Here’s Everything to Style with Winter Dresses

Getting dressed in a cold-weather outfit to face ice-cold temperatures can be challenging. Multiple layers of clothing are often involved: Jeans shimmied over thermal pants or T-shirts and long-sleeve base layers shoved under sweaters. There’s so much involved that you might need to pause and catch your breath after assembling your outfit. But there’s a more straightforward, streamlined solution to getting dressed for the elements. I’m talking about the best winter dresses that practically style themselves.

Style a great dress with the latest boot trends and a warm jacket or coat, and you will have a foolproof blueprint for a capsule wardrobe collection.

I’ve handpicked various street-style-inspired winter dress outfits, from casual knit styles that you can pair with teddy coats and sneakers to upscale satin dresses that look great with sleek blazers and heels. Scroll on to shop from brands like Theory, J.Crew, Banana Republic, and more.
Yes, you can wear a mini dress in the dead of winter. Simply style it to offer enough coverage—thigh-high boots and a durable leather trench coat should suffice.

Apparis Tate Trench

$575 at Revolve

Ser.o.ya Lauren Mini Dress

$158 at Saks Fifth Avenue

Madewell The Dimes Over-The-Knee Boot

$348 at Madewell

Oh So Sweet

Chocolate brown will dominate the color trend cycle in 2025, so incorporate it into the look with a luxe winter dress in the shade. Add embellishments like a designer belt, slouchy boots, and an edgy, 80s-inspired bomber jacket.

Maje 2-In-1 Wool Maxi Dress

$375 at Saks Fifth Avenue

Aritzia Synergy Bomber

$228 at Aritzia

Saint Laurent Cassandre Belt Bracelet in Leather

$350 at Saks Fifth Avenue

A Winning Color Combination

Are you looking for a way to elevate a classic black dress? Consider accessories drenched in warm shades of mulled wine. The black-and-burgundy color combo is unmatched.

Theory Turtleneck Wool-Blend Pleated Sweaterdress

$375 at Saks Fifth Avenue

8 Other Reasons Emily Shoulder Bag

$129 at Revolve

Jeffrey Campbell Botas Distant-Hi Boots

$204 at Revolve