What to Wear with Cowboy Boots
Content editor
Else Hutt
How to style cowboy boots
Championed throughout the decades by style icons such as Princess Diana, Alexa Chung and Dolly Parton, cowboy boots have proven to have staying power. But for some, they can feel a bit like fancy dress, so how do you seamlessly integrate them into your everyday wardrobe? Start by picking the right pair for you.
If it’s your first foray into a western-style aesthetic, pick a neutral style that you can easily swap your usual footwear for. Our black leather boots are shaped with a classic point toe and Cuban heel, then adorned with silver hardware — perfect for adding a bit of edge to any outfit. Or, for a more subtle nod to the traditional style, this chunky black pair from Clarks have a simple silhouette adorned with a buckled belt.
For the braver amongst us, metallic cowboy boots are always guaranteed to make a statement. Sosandar's gold ankle boots are made in shiny crocodile-effect leather with a panelled vamp and contrasting heel. Alternatively, White Stuff's pewter boots have a more modest, smooth form yet still promise to bring shine to smart-casual edits.

The best dresses and skirts to wear with cowboy boots
Cowboy boots can be worn with pretty much any style of dress, from mini and midi to maxi dresses. Shorter styles are ideal for days spent soaking in the sun – think festivals or summer concerts – and feel particularly chic with a flared hem. This Nobody’s Child tea dress is a great choice with floral embroidery at the neck and puffed sleeves.
When choosing a longer dress to wear with cowboy boots, lean into the prairie aesthetic. This Baukjen smock dress is perfect: with a buttoned bodice and a sweeping, tiered hem it feels smart, yet laid-back.
The same rules apply when choosing a skirt. Opt for either a midi or a maxi, and remember nothing quite nails the western vibe like denim. We love our panelled maxi, that comes in a classic washed blue with a fitted waist and floaty hem.
When heading to fancier affairs, you can’t go wrong with a delicate lace skirt. The feminine vibe will perfectly juxtapose the structured, sharp form of your boots.

How to wear cowboy boots with jeans
If you’re planning on styling your cowboy boots over your jeans, opt for a skinny or slim-fit style that will avoid any bunching or billowing. For outfit inspiration, look to Princess Diana who paired hers with indigo blue jeans, a classic T-shirt and an oversized jacket.
However, if you’re simply replacing your usual boots with a western pair, opt for bootcut or flared denim that cover the ankle and show off the toe of your boot. Add a flouncy blouse and a chunky suede belt for a truly western aesthetic.
For an effortlessly chic look, try pairing yours with slouchy wide-leg jeans and a relaxed T-shirt. Complete your look with a leather jacket and a patterned neckerchief.
Published 7.21.2025
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