I Refuse to Ditch My Dresses—23 Winter-Ready Outfits I'm Re-Creating Instead

how to wear dresses in the winter shown in a collage of women wearing dresses

Do you feel the cold front coming on? Like it or not, winter is coming. While some may relish the idea of colder temperatures, I can't relate. Just because winter is coming doesn't mean I'm ready to part ways with my dresses. As much as I know I "should" want to slip into a pair of trendy jeans, I just don't have the desire to deal with them. Putting on pants is daunting, so I try to circumvent them as much as possible. You could say I'm in denial, especially considering the cold temperatures, but I know I'm not the only one who feels this way. If you clicked on this article, you, too, aren't looking forward to the potential prospect of packing away your favorite frocks. Frankly, I don't blame you.

There's an ease that comes with just throwing on a dress and heading out the door, which is why I've spent so many years trying to find out how to wear dresses in the winter. I've learned that it's possible not to sacrifice warmth if you choose the right type of dress (e.g., leather or sweaterdress options) and are intentional with your styling. Knowing how to layer correctly is half the battle of making any dress winter-ready—it's an art form. While it takes a great deal of expertise to make dresses work in the winter, you can learn it. In the vein of helping you, I'm sharing some of that knowledge by showcasing how real women from around the world make this item winter-ready.

Ahead, you'll find a curation of 24 winter dress outfit ideas, styling tips, and even shopping recommendations that will make you less weary about wearing dresses in the winter. Consider them your permission slip to skip out on pants this season.

a photo showing how to wear dresses in the winter with a woman wearing a long black wool coat over a gray knit maxi dress and black ballet flats

(Image credit: @_marisamartins_)

WEAR: Longline Wool Coat + Clutch Bag + Maxi Sweaterdress + Ballet Flats

The secret to pulling off dresses in the winter comes down to having one staple on hand: a sweaterdress. When in doubt, you can't go wrong with pairing a longline coat with a maxi sweaterdress and ballet flats—it's a failproof formula for easy and elegant winter dressing.

a photo showing how to wear dresses in the winter with a woman wearing a black crewneck sweater over a white maxi dress with black loafers and a red satin bag

(Image credit: @styleidealist)

WEAR: Crew-Neck Sweater + Chain Necklace + White Maxi Dress + Red Shoulder Bag + Red Socks + Loafers

While it's definitely better to opt for dresses made from thicker textiles in the winter, that doesn't mean you must. In fact, you can make the more summer-feeling white maxi dress work for winter by layering a crew-neck sweater over it and adding colorful socks or hosiery.

a photo showing how to wear dresses in the winter with a woman wearing a brown moto jacket over a black dress with pumps and a crescent shoulder bag

(Image credit: @annabelrosendahl)

WEAR: Sunglasses + Moto Jacket + Black Dress + Pumps + Crescent Shoulder Bag

Just because it's cold outside doesn't mean you can't look cool. (Excuse the pun.) When it comes to dressing for winter, don't be afraid to ditch your pants instead of wearing a black ribbed dress with a moto jacket, pumps, and a crescent shoulder bag. It's a look that will work for whatever winter plans are on your agenda.

a photo showing how to wear dresses in the winter with a woman wearing a black long leather coat over a white turtleneck dress with black knee-high boots

(Image credit: @rikkekrefting)

WEAR: Leather Coat + Turtleneck Dress + Chunky Chain Necklace + Handbag + Knee-High Boots

Do you consider yourself more of a minimalist? Rather than committing to a moto jacket, make a minor swap to a timeless leather trench. Styling this outerwear over a turtleneck sweaterdress with simple accessories will embody the '90s-minimalism aesthetic.

a photo showing how to wear dresses in the winter with a woman wearing a blue knit polo under a leather mini dress with a black shoulder bag, hoop earrings, and sunglasses

(Image credit: @lefevrediary)

