PRINCESS POLLY APP

Access exclusive deals

Rewards
Wishlist Bag 0
Home Fashion: Trending What To Wear With Cowgirl Boots

Outfits To Wear With Cowgirl Boots

The best styles to wear with cowgirl boots this year are bold, elevated, and effortlessly versatile.

Think satin mini dresses, strapless maxi silhouettes, frilly skirts, and faux leather shorts; pieces that bring just as much personality as your boots. Anything that matches the fun, cool girl energy of your cowgirl boots is a yes.

These boots are more than just a trend, they’re a statement. With their standout shape, western-inspired stitching, earthy tones, and their unmissable aura, they instantly elevate any outfit.

Whether you're heading to a festival, a night out, or just want to add extra vibes to your everyday ‘fit, keep reading to discover the outfits to wear with cowgirl boots in 2025.

woman wearing cowgirl boots 2025

Therapy Clayton Boots Maroon

woman wearing tan cowgirl boots 2025

Billini Urson Boot Tan

woman wearing black cowgirl boots 2025

Riley Boots Black

woman wearing white cowgirl boots 2025

Therapy Clayton White Boots

SHOP COWGIRL BOOTS >

Dresses To Wear With Cowgirl Boots

Enter your cute cowgirl era and pair your boots with a dress that does it all.

Our Global Style Director, Char, recommends starting with minis, especially styles in lace or satin for that vintage-inspired vibe. Patterned mini dresses are also a big yes. Think florals, leopard print, gingham, or fruit patterns to bring playful vibes to your cowgirl OOTD.

For cooler weather, maxi and midi dresses with a side split are your go-to — especially for fall or winter outfits with cowgirl boots. You’ll get that elevated floor-length ‘fit, while still letting your boots peek through and get the attention they deserve.

Tops To Wear With Cowgirl Boots

Cute tops and cowgirl boots? Say less.

When you’re looking for tops to wear with cowgirl boots, try to imagine the event or location you’ll be wearing the ‘fit to. This will guide the overall aesthetic of your look. What you wear to a concert will be totally different to what you wear to a bday brunch!

For major western energy (especially during festival szn), style your boots with a halter top in faux suede or faux leather.

If you’re putting together a look for your next girls’ night out, opt for a top with studded detailing and a flattering neckline.

Want something more low-key? A basic white tee or tank styled with mini shorts or a skirt is the elevated look you can put together in seconds.

The good news is, whatever you wear, your cowgirl boots will never fail to bring everything together.

Skirts With Cowgirl Boots

Wearing a skirt with cowgirl boots is the perfect way to balance the rugged edge of your boots with a softer, more feminine vibe.

Start with a flowing maxi skirt — the texture, volume, and movement make it the perfect match for your boots.

For something more low-key but still chic, try a midi skirt paired with a basic top for that effortlessly cool, everyday ‘fit.

Lace and ruched details are the perfect style to compliment your boots, especially when styled with a low-waisted chunky belt and a simple tank. It’s giving cool girl meets western.

Shorts With Cowgirl Boots

Shorts are the easiest, most versatile bottoms you can style with cowgirl boots.

Right now, we’re loving faux leather shorts for your party girl moments, lace shorts for something a little more playful, and ruffled skorts for peak festival/concert energy.

Micro styles never fail to bring the vibes, especially when paired with cowgirl boots and a classic fitted tank.

If you’re building an iconic party wardrobe, these are the pieces to keep on repeat. Low-rise shorts, cowgirl boots, and an elevated top? It’s a fool-proof combo.

Rompers With Cowgirl Boots

Rompers and cowgirl boots go perfectly together, especially when the romper has unique fabrics or standout details. Think slouchy, oversized fits for a boho-chic vibe, or dreamy details like ruffles, lace, or embroidery.

For something more elevated, a black romper styled with an oversized bomber jacket is the look you need for your weekend GNO plans. Whether you’re dressing it up for an event or keeping it casual, this ready-in-seconds outfit makes it easy to style around your boots.

Just add accessories and you're good to go. Zero effort, max vibes.

No matter your vibe, whether it's romantic, edgy, minimal or bold, there's a way to make cowgirl boots your own.

From cute dresses with cowgirl boots to laid-back looks with rompers, skirts or faux leather shorts, the styling options are endless.

Want more tips on how to wear cowgirl boots with a dress, a pair of shorts or a cute skirt? Find loads of outfit guides over on our TikTok @princesspolly and IG @princesspollyboutique.

Whether you're putting together casual outfits with cowgirl boots or experimenting with new silhouettes, styling cowgirl boots in 2025 is all about mixing personal style with western flair.

We can’t wait to see how you wear them!

Discover more:

OSZAR »