21 Cute Skirts to Wear With Cowboy Boots

Everyone wants to be fashionable but to do that, you need to know what best flatters your accessories and body shape. Some pieces, such as the American classic cowboy boots, can be hard to match with your outfit. However, practice makes perfect. 

If you, like many others, wonder what to pair with your cowboy boots, keep reading as we are here to give you a crash course on cute skirts to wear with cowboy boots. We will share ideas on how to pair cowboy boots with different skirts for style, elegance, and comfort. From denim skirts to floral skirts, there's something for everyone in this roundup. 

So don't wait – get inspired and start shopping for your next outfit.

1. Blue Floral Pleated and Slit Skirt and Knee-Length Cowboy Boots

Are you headed for that Sunday brunch or Easter dinner? You'll be sure to impress in this fun, casual outfit that combines a pleated skirt and matching top. The choice of colors and design can give you a unique look that will help you make an entrance.

2. A Flirty White Tulle Skirt With Light Brown Cowboy Boots and A Jean Jacket

This is a perfect look for a date night or girls' night out. You'll feel beautiful and feminine in this outfit. With a lovely tulle skirt, you have countless options of what top to wear, such as a denim shirt or white top.

3. Cute Black Velvet Skirt With Snakeskin Cowboy Boots

Going to an intimate dinner or holiday party? Then look no further than this amazing outfit. You'll be sure to feel chic and elegant with this look. Not only does the black velvet skirt look luxurious, but the printed boots also up the game.

4. Flirty Pink Mini Skirt Paired With A Graphic T-Shirt and White Cowboy Boots

Flawless for a first date or going out dancing, this fashion choice will make you feel sexy. The matching boots and top blend perfectly, making this look ideal for many events and occasions.

5. Casual and Relaxed Black Chambray Denim Skirt With Flared Pockets and Dark Brown Cowboy Boots

When you're running errands or going to class, you need something that offers support for your feet and guarantees comfort. And what better way to ensure you’ll feel comfortable on busy days than this casual look? Give it a try, and you won’t regret it.

6. Flowery Maxi Skirt Paired With a White Tank Top and Flowered Cowboy Boots

This is a perfect look for a lunch date or dinner with friends. You'll feel confident and stylish in this outfit. The prints make it look more sophisticated. You can always add a touch of class to your look with accessories such as a cute purse or belt.

7. Shiny Brown Cowboy Boots With A Faded Jean Skirt and Casual Sports T-Shirt

This is a perfect look for a day out shopping or running errands. When you pull this look, you'll be sure to get compliments all day. A denim mini-skirt can help spice up this look. But it doesn't have to be short. Just go with your preference and be confident.

8. Dazzling Green Sequined Skirt and Knee-Length Cowboy Boots

This is a perfect look for New Year's Eve or a holiday party. You'll be sure to dazzle in this cute outfit. You can't go wrong with a pair of cowboy boots and a sequined skirt. However, ensure the colors blend for that polished look.

9. Floral Pencil Skirt and Blue Chambray Shirt Paired with Cowboy Boots

Wondering what to wear for that job interview or an important meeting? Try combining a pencil skirt and cowboy boots. This outfit conveys class and a fashion sense, so you'll be sure to turn heads. Depending on the color of the boots, you can use a flattering color to add to the look.

10. Ankle-Length Cowboy Boots and a Flowery Off-Shoulder Top

This is a perfect look if you want to impress. You'll feel confident and sexy in this cute outfit. The short wrap skirt, designed to look more like a short, blends very well with her style and accentuates her features.

11. Cute and Bold Pleated Floral-Print Skirt and Black Cowboy Boots

Are you looking to make a statement? You'll be sure to stand out in a printed skirt and cowboy boots. Finishing the look with something like a denim jacket will also add to your appeal.

12. Pretty White Lace Skirt and Butterfly-Print Cowboy Boots

This is a perfect look for Valentine's Day or an anniversary dinner. You'll feel beautiful and feminine in this outfit, as the lace adds a layer of sophistication.

13. High-Waisted Knee-Length Skirt and Brown Cowboy Boots

This is a perfect look for a costume party or Halloween. You'll feel like you stepped out of a time machine in this fashionable outfit.

14. A Sophisticated Leather Print Midi Skirt, Mid-Shin Brown Cowboy Boots, and Printed T-Shirt Combo

Ideal for an event or dinner party, this look communicates a fun yet casual vibe. You'll be sure to impress in this outfit while looking great.

15. A Classic Short Black Leather Skirt Combined With Cowboy Boots

This is the ultimate look for a night out on the town that'll be sure to turn heads. A short leather skirt looks especially striking when you match the color of the boots and use a neutral color such as a white top to blend perfectly.

16. Preppy Matching Black Plaid Skirt and Jacket Paired With Black Cowboy Boots

The perfect look for running errands or going to class, a plaid skirt and cowboy boots help combine style and comfort, with a crop top and a denim jacket crowning the look.

17. Blue Knee-Length Medium Wash Skirt With Cowboy Boots

The denim look is best for casual Saturdays or events. Depending on the occasion, you can dress it up or down and accessorize it with a hat or necklace.

18. A Chic Flowered Ankle-Length Skirt With White Cowboy Boots

Every girl ponders over the best outfit to stand out in the crowd. The ankle-length skirt will help you look stylish and well put together. However, the prints on the skirt will give you the edge you need to stand out in the crowd.

19. Black and White Stylish Plaid Houndstooth Skirt and Cute Black Ankle-Length Cowboy Boots

This is a perfect look for running errands or going to class. You'll feel that you’re rocking a polished and stylish look in this outfit. Matching the colors shows you have an eye for fashion.

20. Cute Pleated Yellow-Patterned Top and Medium-Length Cowboy Boots

A perfect look for a barbecue or a day at the beach, this ensemble will have you ready to explore the great outdoors. You'll feel comfortable and stylish in this outfit. Ensure you choose the colors wisely.

21. Cute Black Striped Skirt With Orange Top and Brown Cowboy Boots

This is a perfect look for a summertime picnic or trip to the shore. You'll feel like you're on vacation in this fun and colorful outfit.

Summary and Top Picks

There's just something about cowgirls that capture our hearts. Maybe it's the way they can ride a horse and look good doing it. Or, perhaps it's their independent spirit and fun-loving nature. 

Whatever you choose, your friends won't help but admire your sense of style. However, although it is difficult to choose the perfect outfit for a specific occasion, these were my personal favorites: 

• #6 Flowery Maxi Skirt Paired With a White Tank Top, and Flowered Cowboy Boots: You can’t go wrong with this look whether you’re going for lunch or a casual night out.
• #11 Cute and Bold Pleated Floral-Print Skirt and Black Cowboy Boots: If you want to rock that spring vibe, this outfit will definitely do that for you.
• #17 Blue Knee-Length Medium Wash Skirt With Cowboy Boots: If it’s casual Friday at the office, a denim skirt is a great idea. You can give this look a little edge with ankle-length boots.