WEAR: Sunglasses + Hoops + Knit Polo + Leather Dress + Shoulder Bag + Pumps

One of the hardest things about dressing during the winter is being able to choose what to wear for various occasions, including work. If you're like me and don't want to part with your dresses, then there's only one thing you can do: invest in a leather dress. Not only will opting for this textile ensure you stay warm, but it's also the perfect staple for the office. Make it feel formal by pairing it with a knitted polo, pumps, hosiery, and outerwear.

a photo showing how to wear dresses in the winter with a woman wearing a tan coat over a black bodycon knit dress with gold sculptural earrings and a black clutch bag

(Image credit: @iliridakrasniqi)

WEAR: Sculptural Earrings + Coat With Built-In Scarf + Body-Con Sweaterdress + Clutch + Tights + Pumps

It's not just dressing for work that's a challenge. If I'm being honest, no one wants to wear a million bulky layers on a date—hence the appeal of dresses. If you're worried this item won't work for your winter-date plans, take inspiration from the look above. Opt for a fitted knit dress with tights, pumps, sculptural earrings, a clutch bag, and a coat with a built-in scarf.

a photo showing how to wear dresses in the winter with a woman wearing a white turtleneck neck under a black mini dress with black knee-high boots

(Image credit: @_livmadeline)

WEAR: Turtleneck + Minidress + Riding Boots + Shoulder Bag

Another way to ensure your dresses are equipped for cold weather? Always opt for base layers, like the look above. Even if you're planning on wearing thermal tights or a thick winter coat, it's worth layering a light turtleneck underneath a minidress to ensure maximum warmth.

a photo showing how to wear dresses in the winter with a woman wearing a black turtleneck over a sheer sequin dress that's layered over white trousers with black mary jane pumps

(Image credit: @maryljean)

WEAR: Shoulder Bag + Turtleneck + Sheer Dress + Trousers + Mary Janes

Not only can minidresses be made winter-ready by layering, but so can sheer ones! Don't believe me? Look at the outfit above. By layering your sheer dress over trousers and underneath a chunky turtleneck, you can extend the item's life cycle and add visual intrigue to any otherwise simple winter outfit.

a photo showing how to wear dresses in the winter with a woman wearing a black nipped waist blazer over a white ballon dress with black ankle strap pumps

(Image credit: @hannamw)

WEAR: Sunglasses + Wool Blazer + Drop-Waist Dress + Pumps

Ample layers are required to make dresses more winter-proof for those in cold climates. If you are lucky enough to live somewhere warmer, you may not need to add thermal underpinnings or oversize overcoats into the mix. If that's the case, style a well-tailored wool blazer over a dramatic dress with pumps or boots to make your frock feel wintry.

a photo showing how to wear dresses in the winter with a woman wearing a black puffer coat over a sweater dress with sheer tights and black flat mary janes

(Image credit: @nlmarilyn)

WEAR: Headband + Sweaterdress + Long Puffer Coat + Woven Bag + Tights + Mary Janes

If a blazer won't cut it, you'll want to turn to a cozier option like a puffer coat. While this outerwear might not seem like the most flattering silhouette, it can be if styled right. Take a cue from the outfit above and pair the coat with a sweaterdress, a headband, a woven shoulder bag, thermal tights, and ballet flats.

a photo showing how to wear dresses in the winter with a woman wearing a tan wrap coat over a turtleneck white mini dress with black tights, white socks, black knee high boots, and a white shoulder bag

(Image credit: @juliesfi)

WEAR: Sunglasses + Turtleneck Dress + Wrap Coat + Crossbody Bag + Tights + Knee-High Socks + Tall Boots

Not a fan of puffer coats? I totally get it. You can still be warm without feeling like a toasted marshmallow by opting for a wrap coat. Style the outerwear over a thick turtleneck sweaterdress with tights, socks, and knee-high boots for a cozy yet chic winter ensemble.

