These Are the Winter Shoes You'll Be Wearing With Your Dresses

Dresses are one of the most versatile clothing pieces you could own. That's why, when winter comes along, you shouldn't discard them right off the bat. Instead, you need to get creative and tap into that versatility because not only are they highly useful, but they always look great. Whether wearing an oversize sweater over your favorite maxi dress so it becomes a faux skirt or styling a midi dress over pants for extra comfort and much-needed warmth, there are so many ways to give more life to your dresses during the colder months.

However, when it comes to what shoes you're going to be pairing with your dresses over and over again, there are handfuls that come to mind but all of them might not be winter-friendly. We too want to wear slides and heeled sandals year-round as much as the next guy, but we also value our toes and would like to keep our limbs intact.

To find out our chosen winter shoes to wear with dresses, read on. From classic black ankle boots to some awkward-length boots we’re swooning over, the boots, sneakers, and even mules ahead will make you start outfit planning pronto.

Tall Boots

Not exactly knee-high boots or ankle boots, tall boots fall awkwardly on your calves or a little bit under your knees. This tall silhouette makes them perfect to style with all your midi dresses.

Because everybody needs more leopard print in their lives.

Say hello to our current favorite Western-inspired boot. 

These will look great with all your dresses. 


Sneakers are seasonless shoes. It's a no-brainer that they made our list. Whether you pair them with really chunky socks or cute trendy ones, they will make your dresses look casual yet chic. 

Ask NYC girls about their fave kicks and they will all say it's their Nike Air Force 1s.

Sometimes you just need a red pair of sneakers. 

Ankle Boots 

Ankle boots are a must when it comes to winter shoes. Because whether with kitten heels, block heels platforms, or even flat soles, they will make your ensemble look effortless. 

Perfect to pair with all your prairie dresses. 

Can you believe these are from H&M? 

Just in case you need yet another pair of black ankle boots. 


Contrary to popular belief you can indeed wear mules during the winter. Simply stock up on some good tights and socks that will add texture to your outfit. 

Style and comfort all in one. 

Slightly different than white boots but just as good. 

Now that you have your shoe-and-dress combo settled, it's time to think about what shoes you can wear with your leggings (besides sneakers). 

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