Shoes to Wear with Dresses in Winter: Chic and Cozy Choices

By: Emily Whitehill.

Published on

- 6 min read

Are you tired of trying to figure out which shoes to wear with your dresses during winter? Don’t worry, I’ve got you covered! Winter doesn’t mean you have to stash away your beautiful dresses. Instead, it’s time to get creative with your shoe choices to keep your feet warm and stylish. I’ve experimented with quite a few shoe options over the years, and I’m here to share my top picks for shoes to wear with dresses in winter.

Grey Ankle Boots


Let’s start with a classic: grey ankle boots. These versatile boots work perfectly with almost any dress, from casual to dressy. I love pairing them with a midi dress and tights, which keep me warm and looking chic on chilly days. Grey is also an excellent neutral color that goes with many outfits, so you’ll never feel limited in your choices. Plus, the ankle length gives a nice balance between warmth and style, without overwhelming your look.

When choosing grey ankle boots, consider picking a pair with a comfortable heel height or a slightly elevated platform. This way, you can easily wear them throughout the day without sacrificing comfort. Trust me, your feet will thank you for it!

High Suede Boots

High suede boots can instantly make any winter outfit feel more luxurious. I’ve found that they’re a fantastic option for dressier events or nights out when you want to look extra polished. Pairing them with a knee-length dress can create a sleek and sophisticated silhouette, and the suede material provides an extra touch of elegance.

When it comes to maintenance, suede boots do require a little extra care. I recommend investing in a good suede protector spray to keep them looking their best. Also, consider opting for a block heel or a wider heel for stability on slippery winter surfaces. (Safety first, fashionistas!)

Over the Knee Boots

Over the knee boots are a statement piece in and of themselves. They not only keep your legs warm but also add a touch of drama and allure to your winter outfits. I’ve worn them with shorter dresses and tights or with long dresses that have a side slit, showing just a peek of the boot. The result is always stunning!

When shopping for over the knee boots, consider choosing a pair with a stretchy material or adjustable ties at the top to ensure a comfortable fit. This way, you can enjoy the look without worrying about them slipping down throughout the day. (Nobody has time for that!)

Chelsea Boots

Chelsea boots are a timeless option that can be dressed up or down. Their simple design and comfortable fit make them a go-to choice for everyday wear. I often pair them with a casual dress and tights or even leggings for a cozy winter look.

When choosing Chelsea boots, consider opting for a pair with a rubber sole for extra traction during those snowy or icy days. And don’t be afraid to experiment with different colors or materials - they’re available in everything from classic black leather to fun metallic finishes. (I have a soft spot for patent leather Chelsea boots, personally.)


Who says you can’t wear sneakers with dresses? I’m a firm believer that the right pair of sneakers can make a dress feel fresh and modern, even in winter. I’ve worn my favorite sneakers with sweater dresses, shirt dresses, and even midi dresses for a casual yet stylish look.

When pairing sneakers with dresses, make sure the colors and styles complement each other. I recommend sticking with neutral or monochromatic sneakers for a cohesive look. And, of course, keep those sneakers clean and fresh to avoid looking too casual or sloppy. (A little effort goes a long way, trust me!)


Loafers offer a polished and preppy look that can instantly elevate your winter dress outfits. I find them particularly suitable for work or more formal occasions when you want to keep things classy but still comfortable. Pair them with a tailored dress and tights for a chic ensemble that will never go out of style.

When choosing loafers, consider a pair with a slightly pointed toe for an elongated and elegant silhouette. And don’t shy away from experimenting with different materials, patterns, or embellishments. (A little velvet or a subtle animal print never hurt anyone!)

Studded Boots

For those days when you want to make a statement with your footwear, studded boots are the way to go. They can add an edgy touch to any dress, making your outfit instantly more eye-catching. I’ve worn them with flowy dresses for a fun contrast, or with sleek bodycon dresses for a more cohesive, daring look.

When choosing studded boots, consider the size and placement of the studs, as well as the overall style of the boot. You can go for something more subtle with small, scattered studs or go all out with bold, oversized embellishments. (Rock on, my fellow fashion rebels!)

Flats Shoes

Flats are a timeless and comfortable choice for pairing with dresses in winter. Opt for ballet flats, pointed-toe flats, or even d’Orsay flats for a touch of sophistication. I like to wear them with knee-length or midi dresses, and sometimes I’ll add a fun pair of patterned tights for extra warmth and style.

When choosing flats, consider materials like suede or leather for added warmth and durability during the colder months. And don’t be afraid to play with different colors or prints to add some personality to your winter outfits. (Life’s too short for boring shoes, am I right?)


Last but not least, let’s not forget about the iconic Converse sneakers. These classic kicks can add a fun and casual touch to your winter dress outfits. I love wearing them with mini or midi dresses and tights for a laid-back yet stylish look.

When pairing Converse with dresses, consider sticking to the classic high-top or low-top styles in neutral colors like black or white for the most versatile options. But feel free to explore different colors or even patterned options to let your personality shine through. (You do you, fashionista!)

Winter Wonderland of Shoes: Conclusion

So there you have it, my top shoe picks for wearing with dresses in winter. Whether you’re aiming for a casual, dressy, or edgy vibe, there’s a shoe option for every style and occasion. Don’t let the cold weather hold you back from rocking your favorite dresses. Instead, embrace the opportunity to experiment with different shoe options and make a statement with your winter wardrobe. Happy shoe shopping!