneck Sweater Dress

Most Budget-Friendly Amazon Winter Dress

Look no further than this top-rated Amazon favorite for an easy, cozy, and everyday sweater dress that won’t break the bank. Available in a range of colors, from muted neutrals to bright blue, the above-the-knee sweater dress features a loose, relaxed silhouette that’s casual and easy to style. Pair it with tights and boots, and layer a jacket or blazer over the top to dress it up, or keep it more casual and comfy with leggings and boots or sneakers. Reviewers love the comfortable fabric and oversized cut that doesn’t cling to the body.

What reviewers say: “I am usually a medium, but could have probably went with a small if I wanted it more fitting. However, this fits me as shown in the pictures and that is what I was looking for. It is not form fitting, but not too baggy either. The material is very soft and cozy. The turtle neck part seems a little bigger on my than in the pictures, but still very comfortable. I got this more for a cozy yet, dressy look and am happy with it for sure!”

Anrabess Turtleneck Sweater Dress$43.99Buy Now AT AMAZON

Reformation Remi Floral Long Sleeve Minidress

Best Long-Sleeve Mini Winter Dress

Reformation is always a go-to for feminine floral dresses you can wear year-round. This romantic style is for you if you’re looking for a mini dress that brings on a playful print. The sweetheart neckline and slightly flared skirt offer a touch of light romance that’s often hard to find when finding winter-friendly dresses. And if you prefer a midi length, the brand offers this style in a longer version too.

What reviewers say: “The cut of the dress is romantic and sexy. It’s snug at the waist then flares out slightly. I don’t like showing my chest, but the sweetheart neckline was pretty modest. The tie at the back adds detail and keeps the sleeves from falling off my shoulders. The dress is a cream color with muted roses true to the color shown on the item pictures. The dress ended at mid-thigh, so it’s definitely a mini-dress.”

Reformation Remi Floral Long Sleeve Minidress$218Buy Now at reformation

Staud Etta Dress

Best Winter Feather Dress

Why not wear a feathered little black dress to all your events this winter? Equal parts fun and classic, feather dresses are having a moment for holiday party style and beyond. Staud’s feathered LBD iteration features a mid-weight knit and ostrich feather trim across the chest and hemline for added flair. Style it with sparkly, over-the-top rhinestone earrings to amp up the drama for more glam. And even though feathers may be trending right now, it’s a detail you can keep in your closet forever to pull out on those special occasions.

Staud Etta Dress$395Buy Now at shopbop

Staud Etta Dress$395Buy Now at mytheresa

Staud Etta Dress$395Buy Now at net-a-porter

Banana Republic Colletta Off-Shoulder Midi Dress

An off-the-shoulder neckline is a quick way to elevate any sweater dress — whether for the office, date night, or an event. This streamlined midi style from Banana Republic is available in two neutral hues that’ll lend that effortlessly chic look and pair perfectly with all your winter coats. Reviewers love that the soft wool blend makes it extremely comfortable, but the elegant silhouette is still flattering, thanks to its side slit and cinched waist detailing. Pair it with tailored boots or strappy heels for a night out.

What reviewers say: “Very flattering neckline and waistline. Super soft material and comfortable! Definite staple.”

Banana Republic Colletta Off-Shoulder Midi Dress$230$189.97Buy Now AT BANANA REPUBLIC

Paco Rabanne Striped Luxe Long Dress

As Nordstrom’s Kate Bellman says, this season is all about technicolor maximalism when dressing up. This two-tone Paco Rabanne number is done in a shiny luxe fabric that takes its red and lavender stripes up a notch. For an unconventional night look, this high-neck, maxi dress style is easy to pair with heels or boots — and feels like an unexpected pick. You could even style it with chunky combat boots for an edgy contrast.

Paco Rabanne Striped Luxe Long Dress$1190Buy Now AT LUISAVIAROMA

Everlane Cozy Stretch Turtleneck Dress

Best Winter Turtleneck Sweater Dress

A simple turtleneck sweater dress is a staple in any winter wardrobe. This classic design by Everlane is soft and offers a slightly oversized fit that ensures you’re comfortable without feeling too casual or frumpy. Reviewers love that the cozy fabric doesn’t cling — making it easy to wear on its own or layered underneath a coat or jacket. The above-the-knee hemline is ideal for styling with tights, boots, socks, and loafers. The sustainably-sourced fabric consists of animal-friendly wool and yak hair blended with recycled nylon and elastane.

What reviewers say: “Slightly oversized fit as intended but not sloppy; very flattering! Soft and warm. The bit of stretch helps the garment maintain its shape. Can be styled so many ways! I wish it came in more colors! Will be on constant repeat in my fall/winter wardrobe.”

