The 10 Most Comfortable Shoes to Wear with Dresses - (2024)

Summer is here, so it is time to choose the comfortable shoes to wear with your dresses. Skirts and dresses are some of the most feminine and bohemian clothing items in a woman’s wardrobe.

However, when choosing the shoes that go with dresses, you often think that it is hard to find shoes that are both stylish and comfortable. Most types of footwear on the market today are not very comfortable and also not too healthy for the feet.

The 10 Most Comfortable Shoes to Wear with Dresses - (1)

According to a study conducted in America, over 50% of Americans between the ages of 18 and 60 suffer from a foot disease, and this is only due to the fact that they wear inappropriate footwear. Therefore, you should rely on comfort when you wear shoes.

Table of Contents

  • Here is a list of the 10 most comfortable shoes that you can easily combine and wear with dresses:
  • Final thoughts on the most comfortable shoes to wear with dresses

Here is a list of the 10 most comfortable shoes that you can easily combine and wear with dresses:

  1. Sneakers
  2. Canvas shoes
  3. Flats
  4. Sandals
  5. Cowboy boots
  6. Moccasin
  7. Platform sandals
  8. Espadrilles
  9. Oxford shoes
  10. Knee Boots


This type of footwear is the most popular. It comes in many sizes, shapes, and styles.

You can wear chunky sneakers, which are one of my favorites, slip-on sneakers, plimsoll sneakers, authentic sneakers, and the list goes on. Even if they may seem like they are too casual and don’t go well with a dress, think again.

If you have a floral summer dress and want something that is comfortable for a whole walk in the park, then you cannot go wrong with a white pair of sneakers.

It also goes great with a longer dress, a shirtdress, or even a slip dress. You should not punish your feet just because of fashion. Offer them the proper footwear to take you anywhere you want to go.

Canvas Shoes

The canvas shoes are again very popular. They go with everything, from jeans to skirts, to dresses.

They are very light and flexible and that is what makes them so comfortable. What distinguishes them from other types of footwear is that the upper part at the beginning of the shoe is made of rubber and is usually white.

The rest of the shoe is made of cloth or a synthetic mix. They can go until your ankle or above it, depending on the style you choose. They come in different colors and go great with everything.

You can combine them easily with multiple types of dresses, such as A-line dresses, asymmetrical dresses, camisole dresses, and so on. You cannot go wrong with this footwear.


A must-have piece in every woman’s wardrobe. Not only are they very comfortable, easy to wear, and versatile, but they are also very stylish and they come in thousands of designs.

Flats are a type of footwear that have no high heels and that expose the top of the foot. They are usually made of leather or leather substitutes, which is what makes them so comfortable.

The front of the shoe can have different shapes and can be closed-toe or not. They can have shoe straps or not.

The designs available for this type of footwear are unlimited, as well as the colors. It is no doubt that they go great with dresses, creating a very chic and feminine outfit, which is perfect for summer nights.


Summer is here so you know what that means: sandals! They are light shoes that usually have an open-end toe and that have straps attached to the sole of the shoe.

They are usually made of leather or a leather substitute and are as comfortable as flats. You can find an infinite number of designs again.

My favorite would be toe sandals and gladiator sandals. Toe sandals are a type of design in which the straps come between the big toe and second toe, just like with flip-flops.

Gladiator sandals have many straps on the foot, but they also have long straps that can be tied up on the leg, just like the footwear of ancient Roman gladiators.

They go great with every type of dress. My favorite combination is the balloon dress with gladiator sandals because they highlight your legs, making them longer.

Cowboy Boots

Out of all the types of footwear that exist, these are my favorites. A stylish, chic, and gorgeous pair of cowboy boots will never go out of style.

They are a high-heeled boot with a pointed toe and stitches on the vamp, which is the front part of the shoe, and on the shaft.

They also have pull straps located on each side of the very top of each cowboy boot, so that you can easily pull them.

They are mostly made of leather, making them the most comfortable high heels you will ever wear. The shaft of the boot usually reaches mid-calf, but they can be longer or shorter, depending on the design.

They go great with A-line dresses, asymmetrical dresses, or smock dresses. I wouldn’t pair them with a more formal type of dress, such as a pencil or a blazer, since they are a casual type of footwear.


This type of footwear is very chic and elegant but above all comfortable. They are a style inspired by the North American Indians and are made of soft leather, without heels.

The sole and sides of the shoe are brought together in the front of the shoe and stitched together in a gathered seam.

The soft leather hugs your feet, making them very comfortable for everyday activities; just make sure you find the right fit for you.

They come in different colors, but the most popular are brown and black. They are very practical and casual, pairing perfectly with many dresses.

Platform Sandals

For the lovers of heels, but whose feet don’t resist too much, this type of footwear is perfect. Just as the name suggests, they are sandals with a platform that goes on the entire sole.

The platform can have different heights, so I suggest you choose one that is the snug fit for you. They can come in different styles, designs, and colors, just like sandals.

Any type of dress goes great with these sandals. They go great with casual dresses (A-line, apron, blouse dresses, and so on) but also with more formal ones (balloon, pencil, blazer dresses), all thanks to the many designs that are out there.


Espadrilles are sturdy and comfortable. They are made of canvas, with a sole made of rope.

They have a closed-toe and a closed-back and without heels. They can also have a smaller closed-back, with lacing straps that go up on the leg.

If chosen properly, they can be very comfortable and your feet ‘breath’. Just slip your feet in and you are good to go.

Many designs and colors can be found for espadrilles, but the most popular ones are blue and white stripes. They go great with casual and semi-formal dresses and are perfect for a stroll.

Oxford Shoes

This type of shoe is traditional in the UK. They were initially created for men, but they eventually became very popular amongst women.

The leather material from which they are made makes them very comfortable and easy to wear. The shoelaces that can be found beneath the vamp help you tighten them as tight or wide as you want.

They can be found in many colors, but the most popular ones are the classical ones, which are black or brown and simple.

They are chic and timeless and used to be a statement in the academic world, so I recommend you pair them with more formal dresses, such as a blazer dress or pencil dress.

Knee Boots

A great and very elegant type of footwear. They are boots that go up till your knee or above it.

They can be made of leather, substitute for leather, rubber, or a combination of materials. Make sure to try them on to see if they are comfortable.

Many boots may be very elegant and beautiful, but they don’t get along with your feet. The designs and colors are infinite: you can have laces or not, you can have zippers, or you can simply slip them on. They can also have high heels or not.

I find the ones without heels to be more comfortable. You can wear them with almost every type of dress: from A-line, to minis, to pencil and blazer dresses. Just pay attention to the color and the pattern on them.

Final thoughts on the most comfortable shoes to wear with dresses

When you think of the most comfortable women’s dress shoes, don’t stop at flats and sandals.

These are not your only solutions. There are a lot of types of shoes that are ready to take care of your feet and also add glamor to your outfit.

Whether it’s cowboy boots, moccasins, sneakers, and so on, these shoes will help you create a great and stylish outfit.

The material of the shoes is a really important factor in your decision.

When you buy your shoes, you should first rely on comfort, so that you can enjoy healthy feet as well as a pair of shoes that are as comfortable as possible to make walking more comfortable.

Remember that the most important aspect is that your feet are happy. Take care of them by choosing one of these 10 types of comfortable shoes.

The 10 Most Comfortable Shoes to Wear with Dresses - (2024)


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