a photo showing how to wear dresses in the winter with a woman wearing a long navy coat over a black mini dress with sheer black tights and black mary jane flats

(Image credit: @borislavasekova)

WEAR: Headband + Sunglasses + Black Minidress + Navy Coat + Tights + Mary Janes

In addition to the wrap and puffer jacket, a tailored double-breasted coat works well for making your dresses winter-ready. Just be sure to draw inspiration from the outfit above and add trendy elements into your look—like a headband, sunglasses, tights, and Mary-Jane shoes—to ensure the outfit works.

a photo showing how to wear dresses in the winter with a woman wearing a white turtleneck dress under a matching zip-up jumper styled with black knee high boots and a black shoulder bag

(Image credit: @astyleedit)

WEAR: Zip-Up Jumper + Turtleneck Dress + Shoulder Bag + Boots

Consider this your sign that a coat is not the only way to winterize your dresses. By styling a turtleneck dress underneath a chunky zip-up jumper with knee-high boots and a shoulder bag, you get the same functionality as other winter outfits with half the bulky layers.

a photo showing how to wear dresses in the winter with a woman wearing a white puff sleeve dress under a black sweater dress styled with black combat boots

(Image credit: @dinahansen)

WEAR: Hoop Earrings + Puff-Sleeve Dress + Sweater-Vest + Combat Boots + Furry Handbag

In addition to adding a jumper to the mix, you can opt for other knitwear—ahem, sweater-vests. Take this preppy staple and give it the cool factor by pairing it with a puff-sleeve dress, combat boots, and a furry handbag.

a photo showing how to wear dresses in the winter with a woman wearing a black turtleneck dress under a long white duster cardigan styled with a black belt, knee-high boots, and a shoulder bag

(Image credit: @oliviafaeh)

WEAR: Sunglasses + Turtleneck Dress + Long Cardigan + Belt + Knee-High Boots + Shoulder Bag

For those who love the idea of layered knitwear but know a sweater-vest won't be warm enough, you'll want to take a cue from the outfit above. When you style a duster cardigan over another knit dress with knee-high boots, you're sure to be warm. If you're worried about layered knits looking too bulky, add a belt for final measure.

a photo showing how to wear dresses in the winter with a woman wearing a gray sweaterdress over blue jeans with strappy sandals and a corset belt

WEAR: Oversize Sunglasses + Sweaterdress + Corset Belt + Jeans + Sandals

Stacking on the knits is a safe bet to ensure your dresses are fit for cold weather. But if you want to be a bit more daring this winter, then consider re-creating the look above. Styling a knit dress over denim with interesting accessories is a surefire way to spice up your staple sweaterdress.

a photo showing how to wear dresses in the winter with a woman wearing a white tunic sweater layered over black leather pants with black mules and a shoulder bag

(Image credit: @sylviemus_)

WEAR: Sunglasses + Tunic Sweater + Leather Pants + Mules + Shoulder Bag

On top of jeans being a great way to winterize dresses for the winter, so are leather trousers. These bottoms can make oversize sweaters that tetter into tunic territory less intimidating to wear. For an effortlessly elegant winter ensemble, pair a tunic sweater with leather trousers, a sleek shoulder bag, and either mules or boots depending on the weather.

a photo showing how to wear dresses in the winter with a woman wearing a black turtleneck dress layered under a tan shearling jacket styled with black sandals

(Image credit: @_jessicaskye)

WEAR: Sunglasses + Shearling Jacket + Turtleneck Dress + Sandals + Handbag

Possibly one of the easiest ways to make any dress warmer (besides pairing it with denim or leather) is to reach for a shearling jacket. Throw this fuzzy coat over a knitted dress, and it won't matter what the temperature is outside because you'll be toasty.

a photo showing how to wear dresses in the winter with a woman wearing a black and white fur coat layered over a black knit dress with white chunky lug sole boots

(Image credit: @sofiamcoelho)

