The 30 Best Winter Dresses for Every Occasion This Season

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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 cocktail 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.

Top Winter Dresses for 2022 & 2023

Simon Miller Long-Sleeve Sweater Dress

Best Striped Sweater Winter Dress

Sizes: XS-XL
Fabric: 62% acrylic, 28% polyester, 7% wool, 3% Lycra spandex
Care: Machine wash, dry flat

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~~  $195 Buy Now AT SAKS FIFTH AVENUE

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

SKIMS Soft Lounge Long-Sleeve Dress

Best Winter Maxi Dress

Colorways: Brown, black, camel, wine, white, heather gray 
Sizes: XXS-4X
Fabric: 91% modal, 9% spandex
Care: Machine wash, tumble dry

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 $88 Buy Now AT NORDSTROM

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

Anine Bing Mika Midi Dress

Best Shirt Dress for Winter

Sizes: XS-L
Fabric: 100% Cotton
Care: Hand wash cold or dry clean

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 $300 Buy Now AT LUISAVIAROMA

Anine Bing Mika Midi Dress $300 Buy Now AT FARFETCH

Peter Dundas Cutout Dress

Best Cutout Winter Party Dress

aSizes: 0-8
Fabric: 85% Viscose, 11% Polyacrylic, 4% Elastane
Care: Dry clean

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 cocktail 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 x Grey Goose Martini Bag (which is adorned in Swarovski crystals, by the way).

Peter Dundas Cutout Dress $595 Buy Now AT AMAZON

Open Edit Drape Knit Bodycon Dress

Colorways: black and orange
Sizes: XXS-XL 
Fabric: 95% polyester, 5% spandex
Care: Machine wash, lay flat to dry

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 $79 Buy Now AT NORDSTROM

Autumn Cashmere Wrap Dress

Sizes: S-XL
Closure: Wrap tie closure 
Fabric: 100% Cashmere
Care: Dry clean

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 $385 Buy Now AT AMAZON

Autumn Cashmere Wrap Dress $385 Buy Now AT SHOPBOP

ASOS Design Edition Feather Dress 

Best Festive Cocktail Party Dress

Sizes 0-16
Fabric: Polyester with faux feathers and rhinestones
Care: Hand wash, dry flat

Whether you're headed to a New Year's Eve party, a black tie, or a cocktail 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 $234 Buy Now AT NORDSTROM

Free People Oasis Maxi Dress

Best Boho Winter Dress

Colorways: Black floral or Lavender floral
Sizes: XS-XL
Fabric: 55% cotton, 45% rayon
Care: Machine wash, lay flat to dry

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 $168 Buy Now at nordstrom

Proenza Schouler Drop Waist Faux Leather Dress

Best Leather Winter Dress

Sizes: 0-12
Fabric: Polyester
Care: Hand Wash

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 $695 Buy Now AT SHOPBOP

Anrabess Turtleneck Sweater Dress

Most Budget-Friendly Amazon Winter Dress

Colorways: Available in over 15 colors
Sizes: XS-XL
Fabric: 50% viscose 30% nylon and 20% PBT
Care: Hand wash only

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 $43.99 Buy Now AT AMAZON

Reformation Remi Floral Long Sleeve Minidress

Best Long-Sleeve Mini Winter Dress

Sizes: 0-12
Fabric: Viscose
Care: Dry clean

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 $218 Buy Now at nordstrom

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

Staud Etta Dress

Best Winter Feather Dress

Sizes: XS-XL
Fabric: 59% viscose/40% nylon/1% spandex
Care: Dry clean

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 $395 Buy Now at shopbop

Staud Etta Dress $395 Buy Now at mytheresa

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

Banana Republic Colletta Off-Shoulder Midi Dress 

Colorways: Everest and brown
Sizes: XXS-XL; regular and petite sizes
Fabric: 58% wool, 30% recycled polyester, 10% yak, 2% spandex.
Care: Dry clean only

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~~  $189.97 Buy Now AT BANANA REPUBLIC

Paco Rabanne Striped Luxe Long Dress

Sizes: XS-L
Fabric: 31% Cotton, 34% Nylon, 35% Metalized Polyester
Care: Dry clean

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 $1190 Buy Now AT LUISAVIAROMA

Everlane Cozy Stretch Turtleneck Dress

Best Winter Turtleneck Sweater Dress

Colorways: Charcoal gray, heather gray, lapis blue, taupe, and brandy 
Sizes: XXS-XXL
Fabric: 58% Wool, 30% Recycled Nylon, 10% Yak hair, 2% elastane
Care: Handwash cold, lay flat to dry or dry clean

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 $148 Buy Now AT EVERLANE

Simon Miller Space Dress

Best Casual Cutout Winter Dress

Sizes: XXS-L
Fabric: 92% rayon, 8% spandex
Care: Hand wash only

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 $206.50 Buy Now at amazon

Simon Miller Space Dress $206.50 Buy Now AT SHOPBOP

Simon Miller Space Dress $295 Buy Now AT NORDSTROM

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

Loulou Studio Striped Midi Dress

Best Cable Knit Winter Dress

Sizes: XS-L
Fabric: 90% merino wool, 10% cashmere

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 $560 Buy Now AT NET-A-PORTER

ASTR The Label Sweater Dress

Colorways: black and brown
Sizes: XS-XL
Fabric: 90% viscose, 10% elastane
Care: Dry clean

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 $89 Buy Now at nordstrom