Clad confidently in a MAEVE red long sleeve mock neck sweater dress, ideal for those looking for guidance on winter dress styling. The dress features a matching belt and is complemented by a brown clutch, all set against a plain, neutral backdrop that highlights their chic outfit.

MAEVE

The Dress Edit

How To Style Winter Dresses For A Cold Weather Getaway

Need to know how to style winter dresses for an upcoming trip? I’ve got you covered. Whether you’re heading to a countryside retreat or treating yourself to a city break, these styling tips will help you beat the cold in style on your next vacation. Plus, if you’re in need of footwear and bags to elevate your new silhouettes, you won’t be disappointed. I made sure to include the season’s most sought-after boots and bags alongside my chicest cold-weather styling tips. Keep scrolling to discover fall and winter’s hottest silhouettes and accessories from Loveshackfancy, Veronica Beard, Diane Von Furstenburg, and more…

In a desert landscape, a woman demonstrates how to style winter dresses by shielding her eyes from the sun. She wears the dark, flowing SIR. Aries brown silk and lace maxi gown paired with knee-high boots, standing amid desert vegetation under a clear blue sky.

SIR. Aries Cut Out Gown

Against a pink backdrop, a person stands wearing a luxurious LOVESHACKFANCY Rialto cream floral maxi dress with ruffles and large hoop earrings. Holding the elegant garment draped over their arms, they showcase how to style winter dresses effortlessly. A patterned rug adds charm to the scene.

LOVESHACKFANCY Rialto Silk Maxi Dress

How To Style Winter Dresses With Layers

If you’re wondering how to style winter dresses with your fave knitwear and outerwear, stop scrolling. I have all the tips you need. Firstly, let me recommend trying this style hack with maxi-length dresses. Long-sleeved options are, of course, a winter staple. However, they can feel a little bulky under more than one layer. With that in mind, try opting for sleeveless, silky dresses like the Aries cut-out gown by Sir. This stunning cut-out lace design will look incredible with designer knee boots like the Eve thigh-high boots by Chloe. Plus, you can style it under chunky knits and outerwear, or over thin jumpers for an effortlessly chic winter ensemble. Finish off your look with the 99 shoulder bag in croc-embossed leather, also by Chloe. You’ll reach for this bag with this outfit and countless others in your closet.

Meanwhile, if you’re head over heels for floral prints (me too) the Rialto silk maxi dress by Loveshackfancy is for you. Use the same styling technique for this dress. Or, pair it with heels and a tailored jacket for best-dressed guest status at every event and winter wedding reception in your calendar. I highly recommend opting for the Giambattista Valli crystal ball pointed-toe slingback pumps and the Secret woven metallic leather clutch bag by Serapin with this must-have dress.

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

  • IRO Miassa Dress

    $295
  • ZIMMERMANN Pleated Puff-Sleeve Tiered Midi Dress

    $725
  • CAMILLA Bias Silk V-Neck Maxi Slip Dress

    $849
  • LOVESHACKFANCY Rialto Silk Maxi Dress

    $765
  • DIANE VON FURSTENBERG Kason Dress

    $548
  • REFORMATION X Kacey Musgraves Bunny Mixed Media Minidress

    $248
  • MAEVE Long-Sleeve Collared Sheer Mini Dress

    $168
  • HUTCH Velvet Shift Bow Mini Dress

    $178
  • MICHAEL COSTELLO X Revolve Gilly Maxi Dress

    $238
  • SNDYS Tahlia Dress

    $87
  • TIARE HAWAII Dahlia V-Neck Ruffle-Sleeve Dress

    $120
  • VERONICA BEARD Isra Silk Dress

  • VERONICA BEARD Seymour Stretch-Silk Dress

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

    $750
  • RIXO Clarice Appliqued Lace-trimmed Velvet Midi Dress

    $360
  • RABANNE Pintucked Embroidered Lace Maxi Dress

    $1,302
  • SIR. Aries Cut Out Gown

    $520
  • DÔEN Rosalinda Floral-Print Voile Midi Dress

    $250
  • LOVESHACKFANCY Manuela Bow Slip Maxi Dress

    $395
  • VICTORIA BECKHAM Gathered Midi Dress Print

    $1,390
  • TOPSHOP Floral Maxi Dress

    $85
  • DÔEN Katarina Dress

    $398
  • DÔEN Oliana Dress

    $498
  • FREE PEOPLE Ultraviolet Dress

    $148

How To Style Winter Dresses With Long Sleeves

When it’s just too cold outside, we need to know how to style winter dresses with long sleeves. If they have long skirts, even better! Luckily, I found dresses like the Kason dress by Diane Von Furstenburg. This colorful silhouette will add a welcome touch of color to any cold-weather lineup. Simply add black boots, like the Garder 45 velvet knee boots by Manolo Blahnik. These boots will match perfectly but allow the print to do all the talking. As will the classic glossed croc-effect leather bag by Tom Ford.

Finally, the Isra silk dress by Veronica Beard will be a staple in your closet for countless seasons, likely years, to come. Simply add brown boots, like the Edrika boots by Isabel Marant to compliment the colorway. Then, accentuate the print with gold details in the print with the Vela small woven bag by Etro.

Shop All Winter Dresses

Relaxed on a dark green sofa, a person wears the DIANE VON FURSTENBERG Kason long sleeve printed maxi dress, featuring abstract designs in yellow, black, and white. Their long hair is pulled back as they gaze to the side with a serene expression, effortlessly demonstrating how to style winter dresses.

DIANE VON FURSTENBERG Kason Dress

A person is elegantly wearing the VERONICA BEARD Isra floral long sleeve maxi dress, featuring a flowing design with long sleeves and a tied waist, perfect for those seeking tips on how to style winter dresses. The dress showcases a beautiful pink and beige floral pattern against a plain white background.

VERONICA BEARD Isra Silk Dress

Luxurious Lunch Date Dress Ideas For Your Weekend Plans