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.

Hiked-Up Hemlines

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.

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.

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.

The Cozy Agenda

Although often worn for high-end occasions, a winter dress can totally lend itself to laid-back moments. For your next errand run, wear a snug slip-on dress with a fuzzy teddy coat and cushioned sneakers.

All Dressed Up

Master the cocktail attire dress code with a sumptuous satin or crepe dress styled beneath a blazer. Wear a faux fur coat or even a Yeti coat that embodies the beloved mob wife aesthetic if you need an additional layer.

Follow the It-Girl Lead

The street-style scene champions the loafers-and-socks hack, great for pairing with dresses. It’s straightforward, and most importantly, it feels refreshingly versatile.

Living Large

There’s something about this style maven’s lustrous leather coat and luxe knit dress that radiates wealth, falling into the rich-looking outfits category. The polished sunglasses, gold jewelry, and designer handbags also feed into the expensive vibe.

A Fusion of Fabrics

Despite what some might say, you can still make a statement with neutral colors. The key is to blend in different fabrics like silk and wool. Take things a step further with a pair of knee-high boots plastered in suede.

Late-Night Look

For your next evening outing, take a figure-hugging dress for a spin. Complete the look with a floor-sweeping cream coat and a pair of slingback heels, and this getup will become your new going-out outfit.

Nice and Toasty

There’s a common notion that dressing up means sacrificing comfort for style—but it doesn't have to be that way. Pair a winter dress with an oversized cardigan that feels like a blanket. Then, swap your heels for a pair of flat moto boots that are made for walking.