What Shoes to Wear with a Dress in Winter?

You can still rock your dresses, even in winter! The right pair of shoes can keep you warm while making your outfit look effortlessly chic. Whether you’re heading to work, a casual outing, or a special occasion, knowing what shoes to wear with a dress in winter is key to balancing comfort, warmth, and style. Let’s dive into the best footwear options for winter dresses, from ankle boots to knee-highs and even sneakers.

8 Best Shoes to Wear with a Dress in Winter

1. Ankle Boots – The Versatile Essential

Ankle boots are a winter staple and work with just about any dress. Whether you’re going for a casual look or something more polished, these boots get the job done.

How to Wear Them:

• For an effortless everyday look, throw on flat or block-heeled ankle boots with a sweater dress and a cozy scarf.
• If you’re dressing up, pointed-toe ankle boots with a flowy midi dress create a sleek, sophisticated outfit.
• Don’t forget tights or fleece-lined leggings when the temperatures drop—they add warmth without compromising style.

2. Knee-High Boots – Elegant and Cozy

Knee-high boots effortlessly merge comfort with elegance. They elongate the legs and add an effortlessly chic vibe to winter dresses.

How to Wear Them:

• A bodycon dress and knee-high boots create a sleek and put-together outfit.
• For a more relaxed look, pair them with a loose-fitting sweater dress and a belt at the waist.
• Add a long coat or structured blazer to pull the whole look together on colder days.

3. Combat Boots – The Cool-Girl Choice

Want to add a bit of edge to your winter dresses? Combat boots are a must-have for any edgy style. They offer comfort, longevity, and a naturally stylish touch to your outfit.

How to Wear Them:

• Pair combat boots with a floral maxi dress for a trendy contrast between feminine and edgy.
• A turtleneck sweater dress and combat boots create a stylish yet practical winter outfit.
• To complete the look, add a leather jacket and a beanie.

4. Sneakers – The Ultimate Comfort Option

Yes, you can wear sneakers with dresses in the winter! They keep things casual and comfortable while adding a modern touch.

How to Wear Them:

• A midi sweater dress with white sneakers is effortlessly stylish.
• Try chunky sneakers with a hoodie dress for a sporty, cozy outfit.
• If it’s extra chilly, layer up with thick socks and an oversized coat.

5. High Heels – For Special Occasions

Sometimes, you just need a little height! Heels instantly elevate any winter dress outfit. The key is choosing closed-toe or block-heeled styles to keep things practical.

How to Wear Them:

• A wool midi dress with classic pumps is perfect for a polished winter look.
• Block-heeled booties offer both style and stability—great for date nights or formal events.
• Suede or velvet heels add a seasonal touch and look great with any dress style.

6. Over-The-Knee Boots – Statement-Making and Warm

Over-the-knee boots make a strong fashion statement while keeping your legs warm. Perfect for mini and midi dresses alike!

How to Wear Them:

• Style over-the-knee boots with a turtleneck sweater dress for a sleek winter look.
• For a bit more drama, wear them with a short, flowy dress and a long coat.
• Choose suede or leather materials to add texture and a luxe feel.

7. Mid-Calf Boots – The Underrated Hero

Mid-calf boots don’t get enough credit! They’re stylish, and practical, and work well with different dress lengths.

How to Wear Them:

• A ribbed knit dress and mid-calf boots make for a cozy, trendy winter outfit.
• Pair slouchy mid-calf boots with a bohemian maxi dress for an effortlessly chic vibe.
• A structured leather boot pairs well with fitted midi dresses and layered outerwear.

8. Can You Wear Snow Boots with Dresses? Absolutely!

Snow boots might not be the first thing that comes to mind when styling a dress, but with the right approach, they can look just as fashionable as they are functional.

How to Wear Them:

• Fitted sweater dresses with fur-lined snow boots create a cozy yet stylish winter outfit.
• A puffer coat over a knit dress balances warmth and fashion.
• Stick to neutral-colored snow boots to keep the look streamlined and stylish.

Final Thoughts – Stay Warm, Stay Stylish!

Winter dressing is all about balance—you want to stay warm without sacrificing style. Whether you’re rocking combat boots for an edgy look, knee-high boots for elegance, or sneakers for everyday comfort, there’s a perfect winter shoe for every dress in your wardrobe. Layer up, experiment with textures, and have fun with your winter style!