7 Shoes to Wear With Dresses in the Winter
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  • Writer's pictureBrenda

7 Shoes to Wear With Dresses in the Winter

Updated: Nov 10, 2023

With winter literally days away, a lot of you may be thinking it’s time to pack up your dresses until next Spring but I have good news for you: you’re wrong. Dresses can be worn all year long, and this includes during the winter season. It’s a matter of how you style them.

I have talked about how to wear maxi dresses in the Fall and today’s blog post would be similar to that. I would be going over the best shoes to wear with your favorite dresses this winter which would allow you to remain warm, comfortable and stylish.


You can actually look forward to dressing up during the winter months if you invest in the right shoes for the cold weather. You don’t have to stick to your oversized heavy winter boots all the time, even if you absolutely hate the cold. So, if you’re looking for new ways or some inspiration as to how you can create chic winter looks with dresses, do keep reading.

We shall be covering looks you can wear for both casual as well as more formal occasions. Seeing as most people already own several types of dresses these are looks you should be able to re-create using pieces in your wardrobe. You’re about to become a winter fashion style expert by the end of all my winter fashion posts.

Before we hop into the different outfits, I would like to share some great options for websites to find winter footwear which would be great additions to your wardrobe. They would provide sufficient versatility to your wardrobe, allowing you to style them in different ways using various wardrobe items.

*Disclosure: This post may contain affiliate links, which means that I get a small commission if you decide to make a purchase through the links, at no cost to you.

i) DSW

I have repeatedly included DSW on my list of go-to websites to shop footwear. This is because they have a very wide selection of footwear from different brands and designers. In addition to this, a significant percentage of their customers leave reviews and this is very useful when shopping from a brand you’ve never purchased from before.

Their selection of boots is top notch and you’re bound to find a pair for the winter weather. If there’s one pair of boots you should invest in from DSW, it would be Doc Martens Chelsea boots. You can read up some more on styling Chelsea boots via this blog post.

I love the classic look of these Chelsea boots and they feature a leather upper and a cushioned footbed. The reviews would definitely make anyone want to add them to their cart! They could be styled with a pair of skinny jeans or a pencil skirt for a chic winter look.

ii) Nordstrom

If you’re a fan of a taller boot, I invite you to checkout Nordstrom for their wide selection of knee and thigh high boots. These type of boots work well with midi dresses or shorter ones. They cover up more of your leg, providing some extra warmth while giving you a stylish look. I’m especially loving these ones from Michael Kors.

The burgundy colour and gold zipper are just some of the details that draw me to them. They also feature block heels which are more comfortable to walk in for extended periods of time. They would look great with a midi skirt or formal dress.

iii) Lulus

Although Lulus is known mostly for their clothing, they also carry a great selection of footwear at affordable prices. I always check the reviews first before purchasing anything from Lulus and this has helped me have a high satisfaction rate with my orders.

As a fan of some form of color during the colder months, I invite you to try a pair of brown boots instead of the typical black. These tan mid calf boots featuring a faux crocodile upper would be a great option for anyone looking to add some color and detail to their fall and winter wardrobe.

iv) Old Navy

Another website known mostly for its clothing ad nit for its footwear is Old Navy. However, what I appreciate with their selection of footwear is the affordability as well as simple styles. As you’re most likely going to be visiting the site to get a pair of jeans or dress, you might as well check out their shoes section.

I decided to include these penny loafers to my list because on those days you want to change into a different type of shoe upon arrival at your destination, they would be a great choice. They seem to be selling out quickly so I would hop on them ASAP.

Now that we’ve talked about some great websites to find some great shoes to style with your dresses during the winter, let’s go through the different shoe and dress combinations that could work. These looks should work for any body type and can be created using pieces you most likely already own. Here are my favorite shoes to wear with dresses when it’s cold outside.

1) Knee boots

Knee-high boots are a great option to go with if you’re opting for a shorter dress or a midi one. You could definitely wear them with a maxi dress, but I find if your dress is that long, you would just be hiding the beauty of your boots. We want to show them off! If your dress is in a bold color or features bold prints, opt for a pair of boots in a neutral color such as brown, black or white.