Everlane Cozy Stretch Turtleneck Dress$148Buy Now AT EVERLANE

Simon Miller Space Dress

Best Casual Cutout Winter Dress

The cutout dress trend is perfect for those looking for casual winter dresses and formal winter dresses. The subtle asymmetric collarbone slit on this Simon Miller maxi dress is unique enough to make a statement without feeling like it’s too much for daytime wear. The long hem allows one to effortlessly style it with any boots — whether you want to make it more casual with a lug sole boot or sleeker with a tailored heel. The knit is mid-weight, so it’ll keep you warm without feeling too heavy or frumpy underneath your coat.

Simon Miller Space Dress$206.50Buy Now AT SHOPBOP

Simon Miller Space Dress$295Buy Now AT NORDSTROM

Simon Miller Space Dress$295$206.50Buy Now AT BLOOMINGDALES

Loulou Studio Striped Midi Dress

Best Cable Knit Winter Dress

Nothing says cozy like a chunky cable knit dress, and this style from Loulou Studio puts a luxe twist on the look. Made from a merino wool and cashmere blend, the soft dress offers contrasting stripes and textured details that let it stand out from your typical sweater dress. The turtleneck design ensures maximal warmth, and the slits provide more ease of movement. Pair it with cozy clogs and a designer crossbody bag for brunch with friends.

Loulou Studio Striped Midi Dress$560Buy Now AT NET-A-PORTER

ASTR The Label Sweater Dress

Who says sweater dresses can’t be sexy? Reviewers love this cutout ASTR The Label sweater dress for its comfortable body-hugging material that offers a nice weight to keep you warm and simultaneously holds you in. The twisted cutout neckline adds some unexpected edge to a style that’s perfect for going out to dinner or can be dressed up further for party attire. The long sleeves and midi length balance out the cutouts and slit, so you can style it for several occasions.

What reviewers say: “Heavy material and such great quality. Its classy and sexy all at same time. It has stretch to it and fits body perfect.”

ASTR The Label Sweater Dress$89Buy Now at nordstrom

Staud Shoko Sweater Dress

Staud’s two-tone cardigan sweater dress has been a timeless favorite for a good reason. The ribbed knit and elongated length is a flattering choice that can be worn as a dress when buttoned or as a cardigan when left open. The brand offers the bestseller in a range of two-tone colors, so there’s something for everyone’s style. And with its straight silhouette, it’s easy to pair with sneakers, loafers, or boots without giving it much thought. Some reviews note it runs slightly big, so if you want a tighter fit, you may want to size down.

Staud Shoko Sweater Dress$165Buy Now at amazon

Staud Shoko Sweater Dress$165Buy Now AT SHOPBOP

Whitney Morgan Cashmere-Wool Midi Dress

Best Overall Plus-Size Winter Dress

A newly-launched, woman-owned brand to watch, Whitney Morgan specializes in luxury fashion for plus-size women. The brand’s midi sweater dress, made of soft cashmere and wool, features a slightly oversized fit that still offers an elegant, tailored look. The V-neck, long-sleeve style is versatile enough to dress up or down, whether you’re looking for a work dress or something to wear on the weekend. Just add knee-high boots and a shoulder bag, and you’re ready to go. The brand’s pieces are available in 1X, 2X, and 3X (the equivalents of sizes 14-24).

Whitney Morgan Cashmere-Wool Midi Dress$395Buy Now at neiman marcus

Jonathan Simkhai Wrap Blazer Dress

Best Winter Blazer Dress

Jonathan Simkhai breathes new life into the classic little black blazer dress with this wrap style. Offering very subtle waist cutouts and a sculptural gold clasp, this dress may be classic; however, it’s anything but basic. If you’re looking to upgrade your co*cktail dress collection, this cutout style feels of the moment without being too trendy that you won’t wear it again for seasons to come. The above-the-knee style also featured two front pockets and notched lapels.

Jonathan Simkhai Wrap Blazer Dress$695Buy Now at farfetch

Rixo Velvet Sequin Mini Dress

Best Pink Winter Dress

The Barbiecore trend isn’t slowing down anytime soon, and there’s no better time to try it than now. This hot pink minidress adorned in velvet and sequins is a perfect way to make a splash on the winter party circuit. The ‘60s-inspired style features blouson sleeves, an open back with a velvet bow tie, and a high neck. Pair it with simple hoop earrings and nude or black heels.

Rixo Velvet Sequin Mini Dress$445Buy Now AT NET-A-PORTER

Tanya Taylor Marla Dress

Winter party style doesn’t always have to include sequins and feathers. This maxi dress by Tanya Taylor gives understated glam with an off-the-shoulder sweetheart neckline and ultra-flattering ruching. Featuring a thigh-high slit, you could style it several ways for any kind of special event — whether you wanted to keep it minimal with strappy heels, add a sleek pointed ankle boot, or create a contrast with a chunky lug sole boot. Plus, the rich chocolate hue is a nice way to venture away from your go-to black while still feeling neutral. Since it has a strapless design, we recommend wearing it with a strapless bra.

