You don’t need to sacrifice style for warmth—wearing a dress in the winter can be an effortlessly chic solution to cold weather if you do it right.
The key is reworking your favorite dress outfits to fit both the chilly temps and your own unique style and wardrobe. Do you love wool knits and maxi-length pieces? Or are you keen to level up your layering skills with tights and high socks?
Browse the nine best dresses for winter and wear what you love in any season.
These nine winter dress outfits will help you find new cold-weather staples and keep old favorites out of storage. Here’s how to wear a dress during winter (or whenever you feel a chill).
The maxi sweater dress is a smart cold-weather choice—cozy, subtle, and flattering on every body type. Our go-to choices are wool and cashmere for the best blend of warmth and style.
This type of dress is incredibly adaptable. Add elegant earrings and a thin belt for a party look, or wear a knit cap and boots for a snowy day downtown. For warmer days, throw on a comfy pair of sneakers.
H&M’s Knit Long Dress is our favorite. It’s comfortable, versatile, and alluring. Thrift one of H&M’s top-notch sweater dresses on ThredUp, starting at $7.99.
A trench coat dress allows you to wear both a winter coat and a dress in one. Go for a traditional vintage look with long sleeves and maxi length, adding a warm scarf and beret for an effortless preppy aesthetic.
Prefer a modern look? Try a sleeveless trench layered with a turtleneck, thermal leggings, and knee-high boots.
We adore Ralph Lauren’s Charley Crepe Trench Dress, which smoothly incorporates epaulets and storm flaps into a sleek, feminine dress. This preppy brand offers many unique trench dresses. Find them on ThredUp, starting at $18.99.
You don’t need ankle-length dresses to keep out the cold. Midi turtlenecks are fashionably contemporary and offer numerous styling opportunities.
Our favorite combo is a cream turtleneck dress with tights, a plaid scarf, and a wool coat. Runner up: a gray midi with stockings, a black puffer trench, and a knit hat.
Remember that not all turtleneck dresses are knit. In warmer climates, lighter materials like velvet and cotton provide protection without the bulk. We’ve seen great dresses from Free People, like their Anna Sui Posie Stretch, a velvet turtleneck dress with an eye-catching floral pattern.
Browse hundreds of Free People turtleneck dresses for budget-friendly prices on ThredUp, starting at $19.99.
A long sleeve is the perfect day-to-night outfit—wear it to the office and effortlessly transition to a holiday party in the evening. You can choose any length, from mini to maxi.
We also recommend this style for a winter wedding with a cocktail attire dress code. Try a navy mini, and accessorize with a pair of toasty stockings and a neutral cardigan.
Everlane’s Riviera is our number one midi pick, and their Form is our top mini. This sustainable brand produces the most sleek, sophisticated dresses, and you can find them on ThredUp, starting at $27.99.
You can stave off the cold and be completely captivating at the same time. A knit bodycon dress showcases your curves and confidence. It’s appropriately warm, but it’s also the perfect party dress.
Pair a knit bodycon midi with a leather jacket, infinity scarf, and slouchy knee-high boots for a dressy dinner date. For an easy variation, wear a maxi dress with leggings and swap in a pair of ankle boots.
Luxury designer Enza Costa offers gorgeous bodycon dresses—we recommend the Silk Sweater Knit Mockneck Dress, a soft, simplistic maxi. Check out our collection of Enza Costa dresses that won’t empty your wallet, starting at $21.99.
Nothing’s cozier than a cardigan in the winter, so why not make it the central piece for your look? While cardigan dresses are similar to sweater dresses, the front closure makes them easier to layer (and also prevents messy hair syndrome).
Keep it simple for a holiday party, and pair a chocolate brown cardigan dress with tan ankle boots. For extra cold occasions, like winter hikes and sleigh rides, layer a cardigan dress with a winter jacket, leggings, and snow boots.
Our top choice is the Staud by Saks Fifth Avenue. This rib-knit cardigan maxi sports an elegant V-neck and a line of buttons down to the knees. Check out our collection of preloved cardigan dresses from Saks, starting at $19.99.
Reap the benefits of warm, durable denim without swapping your dresses for jeans. A long-sleeve denim shirtdress is surprisingly toasty on its own, but adding a pair of leggings is perfect for a particularly frosty day.
Style this with knee-high or cowboy boots, and for extra country vibes, dare for double denim and a fur-lined jean coat.
Madewell has our favorite jeans, and the same goes for their denim dresses. We love their Western Midi Shirtdress, a medium denim wash midi with a flexible front slit and five-pocket skirt. Discover hundreds of Madewell dresses on ThredUp, starting at $8.99.
Trying to ace those cottagecore vibes? Look dreamy and whimsical this winter by donning a puff-sleeve maxi.
Layer a thin cotton long-sleeve shirt under a puff-sleeve dress to enhance the warmth and comfiness of this style. Add a scarf or swap in a turtleneck if you’re going out into a cold wind.
If you wear this to a holiday party, opt for simplicity— just the dress without the layers. Stay warm on the way there with a relaxed wool coat that won’t crunch or wrinkle your sleeves.
For both ideas, we recommend Zara’s Embroidered Dress with Balloon Sleeves. Its lace trim and billowing frame provide a striking fairytale aesthetic.
Love Zara’s dresses but not their fast-fashion framework? Reduce your fashion footprint by thrifting them on ThredUp, starting at $7.99.
Pinafores are great winter dresses, suitable for quaint, country aesthetics and sophisticated academia.
Create a smooth faux jumpsuit with a matching long-sleeve shirt and leggings under your pinafore. Add a beret and a pair of slingbacks for a cute party look.
For something more subtle, wear a neutral wool pinafore with a white turtleneck and Oxford shoes.
Banana Republic offers understated, feminine pinafores—we like the Eyelet Pinafore Sheath, with its lace detailing and ruffled accents.
Try grabbing one of this brand’s top-tier pinafores on ThredUp, starting at $6.99.
Cold weather isn’t the time to put away your favorites—it’s the time to get creative, learn to layer, and thrift new must-have winter dresses.
ThredUp is the best platform to buy dresses online—quick, convenient, and sustainable. Navigate our vast collection of dresses and matching accessories with our Improved Search function. You can simply enter search terms like “warm sweater dress with holiday vibes,” and we’ll send you curated results.
If you need a little inspiration, bounce ideas off our Style Chat. Describe an outfit, event, or aesthetic, and our AI chat will generate different looks. Once you love the results, shop suggested items from our collection.
It depends! With the right layers, like leggings, coats, and scarves, you can easily adapt breezy cotton dresses to cold weather. But wearing strapless summer dresses or pieces with spaghetti straps and mesh panels might be tricky.
Plenty of shoes go well with maxi dresses in chilly weather. Our favorites are ankle boots, sneakers, and loafers. We also love knee-highs, but they work best if your maxi dress has a slit.
Different coats work well with different maxis. Pair a trench coat with a stunning evening gown for some elegant flair, or add a bomber jacket to a bodycon dress for a waist-defining touch. Consider the shape and bulk of your dress—you don’t want to crush any embellishments with a tight coat. Finding a relaxed jacket for this style is best.
