How to Pair Boots With Dresses – 2024 Guide

Some fashion combos never go out of style. Pairing dresses and boots will forever be a favorite for a lot of people. This is a great combination that can look casual, smart and official, but also elegant. The best thing about this outfit is that it requires minimal effort. All you need to do is find a beautiful dress and matching boots and you are ready to go.

Next time you go shopping have this combination in mind. If you don’t know what works well together, we’ve come up with some combinations that can really fit. Keep reading to learn how to wear dresses with boots and find out what the most popular combinations are.

1. Styling for the Occasion


First of all, you need to find a pair of boots that will go well with the dress you are wearing. However, you also need to consider the occasion. Is it a formal evening, a dinner, or you are just going out with some friends?

Based on this, you can think about what to wear. For example, motorcycle boots don’t go well with a light flowing dress. If you insist on wearing motorcycle boots, you should combine them with the leather dress, preferably shorter. On the other hand, a flowing dress in light colors go well with brown ankle boots.

2. Thigh-High Boots vs. Ankle Boots

Depending on your preferences, you can either choose thigh-high boots or ankle boots. The thigh-high boots are perfect if you are going to a more formal event and they don’t look good in a casual setting. On the other hand, ankle boots are more laid back and they are better in a more casual setting.

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Of course, you can wear ankle boots to a formal event too. There aren’t rules against it, especially if we are talking about stylish boots. Just make sure to find the right pair.

3. Bare legs or tights?


Another choice women often have is whether to have bare legs or wear tights. There isn’t a definitive answer here and it mostly depends on the weather. If it is hot outside, you can wear some casual boots with a short dress and have bare legs.

However, if it is cold outside, you need to dress up. Wearing a dress with some tights is still a possibility, but in that case, we recommend faux leather riding boots instead of the ankle flats. You need to cover up so you aren’t feeling cold.

4. How much to show?

Unless it is cold, you should have a portion of your legs showing. If you are wearing shorter dresses and longer boots, then your needs can remain visible and a small area around your knees. On the other hand, you can always show more with shorter boots. Leaving a few inches exposed really looks stylish, but this has to be tasty.

Shorter dresses allow for more combinations as they are more versatile and you will feel more comfortable wearing them.

Now that you know some basic principles of combining boots and dresses it is time to check some combinations. If you are looking for any kind of boots that you want to pair with your dress, you can always visit

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Lug Sole Boots and Slip Dresses


If you are going for a retro outfit, you may consider heavier boots in combination with a silk slip dress. One of the benefits of this combo is that it can be perfect for warmer leather, but you can also add layers and wear it during the winter as well.

Western Boots and Nap Dress


This combination just works well together, but it isn’t for everyone. If you love to experiment a bit and you want to go with that Western look, wearing western boots with nap dress is a perfect way to go. This can be a casual outfit which you will use during the day, especially if the nap dress is a bit shorter.

Not everyone finds this look appealing, but it is nice to change things up from time to time and get out of the ordinary styling combinations.

Swing dress and over-the-knee boots


The swing dress is just right for every woman. It is a casual wear, perfect for summer weather, with bright and happy colors. The dress will make you feel comfortable and at home. When it comes to the boots, there are various combinations here, but one that stands out is the swing dress + boots that go over the knees.

The tick is to keep the boots as simple as possible. They should be with a minimalist design. While the boots are supposed to attract the attention, they don’t want to steal all the looks away from the dress.

Neutral boots and Pastoral Prints


In case you want a colorful and jolly outfit you can choose a spring dress with flower design. This type of dress requires something more neutral and simplistic, which is why neutral brown boots with a moderate heel is the best choice here.

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Printed Boots and Shirtdress


There are so many dresses which are stylish and elegant but something that’s been really popular lately is the shirtdress. This is basically a dress that looks like a shirt and it really shows that you have a great fashion taste. With this type of a dress, that usually comes in white you can pair some printed boots. As long as the uniform is in one color, you can carry out printed boots and still look lovely.


Wearing boots with a dress comes naturally and there are so many combinations which you can choose from. At the end of the day, it all depends on what you want to wear and what the occasion is. We recommend that you try out different combinations and see what fits and what makes you feel great!