Get the look HERE

You could add a pair of black tights or leggings underneath your dress to add an extra layer of warmth. Also choose knee boots when styling your shorter sweater dresses. More about that on my post on how to wear a sweater dress. Headed to a farm wedding during the winter, go for a pair of cowboy boots and a midi dress.

2) Heeled ankle boots

A heeled ankle bootie goes a long way during the winter months. I would say they are the best shoes to style with jeans and have now made their way to this list as well. Opting for a heeled bootie makes your look dressier and so opt for these when you’re putting together outfits for formal events. You could pair a maxi dress with long sleeves and a pair of sleek white ankle boots for a winter wedding look.

Get the look HERE

This is a good choice if you’re avoiding a strappy sandal due to the cold and snow on the ground. This also works with a maxi skirt, making your ankle heels a great versatile shoe.

3) Over-the-knee boots

A pair of tall boots can make your legs appear longer and that’s why you want to style them with your shorter dresses. If your boots hit you right where your dress ends, it could create the illusion of longer legs. Create a chic look that could take you from the office to happy hour by adding your floral mini dress to your thigh-high boots, wearing a pair of thermal leggings underneath and throwing on a leather jacket or lined coat.

Get the look HERE

You would be able to stay warm yet stylish in this outfit. Over the knee boots also work well with short sweater dresses and skirts and provide some much-needed warmth on your thighs. For a more captivating look, go for the heeled OTK boots and watch the heads turn.

4) Flats

For my ladies who really just love to wear flat shoes year round, I would say you could pull them off if you’re commuting from the comfort of your car or if you’re changing into them upon arrival at your destination.

You could style a casual look by pairing one of your summer maxis with a pair of flats. One of my favorite ways of wearing my maxis during the winter is by wearing a sweater on top as descried in my blog post here.

Image source here

This is a look you could even wear at the office if it has a business casual dress code in effect. You could also wear a pair of flats with a maxi to a formal event, just make sure the ballet flats are sleek. Perhaps with a little bling.

5) High heels

I think it’s pretty common knowledge that high heels are a great shoe to wear to formal events. Although it’s cold outside, sometimes you really just want to throw on a pair of heels with that cute formal dress. Think of all the holiday parties you plan on attending. You could even opt for a pair of kitten heels if you’re concerned about heel height.

Get the look HERE

Pair your long dresses with heels and make sure to ask that Uber driver to pull up all the way to your door.

6) Combat boots

The best way to add a casual vibe to your winter dress outfits is by opting for a pair of combat boots. You could pair them with short dresses, a pair of black tights and a sweater on top. You could also pair the boots with a shirt dress and black leggings to recycle your shirt dresses. Combat boots such as Doc Martens are also a great choice of footwear for a rainy day.

Get the look HERE

Another way to style them is by wearing a sweater underneath a slip dress and throwing on a black leather jacket. This is such a popular streetwear look you could recreate with midi summer dresses during the cold months.

7) Flat ankle boots

Flat ankle boots are a winter wardrobe essential thanks to their versatility. You could pair them with midi dresses or a midi skirt for a comfortable, warm and sophisticated look. If you’re not up to throwing on a pair of heeled ankle boots, then go for these.

It is true that you could also pair them with dress pants for a winter corporate look but there’s no reason why you can’t wear a sleek pencil dress with a pair of black ankle boots for an equally powerful boardroom look. Flat booties could also be worn with oversized sweaters and sweater dresses for more casual occasions.

Image source here

I certainly hope you have gotten some great style ideas for the next time you’re wondering how to wear your dresses in the winter. The type of shoe you go with only depends on the dress code and they dress you’re opting for. I have provided you with some good options which can serve as a guide. Let me know which was your favorite.

If you enjoyed this post, you should definitely check out my post on how to wear brown boots.

I also have a post on how to wear a poncho sweater, which is a great winter wardrobe piece!

About to experience winter in Chicago? Check out my post: Your Guide on WHat to Wear and how to Survive a Chicago Winter.

If you're wondering which dress shoes to pair with your work pants in the winter, check out my post: 11 Shoes to Wear with Dress Pants in the Winter.

Wondering what shoes to pair with your maxi dresses in the winter? Check out my post: The 13 Best Shoes to Wear with a Maxi Dress in the Winter.

For those looking for inspiration when it comes to pairing a coat with a dress, check out: the 7 best coats to wear with dresses.

Until the next post,



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