Tanya Taylor Marla Dress$575$345Buy Now at shopbop

Vince Satin Slip Dress

There’s nothing more classic than a simple, ‘90s-inspired slip dress — and yes, you can wear them all winter long too. The versatile design is easy to layer underneath all your favorite chunky knit sweaters for daytime or office-friendly looks. Or, you can layer it over a lace bralette and underneath a blazer for a nighttime look that’s timeless and sexy.

What reviewers say: “This is such a beautiful, classic dress. The fit is very flattering. It can be dressed up or down, from elegant to casual with a sweater or tee. Love it.”

Vince Satin Slip Dress$325Buy Now at bloomingdales

Vince Satin Slip Dress$325Buy Now at vince

& Other Stories Mock Neck Ribbed Dress

Bestp Winter Sweater Dress

Made of recycled wool, the relaxed fit of makes it both comfortable and flattering. Available in green, gray, or beige, the cozy style features a mock neckline that offers higher coverage. The side slits give it a relaxed shape and allow for movement. Style it with tights and boots, and enjoy that the mid-weight fabric will keep you warm without feeling too bulky when worn underneath your winter coat.

J.Crew Oliphant Shirt-Waisted Maxi Dress

The J.Crew revival is in full force, thanks to the brand’s stylish new head of women’s design, Olympia Gayot. For a day-to-night dress that feels like a fresh change from your typical winter wardrobe, opt for this floral maxi dress. The colorful print is a standout, and the cut will make you feel (and look) instantly polished for any occasion. Style it with pumps for the office, a weekend brunch, or a special occasion.

J.Crew Oliphant Shirt-Waisted Maxi Dress$398$288Buy Now AT J.CREW

Hill House Home Velvet Nap Dress

Best Velvet Winter Dress

Yes, you may know the original nap dress, but have you tried a velvet nap dress? Hill House Home’s latest iteration is a rich, velvet fabric that takes the entire look up a notch for party style. Whether you wear it on its own or layer it over a turtleneck, this tiered silhouette will make a statement. And, if velvet isn’t your thing, the brand offers a range of other textured fabrics.

What reviewers say: “I am shocked. This dress is super flattering and the straps are just magnificent!!! They stay up and make the dress feel elegant and regal. Definitely a must-buy!! I love how you can dress it up or down!! Also, you can wear a bra with straps because it gets covered by the straps of the dress. Very impressed.”

Hill House Home Velvet Nap Dress$150$99Buy Now AT HILL HOUSE HOME

Abacaxi Winter Turtleneck Dress

Founded by South Asian-American designer Sheena Sood, Abacaxi is a small brand inspired by the cultures and textiles of India. This maxi turtleneck dress is hand-dyed by dyers in New Delhi, India, and features a pink and white tie dye design. Its thick rib knit fabric is flattering and designed to keep you warm while hugging the body. Details like a flared ruffle hem and extra-long sleeves with armholes make this style a coveted standout.

Abacaxi Winter Turtleneck Dress$325Buy Now AT ABACAXI

The Line By K Cali Dress

Small brand The Line By K is known for its minimal designs that subtly merge comfort with sensuality, and this long-sleeve maxi dress is proof of that. Maxi dresses are having a moment, and this sleek full-coverage iteration is perfect for test-driving that trend in the winter. The stretchy dress is comfortable and sleek, featuring a plunging neckline and ruched paneling to accentuate the waist. Ideal for date night or weekend plans, pair this style with chunky combat boots for a ‘90s-inspired look.

The Line By K Cali Dress$179Buy Now THE LINE BY K

Henning Ribbed Knit Dress

Best Plus-Size Winter Work Dress

New York-based brand Henning is known for its timeless, tailored pieces for plus-size women. Perhaps one of the brand’s staple styles, this ribbed knit dress is a wardrobe essential and workwear must-have. The boat neckline is elegant and pairs perfectly underneath the brand’s menswear-inspired blazers and jackets. As a bonus, the stretchy, mid-weight fabric is made of moisture-wicking fabric, so you won’t sweat underneath all the winter layers. A wardrobe investment you’re sure to wear a million ways for years to come.

What reviewers say: “Love this knit dress, and I’ve never loved a knit dress before! It’s thick but not heavy — clearly designed very thoughtfully with a higher, in-style neckline and a longer midi length. I’ve been wearing it to work and out to dinner after because it’s super versatile. Highly recommend!”

Henning Ribbed Knit Dress$289Buy Now AT HENNING NYC

Meet the Expert

Kate Bellman is the Senior Managing Fashion Editor at Nordstrom, where she oversees the top fashion trends, designers, and key pieces of the season.She’s a fashion industry executive with 20+ years of multi-faceted management experience acquired in top brands such as Anthropologie andKateSpade as well.

Meet the Author

Lauren Alexis Fisheris an editor, writer, and consultant with over eight years of experience in thefashionindustry. After spending six years as a digital market editor at Harper’s Bazaar and a lifetime scrolling the internet, she’s well-versed in shopping all the best trends and pieces online — from winter dresses to cold-weather essentials and beyond.