How to Wear Ankle Boots With Skirts

Ankle boots are one of the most versatile and timeless pieces in any woman’s wardrobe. While they originally made their mark as a practical shoe style for cooler days, ankle boots have evolved into a true fashion statement. Their ability to class up virtually any outfit, from casual jeans to semi-formal skirts, is why so many of us can’t resist adding yet another boot option to our collection each season.

How to Wear Ankle Boots With Skirts

In this post, I’ll be sharing some of my favorite ways on how to wear ankle boots with skirts for a look that is perfectly put together whether you’re heading to the office or out for after-work drinks with friends. From casual A-line mini skirts to figure-hugging pencil styles, ankle boots allow you to take your skirt from day to night while keeping both comfortable and on-trend. Let’s get started!

9 Best Ways on How to Wear Ankle Boots With Skirts

1. Tuck in a Flowy Midi Skirt:

One effortless way to pull off ankle boots with skirts is by tucking in a flowy midi skirt. This look creates a fashionable and flattering silhouette, highlighting your waistline while also elongating your legs. Pair this combo with a fitted top and accessorize with statement jewelry for an elevated daytime look. This style works especially well with pointed-toe ankle boots for a chic and sophisticated touch.

Tucking in a Flowy 
Midi Skirt

2. Try the Ankle Bootie Sock:

The ankle bootie sock is a popular trend among fashionistas and has quickly become a staple in many wardrobes. This style of boot features a higher shaft that sits just above your ankles, creating the illusion of elongated legs. This makes them an excellent choice to pair with skirts, as they add a touch of elegance and elongation to any look.

3. Add Some Edge with Leather Skirts:

For a bolder and edgier look, try pairing your ankle boots with a leather skirt. This combination creates the perfect balance between feminine and edgy, making it ideal for a night out on the town. You can opt for a sleek pencil skirt or a flared A-line style, depending on your personal preference and the occasion. Adding a leather jacket and statement accessories will complete this chic look.

4. Go for a Monochromatic Look:

One way to keep your outfit looking cohesive and put together is by opting for a monochromatic look with your skirt and ankle boots. This means choosing pieces in the same color family, such as black or brown, to create an effortlessly chic ensemble. You can also add layers, like a cardigan or blazer, to add depth and texture to your outfit.

Opting for a Monochromatic Look

5. Mix Textures and Prints:

Another way to add interest to your skirt and ankle boot combination is by mixing textures and prints. This can be achieved by pairing a flowy floral skirt with a chunky knit sweater and suede ankle boots. Experiment with different patterns and textures to find a combination that speaks to your style. Mixing textures and prints can add a fun and playful element to your outfit.

6. Try Different Boot Heights:

While the classic ankle boot sits just above your ankle, there are also other boot heights that you can experiment with. For example, try pairing a midi skirt with knee-high boots for a more dramatic look, or opt for calf-length boots to pair with a mini skirt. Playing with different boot heights can add variety and interest to your outfit.

7. Layer with Tights:

Ankle boots are a great option for cooler weather, but you may find yourself wanting some extra warmth on particularly chilly days. This is where tights come in handy! Layering tights under your skirt and ankle boots not only adds warmth but also creates a stylish and polished look. You can choose from opaque tights for a sleek appearance or go for a patterned pair to add some interest to your outfit.

8. Dress Up with a Maxi Skirt:

Who says you can’t wear ankle boots with maxi skirts? This combination is perfect for fall and winter days when you want to keep your legs covered but still look chic and put together. Pair a flowy maxi skirt with ankle boots, tuck in a fitted top, and add a belt to cinch in your waist for a bohemian-inspired look.

9. Go Casual with Denim:

Lastly, you can never go wrong with the classic combination of denim and ankle boots. This pairing is perfect for a casual day out or running errands, as it is comfortable yet still stylish. Try pairing your favorite denim skirt with ankle boots and a cozy sweater for a look that is effortlessly cool and chic. This is also a great option for transitioning your summer skirts into fall and winter.

 Pairing Your Favorite Denim Skirt With Ankle Boots

There you have it – nine different ways to wear ankle boots with skirts! From dressing up in leather skirts to keeping things casual with denim, there are endless options for creating stylish and versatile looks with this classic shoe style. So why not dust off your favorite ankle boots and start experimenting with different skirt combinations? You’ll be sure to find a look that suits your style perfectly.  Happy styling!

