7 Dresses That Look Amazing With the Boots Everyone's Buying

Just because the bold, must-try boots of the season have some Halloween party potential doesn’t mean that they’re strictly are a costume piece. On the contrary: Western boots are arguably they’re one of the most versatile items you can add to your closet right now—and the below seven outfits featuring cowboy boots with dresses prove it.

When it comes to styling the classic and rugged shoe trend, denim is always a solid choice. However, if you’d like to avoid any hint of rodeo references, we suggest a two-piece outfit combination recently spotted across street style photos from New York to Paris. Whether midi or maxi, structured or frilly, dresses of all sorts complement cowboy boots’ signature Americana charm, chunky heels, and (often) decorated leather exterior.

To make test-driving the look a bit easier, we’ve outlined our favorite examples to re-create now. Keep scrolling to see and shop them all.

High-Slit Dress

A generous high slit has always been appealing if you’d like to flash a thoughtful bit of leg. In this case, the cheeky silhouette is also perfect for peeking at beautifully detailed Western shoes.

Wrap Dress

Like cowboy boots, wrap dresses are a timeless silhouette. Their popularity may ebb and flow, but both always have a place in our closets—and yes, they look even better when worn together.

Trapeze Dress

The combination of oversize dress and chunkier boots feels daring and playful. We're all about it.


The beauty of a classic button-down shirtdress is its ability to be worn with nearly any pair of shoes, so swap in a pair of cowboy boots for an update to your office look.

Slip Dress

Slip dresses with cowboy boots



We’re all about an unexpected pairing, and the combination of a delicate, slinky slip dress with rugged boots is one of our current favorite contradictions.

Ruffle Dress

A touch (or a ton) of frill also brings some lightness to this tougher shoe trend.

Peasant Dress

An over-the-knee pair of Western boots makes an on-trend prairie dress feel fresh and modern.