How To Wear Cowboy Boots Without Feeling Costume-y

If you’ve been perusing the interwebs in search of a new pair of shoes, chances are you’ve spotted a surplus of western styles on the market. Over the past couple of seasons, cowboy boots have been sprinkled throughout designer collections (originating at Calvin Klein), continuing to pop up in various forms from city-sleek versions to well-worn styles at Fendi, Isabel Marant, and Givenchy, to name a few. This fall marks the peak of cowboy culture with equestrian-inspired boots officially finding their place atop the shoe charts as the biggest footwear trend of the season. Honestly and truly.

Cowboy boots might seem like a polarizing trend, and sure, they can be tricky to pull off with aplomb. Per the runways, the modern way to wear them is not in the assumed sense—meaning, don’t go running off and styling them with head-to-toe denim, a suede jacket and a Stetson hat. Yes, more literal interpretations of cowboy boots stomped across a few catwalks, but that’s not what we’re focusing on. Instead, we’re tuned into fall’s fresher take on the boot which involves them styled in juxtaposition with tailored separates and feminine staples. In other words, you want to wear cowboy boots with the pieces you wouldn’t naturally pair them with. We said it was tricky.

Rachael Wang, a stylist and brand consultant, is somewhat of a street style fixture with a proven track record for wearing cowboy boots the au courant way. “My personal favorite way to wear the trend is by combining it with another big fall and winter trend, corporate style suiting,” she explains. “To me, pairing a checked pencil skirt or simple grey pantsuit with cowboy boots is unexpected and keeps any given outfit from feeling too thematic.”

Wang’s advice is perfect for planning a fall foray into the trend, and yet, there’s no reason you can’t take cowboy boots for a spin now. In fact, designers put a big emphasis on the western style for pre-fall, including Tibi, Altuzarra and Nina Ricci. “I love the juxtaposition of showing skin on top via bare shoulders, while covering the legs by pairing a skinny strap midi-length dress with tall cowboy boots,” Wang adds. “This is a great way to wear the trend while the weather is still quite warm.” Intriguing, right?

Since cowboy boots aren’t exactly the easiest look you’ll come across this year, we’re decoding the movement by sharing three fresh outfit formulas inspired by Wang’s savvy style advice. Yes, you can pull off cowboy boots and you should. Here’s how!

Getty Images

Western Influence

With A Dress

While the weather’s still warm, take a cue from Wang and style a slinky slip dress over a sturdy pair of cowboy boots. Aim for a fluid silhouette like this one from Everlane (available in sizes 00 to 14!) with side slits that allow the midi to float over the hefty footwear style. Chain-link earrings and a beaded bag are summer-perfect accents on balmy nights.

With A Suit

Shake up your suiting with a cool pair of cowboy boots. The key to this formula is choosing a sleeker boot silhouette so the overall effect reads polished (an ankle length tucks better under trousers). A simple white tee brings an easiness to the look while a sleek white bucket bag lends a sophisticated pop.

With A Pencil Skirt

Riffing off Wang’s advice, a tall pair of cowboy boots is unexpectedly cool with a prim pencil skirt. Let this look drift in a feminine direction by pairing with a puff-sleeve blouse, unique pair of statement earrings and two-tone bag.