WEAR: Shearling Coat + Shoulder Bag + Knit Dress + Chunky Lug-Sole Boots

Yes, I've already mentioned how fuzzy coats can make dresses feel 10 times warmer, but did I mention they can make them look cooler too? Even the simplest black knit dress can stun with the addition of a statement fur coat, a scarf, chunky lug-sole boots, and a shoulder bag.

a photo showing how to wear dresses in the winter with a woman wearing. a black turtleneck dress under a long gray coat with black over-the-knee boots and silver jewelry

(Image credit: @dawn.tan)

WEAR: Sculptural Earrings + Long Gray Coat + Black Turtleneck Dress + Leather Gloves + Over-the-Knee Boots

While donning a statement coat is undoubtedly an easy way to make any dress stand out in the drab winter months, it's not the only way. For the minimalists reading this story, one simply needs to play with contrasting neutrals to attract the same amount of attention. Draw inspiration from the look above by taking a gray coat and silver accessories and styling them with head-to-toe black for a look that's just as visually intriguing.

a photo showing how to wear dresses in the winter with a woman wearing a tan off-the-shoulder knit dress with black leather opera gloved, a chain necklace, bucket bag, and boots

(Image credit: @oumaymaboumeshouli)

WEAR: Chunky Chain Necklace + Off-the-Shoulder Knit Dress + Leather Opera Gloves + Bucket Bag

When you really want your new knitted dress to be the center of attention, you'll want to ensure your styling honors that desire. What better way to do just that than by adding leather opera gloves? Not only will this accessory keep your hands warm, but it will also draw attention to your dress. Note: Should you need a few extra layers, you can always add thermal undergarments and/or a minimal coat.

a photo showing how to wear dresses in the winter with a woman wearing a black long trench coat over a sequin maxi dress with furry flats

(Image credit: @sobalera)

WEAR: Sunglasses + Earrings + Long Trench Coat + Sequin Maxi Dress + Clutch + Furry Flats

Besides the notion that you "must" pack away your dresses, one of the worst things about winter is the sensation of having cold feet. Luckily, there's a solution to both quandaries: the outfit idea above. Styling a maxi dress with a longline trench coat and fuzzy shoes allows you to walk the fine line between opting for functional winter items and having fun with fashion.

a photo showing how to wear dresses in the winter with a woman wearing a long black coat over a brown ribbed dress with black ankle boots

(Image credit: @coco_floflo)

WEAR: Sunglasses + Earrings + Ribbed Dress + Long Coat + Shoulder Bag + Ankle Boots

By now, you hopefully have plenty of ideas on how to wear a dress in the winter. But if you're in need of one last nugget of wisdom, let it be this. It's all about styling. You do not have to follow "rules" about what you should be wearing in the winter, nor do you have to pack away your dresses. You just need to be willing to make a few simple swaps to make your dresses winter-forward. For example, a simple ribbed dress doesn't need to be styled with sandals. Rather, you can pair it with ankle boots and a longline coat. At the end of the day, any dress can be a winter dress if you dare to make it one.

This post was originally published at an earlier date and has since been updated.

Jasmine Fox-Suliaman
Editor

Jasmine Fox-Suliaman is a fashion editor living in New York City. What began as a hobby (blogging on Tumblr) transformed into a career dedicated to storytelling through various forms of digital media. She started her career at the print publication 303 Magazine, where she wrote stories, helped produce photo shoots, and planned Denver Fashion Week. After moving to Los Angeles, she worked as MyDomaine's social media editor until she was promoted to work across all of Clique's publications (MyDomaine, Byrdie, andBest Knockoff Luxury Clothing ) as the community manager. Over the past few years, Jasmine has worked onBest Knockoff Luxury Clothing 's editorial team, using her extensive background to champion rising BIPOC designers, weigh in on viral trends, and profile stars such as Janet Mock and Victoria Monét. She is especially interested in exploring how art, fashion, and pop culture intersect online and IRL.