Additional Tips and Tricks to Wear Ankle Boots With Skirts

1. If you’re feeling bold, try pairing a brightly colored or patterned skirt with neutral ankle boots. This will add a pop of color to your outfit and create a fun, unexpected look.

2. Play with proportions by wearing a mini skirt with knee-high or over-the-knee boots. This can help elongate your legs and give the illusion of height.

3. If you’re worried about your skirt looking too short with ankle boots, try layering a longer cardigan or jacket over it. This will add some coverage and balance out the length.

4. For a casual and comfortable look, pair ankle boots with a flowy midi skirt. This combination is perfect for running errands or grabbing coffee with friends.

5. Don’t be afraid to mix textures. Try pairing a leather skirt with suede ankle boots or a denim skirt with velvet ankle boots for a unique and stylish outfit.

6. To transition your ankle boots into the colder months, add tights or leggings underneath your skirt. This will keep you warm and allow you to continue wearing your favorite skirts all year round.

7. For a sleek and sophisticated look, wear a pencil skirt with pointed-toe ankle boots. This combination is perfect for the office or a dressy event.

8. When in doubt, opt for black ankle boots. They are versatile and can be worn with almost any color or style of skirt.

9. Experiment with different heel heights to change up your look. Ankle boots come in a variety of heel heights, from flat to high heels, so don’t be afraid to try different options.

Experiment With Different Heel Heights

Following these tips and tricks will help you create stylish and unique outfits with ankle boots and skirts. Remember to have fun and mix and match different pieces to find your perfect look!  So, don’t be afraid to step out of your comfort zone and try new combinations. With the right styling, ankle boots can elevate any skirt outfit and take it to the next level. Happy experimenting! 

Frequently Asked Questions

Do Ankle Boots Go Well With All Types of Skirts?

Yes, ankle boots can be paired with almost any type of skirt. From flowy maxi skirts to form-fitting pencil skirts, ankle boots add a touch of edge and sophistication to any look. However, it’s important to consider the length and shape of your skirt when choosing the right pair of ankle boots.

What Length of Skirt Should I Wear With Ankle Boots?

The length of your skirt is a key factor in creating a flattering outfit when wearing ankle boots. As a general rule, skirts that hit just above or below the knee tend to look best with ankle boots. This allows for enough leg coverage while also showcasing the boots.

How Do I Choose the Right Ankle Boots for My Skirt?

When choosing an ankle boot to pair with your skirt, consider the color and style of both pieces. For a cohesive look, opt for ankle boots in a similar or complementary color to your skirt. If your skirt is patterned or bold, stick to neutral-colored ankle boots to balance out the outfit.

Can I Wear Ankle Boots With Tights?

Yes, you can wear ankle boots with tights. This is a great way to transition your ankle boots into the colder months. When pairing tights with ankle boots, consider the color and material of both pieces. Black tights tend to pair well with any colored boot, while colored or patterned tights can add a fun pop of contrast.

Are There Any Skirt Styles That Don’t Pair Well With Ankle Boots?

While ankle boots can generally be worn with any skirt style, there are a few exceptions. Avoid pairing ankle boots with midi or maxi skirts that hit at the widest part of your calf, as this can create an unflattering silhouette. It’s also best to avoid wearing ankle boots with very short skirts, as this can make your legs look disproportionate.


Knowing how to wear ankle boots with skirts can elevate your style and add versatility to your wardrobe. Keep these tips in mind when pairing ankle boots with skirts to create chic and effortless outfits. Remember, the most important thing is to choose a skirt and boot combination that makes you feel confident and comfortable. Experiment with different lengths, styles, and colors to find what works best for you.  So go ahead and rock those ankle boots with your favorite skirts!  Happy styling.  

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Jennifer Branett

I am Jennifer, a passionate blogger since 2016. I like to write informative articles to help peoples in my free time. I am a family person. I have two kids who keep me busy all the time. I always try to give importance to my family. Sometimes it becomes challenging for me to maintain the time along with my family. But I never lose hope. I hope my articles are helping you in some way. If so, You can give me a thumbs up to my inbox, which means a lot to me. Thank you. You can email me at

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