How to Wear Dresses in the Winter, According to 5 Fashion Experts

Here are some tricks to try when you want to look cute but don't want to freeze.

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5 Stylists Reveal How to Wear Dresses In The Winter
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For many of us, (much) chillier temps are already popping up on our weather apps, almost mockingly prodding us to start piecing together our winter wardrobe. The good news is, if you aren't ready to completely overhaul your closet, you don't have to. The cold weather is a good time to make use of your favorite cozy staples, such as cozy sweaters, cardigans, and even dresses.

Yes, that's right: you can wear dresses in the winter, so don't be so quick to pack them away.

We're not just referring to sweater dresses, either. Minis, midis, maxis, your signature LBD — they're all fair game. It's really just a matter of how you style them amidst frigid forecasts.

During an exclusive interview with InStyle, celebrity stylist Cindy Conroy assured us that dresses can make for a great winter outfit. "I wear them almost 365 days a year," she adds.

As for how to wear dresses in the winter without looking out of season — or, worse, freezing — Conroy says "it all comes down to the right accessories." Think outerwear, footwear, and jewelry.

To better prepare you for dressing for the season (literally!), we reached out to five stylists for their best tips.

Layer Up

5 Stylists Reveal How to Wear Dresses In The Winter
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Ramy Brook Sharp, CEO and creative director of Ramy Brook, says the key to wearing a dress in the winter is — wait for it — layering.

"You can still wear your sleeveless dresses from summer, just layer by wearing something underneath it," she tells InStyle. "Opt for a button-down blouse or a turtleneck. A great leather jacket is going to go far during the winter because you can keep it on as part of your outfit or, pending the temperature outside or the place you are going, can take off and coat check."

View the Dress As A Blank Canvas

5 Stylists Reveal How to Wear Dresses In The Winter
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Then, build off it using outerwear and accessories that will totally transform the look, advises celebrity stylist, Mickey Freeman. His motto? Maximum impact with minimal effort.

"For example, for an evening look I would use a voluminous faux fox fur or feather shawl over a long-sleeve mini dress, which would act somewhat as a blank canvas. Pair with an embellished or metallic box clutch and complete with high-heeled booties to easily bring instant glamour to such a simple frock."

Be Strategic About Your Footwear

5 Stylists Reveal How to Wear Dresses In The Winter
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If you're wearing a dress made with thin material, Conroy suggests styling it up with ankle boots that are between 4-6 inches high (as long as you feel comfortable walking in them, of course).

"Those additional inches of material will protect your ankle and legs from the blistering cold and piles of snow mysteriously sneaking into your boot."

Choose a Puffer Vest Over Traditional Outerwear

5 Stylists Reveal How to Wear Dresses In The Winter
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Puffer vests are growing increasingly popular on social media (like this quilted number from H&M). They come in a variety of lengths and styles and, according to Freeman, make for an out-of-the-box combination when paired with a dress.

"They stylishly juxtapose each other," he tells InStyle. "The puffer vest's utilitarian vibe still being present, while the lack of sleeves help to maintain the visibility of the dress's overall form."

Choose Long Coats Over Cropped Styles

5 Stylists Reveal How to Wear Dresses In The Winter
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Staying warm is no small feat once temperatures start dipping below freezing, so while puffers and short tailored coats are oh so cute, Conroy would like to remind you that long outerwear is the name of the game when it comes to donning a dress.

"With so much airflow organically built into the garment, a long coat made of wool, shearling, faux fur or cashmere is your new best friend for staying toasty," she says. "The additional fabric acts as a blockade preventing the winter chill from seeping in. Even if you're wearing a mini dress, the coat incircles your legs so the cold is met with a bright red stoplight."

Go Punk

5 Stylists Reveal How to Wear Dresses In The Winter
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Thanks in large part to Kourtney Kardashian and Megan Fox, who have both given goth fashion a resurgence, all things punk-rocker are 'in' for the foreseeable future. We've been tempted to give the aesthetic a go, too, which Freeman says is a great idea when it comes to figuring out how to wear dresses in the winter.

"I would wear a form-fitting minidress under an oversized leather biker jacket, a distressed and oversized chunky-knit scarf, high combat boots, and Wolford fishnets to add a splash of punk rebelliousness," she says.

Add Shoulder Pads for an '80s Flare

5 Stylists Reveal How to Wear Dresses In The Winter
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While '90s grunge never really goes out of fashion, JLUX co-founders Teresa and Christina Jaide tell InStyle they're taking inspo from the '80s when it comes to styling dresses this winter.

"With colder weather upon us, we love finding stylish ways to revamp our favorite dress and still stay warm during the changing season," Christina tells us. "One of our favorite style tips is using shoulder pads! This simple secret works best when used with a knit or sweater dress as it may lack structure."

For added warmth, Teresa advises adding coverage where you need it most: your legs.

"Complete this look with over-the-knee boots, layer up with a coat that is longer than the dress, and you are winter-ready with style that's never compromised!"

This is Ask the Experts, where our favorite fashion know-it-alls share their wisdom. Just because you can trust your style instincts doesn't mean you should have to.

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