How To Wear Dresses In Winter While Staying Warm And Stylish

It’s easy for pant and sweater combinations to dominate your winter wardrobe. They are quick and practical choices to get you through the cold weather. If you’re ready to break out of your seasonal style rut, may we recommend a dress? Keep reading for our top tips on how to wear dresses in winter, including your favorite frocks from summer.

How To Wear Summer Dresses In Winter

Figuring out how to wear dresses in winter is one thing, but what about summer dresses? Your warm-weather wardrobe knows the routine by now. The moment you wake up to the first chilly winter morning, its days are numbered. You quickly tuck all your dresses fit for the sun into the back of your closet. But just because you’re saying so long to summer doesn’t mean you have to say goodbye to the dresses. With the help of cozy layering pieces and the right accessories, you’ll ace how to wear summer dresses in winter. First up, the spaghetti strap dress.

How to Wear Spaghetti Strap Dresses In Winter

Wondering how to wear a spaghetti strap dress in winter? We say throw it back to the 90s. Going sleeveless when the mercury’s falling might seem unthinkable, but trust us. Layering a long sleeve, fitted knit top under your dress will earn you style points and warmth all in one. If your dress is a lightweight material like silk and rayon, we recommend opting for a thinner top. This will avoid adding bulk to your outfit or disturbing the design of your dress. Step into a pair of statement-making animal-print boots and keep the nostalgia train going with a retro baguette bag.

How to Wear Short Dresses in Winter

The simplest answer to the question of how to wear short dresses in winter is with a pair of tights. Use a neutral colored pair to let a patterned dress shine. Alternatively, make hosiery the star of the show with saturated shades of plum or mustard. When picking your perfect pair, play around with different thicknesses. This way, you’ll be just as comfortable and stylish in a winter storm as you are in moderate temps. With so many ways to wear tights, you’ll leave the days of cold legs behind.

Got a run in your stockings? No worries. Melt away any winter blues with over-the knee boots instead. Grab a fitted mini dress from your closet and channel your inner 70s-style disco diva with this combination. Throw on a cable-knit sweater for a touch of texture, grab a peppermint latte and enjoy a snowy stroll. 

How to Wear Maxi Dresses In Winter

Interested in earning your style adventurer badge? Then it’s time to learn how to wear maxi dresses in winter. Instead of wearing tights, up the ante with leggings or even skinny pants under your dress. This is an ideal way to carry both maxi and midi frocks into the winter season. Create an edgy, chic-style silhouette with faux leather skinnies underneath a straight-cut maxi dress.

Embrace this long line look with a duster cardigan, or draw attention to your hemline with a waist-length jacket. This trick isn’t strictly reserved for summer dresses either. Your sweater dresses (aka the original winter dress) can get in on the fun as well. All that’s missing now is the right pair of shoes.

What Shoes To Wear With A Maxi Dress In Winter

In the summer, you can count on trusty wedges and sandals to go with any maxi dress in your closet. In winter, however, you’ll want to avoid Jack Frost actually nipping at your toes. When deciding what shoes to wear with a maxi dress in winter, you can’t go wrong with ankle boots. Lug-sole boots are a seasonal staple of 2022 women’s winter fashion trends. They’ll just barely peek out from under the long hemline of your dress while also helping you balance on icy sidewalks.

Got a maxi dress you want to wear to the office? After slipping on a blazer, complete your look with the ultimate workleisure shoe: the loafer. This always-sleek shoe will give your outfit the professional lift it needs. Don’t worry, we’ll have more on shoes later. For now, congratulations! You’ve completed the summer dress edition of how to wear dresses in winter. Now, it’s time to embrace the time of year in holly-jolly velvet frocks.

How to Wear A Velvet Dress In Winter

Not sure how to wear a velvet dress in winter? By turning it into your go-to party outfit, of course. Look no further for what to wear to your next holiday party than a velvet dress. This shimmery style fits right in at any yuletide gathering or New Year’s Eve bash. Make all things merry and bright with a dress in lush emerald green or stormy sapphire. Lean into this sophisticated look by wearing pearls or classic gold hoop earrings. Let the signature texture of velvet take the spotlight by skipping sherpa or woolly layers. Instead, try a simple overcoat or long-sleeved dress to keep you warm as you ring in another year. Cheers!

How To Wear Denim Shirt Dresses In Winter

You’ve likely seen denim dresses dominating spring and fall fashion. They’re a favorite of transitional months thanks to denim’s breathable and easy-to-layer cotton fabrication. Here are a few tips on how to wear denim shirt dresses in winter. Wear a waffle knit henley under the dress or layer on a crew-neck sweater with on-trend balloon sleeves. If your denim dress has a collar, don’t be afraid to pull it outside your sweater for a preppy aesthetic. Keep this clean-cut look going with knee-high socks and a knotted headband.

Want to give this frock a little more edge? Select a moody denim shirt dress in a black or dark grey wash. Amp up the volume with black tights, combat boots and an oversized leather jacket. Whichever style you choose, the shirt dress might just replace jeans as your favorite denim outfit this season.  

Finishing Touches For Winter Dresses

You’ve got your dresses lined up and are ready to battle the elements. But before we dub you a true master of how to style dresses in winter, let’s talk finishing touches. You know, those little details or supporting players that take your look to new heights. First on our list: block out the blustering air with outerwear.


Outerwear has your back no matter what outfit you rock this winter, but this is especially true with dresses. Since you might have more skin exposed, taking layering seriously is key to how to wear dresses in winter. From shackets to overcoats, there’s no end of snuggly options to instantly revamp your dress into a winter wonderlook. For warmer climates, opt for a utility jacket or trucker-style jean jacket to add just the right amount of heat. In icier locales, bundle up in a cabincore style fuzzy robe coat or teddy bear quarter-zip.

Another outerwear tip for how to style dresses in winter? Make sure the length of your coat or jacket complements the length of your dress. A waist-length vinyl jacket shows off the shape of a knee-length A-line dress. For midis or maxis, try a shacket that hits at the hip to define your figure. Now that you’re living it up in layers, let’s check out the finishing touches to boost your dresses for winter.


When it comes to how to wear dresses in winter, boots are the real MVP. They’re the epitome of style and function, so you can count on them to get your winter dresses to the gold. Booties are great for milder temperatures or when paired up with thick knit socks and tights. When temperatures start to feel arctic, reach for tall boots. This timeless style will take you anywhere this winter, from a festive dinner party to knocking out last-minute shopping.

When you want more variety on how to style dresses in winter, go for closed-toe heels and flats. Pumps with jewel embellishments elevate any end-of-year look and shearling-lined slip-ons will keep your shivers at bay. 


If you’re looking for guidance on how to style dresses in winter, remember, it’s all in the details. 

While brightly colored accessories are popular summer choices, dark neutrals and warm tones complement the latter half of the year. Leave your cotton totes and linen beach bags for next summer. Take on après-ski fashion with faux-fur satchels and sturdy vegan leather crossbodies. Small touches like tall socks or a smartly knotted scarf are enough to make dresses your cold-weather ride or die. 

Ready to give your dress collection a new lease on life? Our expert stylists are here to assist with all of your winter fashion needs. Take your style quiz, order a Fix and don’t forget to ask your stylist for fresh winter dresses and accessories. Sit back, relax and receive five curated pieces right at your doorstep that you can try on at home. Keep what you love and send back the rest. Shipping and returns are always free.

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