Can I Wear Cowboy Boots Without Looking Like I’m in Costume?

In 2023, can one wear cowboy boots in an urban setting without looking as if one has escaped a Ralph Lauren advert or a costume shop? And if so, how? — Andrea, Washington, D.C.

Few accessories are so immediately replete with mythology as the cowboy boot. A product of the great American cattle drives of the late 19th century rather than any single visionary (though Charles Hyer, a Kansas shoemaker, gets a certain amount of credit), the boot took shape as cowboys asked cobblers for modifications to the Spanish vaquero boot and the standard army boot: higher heels, to stay more anchored in the stirrup; pointier toes to slide in more easily; and scalloped tops to make pulling the boots on easier. Voilà! The cowboy boot.

The boots made their way into the popular imagination through Hollywood versions of the Wild, Wild West and came to symbolize manliness, freedom and self-sufficiency — the sense of endless horizons open to explore that was the promise of the frontier.

They became the uniforms of Texan ranchers, country-western singers and Coachella attendees, worn by the likes of President George W. Bush, Taylor Swift, Lil Nas X and, as you say, Ralph Lauren, who wears his boots with black tie and who built his empire and identity on the foundations of the American dream in all its permutations. Plenty of people still wear cowboy boots because of their functionality, but the boots long ago transcended their practical application to become totems of the nation.

All of which means that when you pull on a pair of cowboy boots, you pull on all of this potential semiology with them. They have so wormed their way into our collective hive mind that it is impossible to see a pair of boots and not immediately leap to all sorts of conclusions about the person who is wearing them. You can take the cowboy boot out of the country, but you can’t take the country out of the cowboy boot.

Yet cowboy boots are sturdy, comfortable, long-wearing and otherwise extremely useful — in many different contexts. They are a positive addition to any wardrobe and a worthwhile investment, if you can handle the hype that comes with them. So how best to do that?

I asked Angela Koh, the fashion market editor for T Magazine, who has her own pair of cowboy boots, what she would advise.

“It’s about pairing them with what you wouldn’t expect,” she said. “If you’re deciding on a pair of loafers or sneakers to go with an outfit, try swapping them out for a pair of cowboy boots. I recently tried this trick and ended up wearing my boots with my oversize wool trousers and vintage T-shirt. The subtle hint of the boots gave it a little flair.”

By subverting expectations of what goes with what, you subvert the preconceptions. Avoid fringed suede jackets and flannel shirts, for example, which have a Pavlovian connection to cowboys (and are part of the Disney cowboy costume). Instead, try a wrap dress or a banker-stripe shirt.

If you are wearing jeans, don’t wear a jeans jacket. Take a cue from Princess Diana, who famously wore her cowboy boots with blazers. A shorter dress rather than a long prairie skirt will keep them from seeming too Laura Ingalls Wilder. Cutoffs give Daisy Duke, so try culottes instead.

Whatever you do, be sure to avoid adding that other accessory: the cowboy hat — at least if you aren’t on a ranch. Halloween is still weeks away.

Your Style Questions, Answered

Every week on Open Thread, Vanessa will answer a reader’s fashion-related question, which you can send to her anytime via email or Twitter. Questions are edited and condensed.

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