How to Wear Riding Boots with Skirts

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The perfect way to achieve a horsewoman style while still maintaining a feminine look is to pair riding boots with a skirt. This style shows that you are still in touch with your girly side no matter how far you try to adventure.

Equestrian boots never go out of fashion so a good pair of these boots paired with different skirts will always be timeless in your wardrobe. No matter your style, there are countless ways to pull this look.

Let me show you different ways of wearing riding boots with skirts.

7 Different Ways on How to Wear Riding Boots with Skirts

 1. A-line midi skirt paired with shorter boots

An A-line midi skirt with shorter boots is an awesome combination. Since the skirt goes below the knees, you need to wear ankle-length boots or mid-calf boots so that you leave some space to show your legs.

Midi skirts are trendy and wearing them with shorter horse riding boots reflects your fashion-forward side. This can be a great look for Sunday brunch or can even be a work outfit depending on your workplace culture. It is a comfortable look so you can wear it anywhere and anytime.

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EXCHIC Women's Casual Stretchy Flared Mini Skater Skirt Basic A-Line Pleated Midi Skirt. One of the best skirts for pairing with equestrian riding boots

2. Shorter skirts with knee-high boots

If you are looking for a sexy look, you better pair a shorter circle skirt with knee-high boots. The skirt should hit above the knees so that you leave a little space to expose your legs. And you’re not limited here: you can decide to go for a tight-fitting skirt or a flowy one.

By the way, this is a perfect look for a night out with the girls or even a date. It gives a young vibe so if you want to feel young and vibrant, this is the look to go for.

HDE Women's Casual Fashion Flared Pleated A-Line Circle Skater Skirt. One of the best skater skirts for matching with knee-high boots

3. Pair close-fitting or stiff skirts e.g. denim, with tights or leggings

Close-fitting skirts or stiff ones such as leather and denim go well with tights and leggings. This style is ideal for the colder months and it is also great if you want to look a little bit modest without compromising your style.

If you are going to wear a short denim or leather skirt with tights, pair them with calf-length boots. This is a good weekend or casual look when the weather starts getting cold. The boots and tights provide extra coverage to keep you warm while maintaining a stylish vibe.

4. Breezy or flowy skirts should expose a part of the legs

Wearing breezy or flowy skirts with boots can be tricky. Since a lot is going on with the skirt, your riding boots might get lost in the outfit. If you’re wondering what to wear with riding boots to avoid looking over-styled, the trick is to make sure that you reveal a sliver of leg skin if you choose this combination.

For instance, if you go for a mini flowy skirt, opt for high boots that leave some space for your legs. On the other hand, if you go for a midi flowy skirt, go for shorter boots to flatter your lower legs and prevent a masculine look. This is a balanced look ideal for casual settings.

5. Pair flowy skirts with a slim-fit turtleneck top

You already know that you can wear a flowy skirt with your boots. However, pairing your skirt with a slim-fit turtleneck top is the best way to balance the masculinity of the boots and your femininity.

Since the skirt is already flowy, the best way to balance your style when wearing tight-fitting riding boots is to wear a slim-fit turtleneck top. Turtleneck tops are timeless and can be worn by women of all age groups so you can never go wrong with one.

6. Slip a blazer, sweatshirt, or sweater over your shirt or top, depending on the weather and occasion

How to Wear Riding Boots to Work

Riding boots are perfect for the cold months. If you want to make them look more workplace-friendly, you can wear a blazer to achieve a business casual look.

For a laid-back look, you can opt for a sweater or sweatshirt depending on your preference. Riding boots, a pencil skirt, and a blazer is an awesome combo that will keep you warm any day.

If you're wondering how to wear riding boots with skirts, or how to wear riding boots to work, here is a solution. SweatyRocks Women's Business Suit 2 Pieces Tweed Blazer Jacket Coat and Pencil Skirt Set matched with knee-high riding boots

7. Wear skirts with beautiful prints to match the plain boots

When it comes to wearing skirts with boots, do not be afraid to explore and experiment. You do not have to wear a boring plain skirt with your riding boots.

Try different prints, textures, and patterns to see what you can come up with. Since most boots come in plain colors, it will help to go all the way with your choice of skirt colors and patterns. You will be surprised by the look you can pull by trying out different prints.


Skirts and horse riding boots are a perfect combination. There are many ways to pair these two items depending on your style, age, and occasion. Riding boots will always be timeless so pairing them with different types of skirts will keep your style updated.

You can go for knee-length boots and tights in the cold months and opt for shorter ones once the weather gets warmer. The same applies to the type and the length of skirt that you choose to pair with your boots. This is one of the most versatile and timeless styles.

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