What Shoes To Wear With Dresses In Winter

When it comes to dressing up, you want to ensure you’re comfortable. However, if the temperature outside isn’t cooperating, it might be hard to find the perfect outfit. In this article, you’ll find some tips on how to pair shoes with dresses in winter and still look great!

The right shoes can make all the difference when dressing for winter. While it’s nice to have a closet full of boots, they’re not always the best choice — especially if you’re wearing a dress or skirt.

What Shoes To Wear With Dresses In Winter

Here are some tips to consider when it comes to wearing shoes with dresses in the winter

  • Consider your dress’s hemline

Consider how much leg you want to show when choosing heels for winter dresses. If you’re wearing a midi or maxi skirt, then high heels are probably not the best choice.

Instead, opt for flats or booties with ankle straps that keep your feet warm and prevent them from getting wet in the snow and rain.

  • Match your shoes with your outfit

When picking out heels for any occasion, make sure they match your outfit as well as possible, so you don’t clash with yourself.

For example, if you’re wearing a pair of black tights and brown boots, stick with black heels; this way they’ll blend in with everything else on your body without distracting from the rest of what you’re wearing.

  • Color

Black is always a good color choice in winter because it can be worn with everything else in your closet without looking out of place.

However, if black isn’t your thing, try going for neutral colors like brown or gray instead of bright colors like red or yellow, which can easily rub off on white snow!

  • Think about comfort

If your shoes aren’t comfortable enough for you, they won’t help keep your feet warm! It’s important to find shoes that fit well and feel good on your feet so that they don’t hurt after just a few minutes of wear.

This can be especially important if you’re planning on wearing them all night long while out dancing or partying at bars or clubs with friends!

12 Best Types of Shoes To Wear With Dresses In Winter

Boots – For those that don’t want to wear boots, there are plenty of options. Another excellent choice is a pair of tall socks and loafers or flats for winter weather.

These can be worn with everything from a maxi dress to jeans, providing an extra layer between your skin and the cold ground.

While this might seem an obvious option, many people forget about it when searching for shoes to wear with dresses in winter!

If you plan on being outdoors in snowy conditions and need more than just a pair of wool socks, I recommend boots!

Boots are the best footwear choice if you live somewhere where there is snow (or even worse: ice) on the ground throughout most winters.

They keep out snow as well as rainwater so that your toes stay dry throughout any unexpected downpours;

However, they are heavier than other types of shoes, which means if you plan on wearing them all day long, then make sure you have some comfortable insoles inside them before wearing them out on long walks around town or anything like that.

1. Ankle Boots

Ankle boots are an excellent choice for winter since they can be paired with dresses and pants.

They look great with tights, socks, or even bare legs, depending on the cold outside.

Ankle boots can also be worn with sweaters and jackets for extra warmth during the colder months of winter.

2. Combat Boots

Combat boots are a great choice if you’re looking for the best shoes to wear with dresses in winter. They’re great for standing up to the elements and keeping your feet warm and dry.

Combat boots come in ankle-high and thigh-high varieties, so you’ll have no problem finding the perfect pair for your new dress.

The best part about combat boots is that they look great with any outfit. You can wear them with jeans, leggings, or even a skirt if you want something more feminine.

Combat boots are versatile enough to be worn year-round, so there’s no need to buy another pair of shoes when it gets warmer. Just switch out your socks!

3. Lace-up Boots

Lace-up boots are a good option for pairing with dresses in the winter. They are both practical and comfortable and come in various colors, materials, and styles.

The best lace-up boots for wearing with dresses are those with a thick soles that will keep you warm on cold days, but if your feet get too hot or uncomfortable, remove the insoles from those shoes before putting them on.

4. Cowboy Boots

Cowboy boots are stylish, comfortable, and versatile. They can be worn with dresses, skirts, jeans or trousers. You can wear them to work or out on the town.

They’re great for walking in the snow and suitable for wearing in winter.

5. Faux Fur Booties

A pair of faux fur booties are the perfect way to add warmth and style to your outfit.

The best thing about these shoes is that they come in various colors so that you can find the perfect pair for your personality and wardrobe.

6. The Thigh-High Boots

The thigh-high boots are an ideal shoe to wear with dresses in winter because they will keep your legs warm while offering a stylish look.

You can wear thigh-high boots with various outfits such as dresses, skirts, or pants.

They will ensure that you look chic without worrying about getting cold feet in cold weather conditions.

7. Loafers and Oxfords

If you want a sophisticated look that goes beyond just jeans, try pairing your dress with a pair of loafers or oxfords.

These classic shoes are great for any occasion and can be worn with any dress. Loafers are especially versatile because they come in many different colors and styles.

You can find loafers in suede, leather, or canvas fabric; they come with open toes or closed heels; some have buckles, others feature elastic laces, some are plain, while others feature embroidery or other embellishments. The possibilities are endless!

8. Block Heels

Block heels are perfect for dressy occasions or when you want to look more formal with your outfit.

They’re not too high so that you won’t be wobbling around like an idiot, and they’re also not too low, so they don’t make your legs look shorter than they already are (hello kitten heels).

And if you’re not into heels at all, platforms are available that give a bit more height without making your feet sore after walking around in them all day!

Plus, if you get them in suede, they can double as casual boots, too, since suede is such a popular material this season!

9. Pumps or Heels

These are the most versatile shoes that go well with dress outfits.

Pumps and heels can be worn with different lengths of dresses, and they will look good no matter your dress’s color.

They also come in many different styles, so there is something for everyone!

10. Sneakers

Sneakers are one of the most versatile pieces of footwear for women, especially during the chilly months.

They are perfect for wearing with dresses because they can be dressed up or down based on how you accessorize your outfit.

Sneakers come in many different shapes, sizes, colors, and materials.

You can find flats made from leather or suede, synthetic materials like vinyl or faux leather, canvas, or linen.

They work well with dresses of all lengths and styles, so you don’t have to worry about finding a pair that’s the right match for your dress.

11. Wedge Boots

Wedge boots are a great type of shoe to wear with dresses in winter. You can wear them with either casual or formal attire, depending on the occasion.

You can choose from a variety of colors like brown, black, and nude shades. This will give you an option to match your wedge sandals with your dress color.

The wedges come in different styles such as peep toes and open backs as well.

These shoes give you more comfort as they have cushioned insoles that provide extra support to your feet while walking or standing all day long!

12. Mary Janes

Mary Janes are one of the most versatile shoes you can own. They’re perfect for wearing dresses because they go with almost anything! Plus, they’re not too high, which makes them perfect for wearing all day long.

Mary Janes come in a variety of styles and colors, so there’s no shortage of options to choose from.

For example, you can find Mary Janes that are made out of leather or suede, which will give your outfit a more dressy vibe.

If you’re looking for something more casual, then you should consider purchasing Mary Janes in suede or leather with tassels on top.

These types of Mary Janes are great for wearing on cold days because they’ll keep your feet warm and cozy!

If you want to wear your Mary Janes with dresses in winter, then make sure that you have at least one pair of black ones in your closet.

Black is the perfect color for wearing with any outfit – it goes with everything! You can also opt for tan or brown versions if you want to add more color to your dress.


There are so many shoes to choose from, which can sometimes be overwhelming.

But as you can see from our list, there are plenty of options you can go with if this is something you’re looking into doing. We recommend trying all these styles and seeing what works best for you!

Dresses & Cold Weather Related Articles:

What to Wear Over a Formal Dress When Cold

How to Wear a Maxi Dress in Winter

What Shoes to Wear with a Maxi Dress in Winter

What Shoes to Wear with a Maxi Dress in Fall