A woman showcases a winter look on a city sidewalk by wearing the FREE PEOPLE Vera mini black leather dress paired with sheer stockings and a gray jacket. With a black handbag in hand, she stands against the backdrop of a brick building and bustling street, embodying chic daytime style.

FREE PEOPLE

The Dress Edit

Tips From A Stylist: How To Wear A Mini Dress In Winter

Midis and maxi dresses are great but if you love short silhouettes like me, you want to know how to wear a mini dress in winter. The good news is, that there are countless ways to style your favorite short dresses for both work and weekend days. Plus, they still make the ideal cold weather evening looks with a few simple styling tips. Keep on reading for my top tips, alongside the best new-in designer mini dresses, bags, and shoes to make your mini-dress outfits the most stylish they can be.

A person demonstrates how to wear a mini dress in winter by pairing the FREE PEOPLE Freya brown velvet mini dress, adorned with intricate embroidery, with knee-high boots. They hold a matching brown jacket while standing against a plain white background, highlighting the ensemble's cozy elegance.

FREE PEOPLE Freya Floral Mini Dress

Standing against a dark gray background, the person elegantly demonstrates winter styling by layering a white blouse under the BLACK HALO Roanna black sheath dress. They pair it with knee-high boots, striking a confident pose with one hand on their hip and the other relaxed as they look to the side.

BLACK HALO Roanna Sheath Dress

How To Wear A Mini Dress In Winter With Boots

One of the simplest and most stylish answers for how to wear a mini dress in winter? Add a pair of cold-weather boots. From ankle boots to knee-high styles, they’ll make your mini-dress outfits instantly chicer and warmer. For example, the Freya floral mini dress by Free People. With a warming velvet fabric and the ultimate fall/winter color palette, this pretty, brown puff sleeve dress with floral detailing is the ultimate off-duty dress. Stay on color theme and pair yours with the Vicky 90 ankle boots by Saint Laurent and the Vela small woven bag by Etro. Finally, tights and a long wool coat will perfectly contrast this ensemble while fighting off the chill.

Meanwhile, opt for the Roanna sheath dress by Black Halo when the occasion calls for something a little smarter. Layer your look for warmth and wear this dress over a long-sleeved shirt or sweater. Then, add sleek black leather knee boots, a matching black bag, and a weather-appropriate trench coat. I highly recommend the Voyou leather buckle knee boots by Givenchy and the double G crossbody leather bag by Gucci.

Shop more winter mini dresses selected and reviewed by our expert fashion buyers and stylists

  • DIANE VON FURSTENBERG Sonoya Dress

    $418
  • SAINT LAURENT Open Back Velvet Skater Mini Dress

    $4,250
  • ISABEL MARANT Felie Short Dress with English Embroidery

    $770
  • ISABEL MARANT Dulce Viscose Short Dress

    $690
  • VALENTINO GARAVANI Long-Sleeve Ruffled Mini Dress

    $4,500
  • LOVESHACKFANCY Lavender Pointelle-Knit Mini Dress

    $495
  • ISABEL MARANT Daphne Dress

    $1,590
  • DIANE VON FURSTENBERG Sheska Dress

    $398
  • CURRENT AIR Chevron Pleat Mini Dress

    $138
  • CURRENT AIR Ruffled Mini Sweater Dress

    $138
  • SHOW ME YOUR MUMU Bonfire Sweater

    $148
  • BLACK HALO Roanna Sheath Dress

    $415
  • MAEVE Long-Sleeve Collared Sheer Mini Dress

    $168
  • MAEVE Puff-Sleeve Keyhole Embroidered Mini Dress

    $178
  • FREE PEOPLE Sunkissed Mini Dress

    $168
  • FREE PEOPLE Freya Floral Mini Dress

    $198
  • VALENTINO GARAVANI Cotton-Blend Velvet Mini Dress

    $4,900
  • HOUSE OF HARLOW 1960 Marni Dress

    $158
  • L’ACADEMIE Marianna Izel Mini Dress

    $208
  • VERONICA BEARD Saude Shirtdress

    $498
  • ELLIATT Revolve Asta Mini Dress

    $260

How To Wear A Long-Sleeve Mini Dress In Winter

If you’re wondering how to wear a mini dress in winter and stay warm, look out for long sleeves. These dresses will make your outfit much more wearable as temperatures drop, plus, they look seriously chic! For example, the chevron pleat mini dress by Current Air. Firstly, this sleek navy dress is ideal for day-to-night events this party season. Secondly, it looks stunning with both heels and boots. My advice? Slip into this dress with tights, your go-to winter coat, and a classic pair of black leather boots. Invest in a pair like the pointed-toe booties by Gucci that will serve you and your closet for countless seasons to come. Then, add the Givenchy Voyou small shoulder bag to finish your look.

Lastly, we all need the perfect little black dress in our closets. The Lavender pointelle-knit mini dress by Loveshackfancy is destined to sell out and will see you stylishly through countless smart and casual events this winter. Pair it with the Santia knee-high boots by Christian Louboutin and the Bayswater, grained leather satchel bag by Mulberry for a timeless outfit you’ll reach for on repeat.

Shop All Winter Mini Dresses

A woman stylishly showcases the CURRENT AIR Chevron pleat navy mini dress, featuring long sleeves and a textured pattern along the waist and hem, perfect for winter wear. She stands against a plain background, glancing to the side.

CURRENT AIR Chevron Pleat Mini Dress

A woman with long, wavy hair demonstrates how to style the LOVESHACKFANCY Lavender black long sleeve knit dress for winter. The dress features a scoop neckline, and she stands against a neutral background, casually holding the hem with one hand.

LOVESHACKFANCY Lavender Pointelle-Knit Mini Dress

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