A person showcases how to style a dress for cold weather by wearing the FOR LOVE & LEMONS Casey black lace maxi dress, featuring short sleeves and a slit. Their long hair is tied back as they look down against a beige backdrop, with black boots giving an edgy touch to the outfit.

FOR LOVE & LEMONS

The Dress Edit

Winter Is Coming, Here’s How To Wear A Dress In Cold Weather

With temperatures dropping swiftly, we all need to know how to wear a dress in cold weather. After all, our love frocks won’t stop just because of a chill in the air! So, from weekend brunch dates and low-key dinners to special occasions, I’ve found all the best dresses, shoes, and bags to wear together to beat the cold in style. Keep scrolling to shop the season’s best and most beautiful silhouettes from Free People, Isabel Marant, Diane Von Furstenburg, and so many more. 

Dressed elegantly in a DOEN Oliana long sleeve floral maxi dress, a person stands gracefully amid tall grasses, demonstrating how to style this dress in cold weather. The backdrop of trees and the warm, natural sunlight enhance the scene.

DÔEN Oliana Dress

A person showcases how to style the FREE PEOPLE In The Garden white mini dress for cold weather, pairing it with a cozy headband and sturdy brown boots. They stand in a field of lavender, set against green hills and trees under an overcast sky.

FREE PEOPLE In The Garden Mini Dress

How To Wear A Dress In Cold Weather With Knee-High Boots

Whenever someone asks me how to wear a dress in cold weather without compromising on style, I always utter three words. Knee-high-boots. Whether you’re braving the chill with a mini dress or leaning into the boho-chic trend with a floral maxi design, knee-high boots will compliment a dress in cold weather every single time. For example, take the Oliana dress by Doen. Firstly, it draws you in with a moody floral print that couldn’t be more ideal for this time of year. Secondly, those darker color tones lend themselves beautifully to suede knee boots like the Jane Botta 55 suede knee boots by Christian Louboutin. Finally, add the Oskan soft bag by Isabel Marant for a flawless boho ensemble. 

Meanwhile, if you’re all about shorter hemlines, even in chilly weather, knee-high boots will be your best friend. My favorite pairing right now? The charming, In The Garden mini dress by Free People, and the Voyou leather buckle knee boots by Givenchy. The quintessential mix of pretty and edgy, this dress and these boots are a match made in heaven. Finish off the look with the Callista slim-grained leather tote – before it sells out!

Shop more Cold Weather Dresses selected and reviewed by our expert fashion buyers and stylists

  • ISABEL MARANT Elidia Dress in Plain-Colored Crepe with English Embroidery

    $825
  • ISABEL MARANT Carly Gathered Midi Dress in Lambskin Leather

    $3,790
  • DIANE VON FURSTENBERG Gizelle Jacquard Dress

    $538
  • DIANE VON FURSTENBERG Astrid Wool-Cashmere Wrap Dress

    $558
  • CURRENT AIR Laraline Paisley Jacquard Midi Dress

    $155
  • CURRENT AIR Ruffled Mini Sweater Dress

    $138
  • SHOW ME YOUR MUMU Bonfire Sweater

    $148
  • MAEVE Long-Sleeve Collared Sheer Mini Dress

    $168
  • ENGLISH FACTORY Faux-Leather Mini Shift Dress

    $90
  • AFRM Kay Long-Sleeve V-Neck Mesh Maxi Dress

    $128
  • MAEVE Short-Sleeve Collared Slim Midi Dress

    $168
  • ISABEL MARANT Albini Gathered Printed Silk-Blend Midi Dress

    $1,390
  • FREE PEOPLE In The Garden Mini Dress

    $248
  • FREE PEOPLE Sunkissed Mini Dress

    $168
  • FREE PEOPLE Freya Floral Mini Dress

    $198
  • FREE PEOPLE Hampton Mini Dress

    $168
  • FAITHFULL Paloma Open-Back Silk-Voile Maxi Dress

    $500
  • ULLA JOHNSON Celia Pleated Paisley-Print Wool-Blend Twill Midi Dress

    $750
  • LOVERS AND FRIENDS Caddie Mini Dress

    $138
  • ANTHROPOLOGIE Tommie Cap-Sleeve Shirt Dress

    $168
  • ANTHROPOLOGIE Sheer Lace Tunic

    $130
  • ANTHROPOLOGIE Cap-Sleeve Midi Dress

    $188
  • HOUSE OF HARLOW 1960 Marni Dress

    $158
  • L’ACADEMIE Marianna Izel Mini Dress

    $208
  • LPA Fallon Sweater Dress

    $148
  • ALLSAINTS Xylia Maxi Dress

    $229
  • DÔEN Oliana Dress

    $498
  • ULLA JOHNSON Gemma Broderie Anglaise Cotton-poplin Mini Shirt Dress

    $490
  • MAX MARA Leisure Faro Topstitched Denim Midi Dress

    $295
  • FOR LOVE & LEMONS Casey Black Maxi Dress

    $279

How To Wear A Dress In Cold Weather When You Only Wear Mini Dresses

Want to know how to wear a dress in cold weather when all you own is minis? Unless it drops below zero, layering means mini dresses are fair game in the winter months! Add tights, boots, knitwear, and an overcoat, and you’re all set to show off your fave short dresses – even in January. With that said, thin cotton dresses, of course, won’t stand up to the chill. Instead, I’ll be stocking my closet with wool designs, like the ruffled mini sweater dress by Current Air. Slip into this essential black mini dress with the Atomic woven leather cylinder-heel booties by Bottega Veneta, and the Milano padded debossed bag by Gucci.

Lastly, winter doesn’t mean your closet has to be devoid of color. And, the Sunkissed mini dress by Free People is proof. Pair this deep red silhouette with black boots, preferably the Carolyn patent stiletto sock booties by Jimmy Choo. Then compliment both with the Sierra studded leather-trimmed shoulder bag by Isabel Marant. 

Shop All Cold Weather Dresses

A person with a ponytail sits on a modern metal chair, perfectly illustrating how to wear a dress in cold weather. They sport the CURRENT AIR Ruffled black mini dress and cozy black ankle boots. The plain, light-colored background highlights their chic ensemble.

CURRENT AIR Ruffled Mini Sweater Dress

A person demonstrates how to wear a dress in cold weather by pairing the FREE PEOPLE Sunkissed red velvet mini dress with tall brown lace-up boots. Holding a brown handbag, they stand against a plain white background, one foot slightly raised.

FREE PEOPLE Sunkissed Mini Dress

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