Should you wear the cowboy boot?

Earlier this year, the social-media star turned supermodel turned tequila entrepreneur Kendall Jenner posted two series of personal snaps wearing cowboy boots on Instagram. In the first, she teamed them with a long pink floral sundress with puffy sleeves while frolicking in spiky grass then cradling a rooster. In the second, she wore them with nothing but a nude-coloured bikini and a fresh coat of baby oil. An admitted Kendall fan (don’t judge me!), I was one of the more than 10m people who liked both posts immediately. But these images stuck with me for months. It was the easy-breezy effortlessness with which she wore the boots, and the decadence of pairing them with a string bikini. It made me feel… a sense of pride?

I grew up in Missouri, the heartland of America’s Midwest, a place where cowboy boots are not a seasonal trend but a classic footwear staple. As a kid, I thought my uncle Fred was Clint Eastwood’s stunt double. At our family farm, we went on hayrides and sang Hank Williams songs in the summer moonlight. When I turned 30, I threw a country-western themed birthday and invited all my fashion friends to come home with me for a hoedown. Suffice to say, we weren’t so rural that I had to ride a horse to high school (I drove a Toyota Camry, actually). But on some days I dressed like I could have.

Denim jackets, Bud Light and cowboy boots: these were the sartorial calling cards of my people. And in her two posts, 25-year-old Jenner – who counts more than 180m Instagram followers – was officially welcoming one of them to a new generation. A poster girl for Gen-Z style, her crew – which includes Hailey Bieber and Bella Hadid, the girls who already brought back ’90s crop tops, miniature sunglasses and high-waisted wide-leg denim – were going to make “shit kickers”, which is what we call them back home, go viral once again. 

Cowboy boots do not go with three-piece suits, “especially when the pant legs are poorly tucked into the boots” 

One of the first people I messaged Jenner’s pictures to was my friend Lauren Santo Domingo, a style star in her own right and co-founder of online retailer Moda Operandi. I asked if she had seen cowboy boots coming back. “Duh,” she responded. Hedi Slimane at Celine, Daniel Lee at Bottega Veneta, John Galliano at Maison Margiela: the biggest names in fashion had introduced their own versions. “Cowboy boots – ‘but make it fashion’, as the kids’ memes would say,” Santo Domingo added when we reconnected on the topic more recently. “We are seeing a lot of cowboy-inspired boots because they are a great alternative to the more traditional flat boot. They have a slight heel, and without stitching they go great with the season’s earth-toned dresses.” On her site, she pointed me to Johanna Ortíz’s Pasa Fino boot ($850) and the Fontana knee-high boot by Khaite ($980).

I ask Santo Domingo if she thinks some people are better suited to shit kickers than others. “I guess it does come more naturally for some, probably in the way people from the East Coast are very accustomed to wearing Birkenstocks,” she says. “But let’s face it, both are in fashion right now.”

The official history of the cowboy boot is as murky as a bottle of homemade moonshine, but we know they began to show up in the trades in the late 19th century. Cattle driving was huge business in the plains of America’s Wild West and, following the Civil War, these men developed a simple, laceless design with clean sides to easily slide on and off a saddle, and a pointed toe to aim for the stirrup.

According to Luke Meagher, the fashion critic behind the Haute Le Mode YouTube channel, a new crop of young designers is shining a different light on the style. “Pyer Moss and Brother Vellies collaborated on cowboy boots for the third American Also collection by Kerby-Jean Raymond. It helped re-establish Raymond’s calling attention to the often-forgotten history of black cowboys in America,” he says. “Raf Simons’s Calvin Klein reinterpreted American culture with an array of cowboy boots on the runway, while Margiela’s deconstructed take explored it in a way that still felt authentic to the brand.”

Do cowboy boots “go” with anything? “Jeans, always, babydoll dresses, gingham, booty shorts, and chaps,” says Meagher. “Three-piece suits, especially when the pant legs are poorly tucked into the boots” are among the pieces with which Meagher says they do not go. 

One place cowboy boots have always been in fashion is my house. The first time Santo Domingo ever wore them in a non-ironic way was to my aforementioned 30th birthday, which I organised with some of my best girlfriends from high school in Missouri, 2012. The model Karlie Kloss, who grew up not far from me, dug out the boots she wore in high school for the occasion. Vogue’s Hamish Bowles was thrilled to wear a pair of supple leather lilac ropers, which he had had made in Texas years before. Sadly, the theme, “country bumpkin couture”, was a paradox for stylist and Swarovski creative director Giovanna Battaglia Engelbert, who showed up wearing the Cadillac-inspired heels by Prada s/s ’12. It’s not uncommon for a European to confuse California greasers with country cowboys, but rest assured she has since acquired the appropriate footwear for a Blasberg family hoedown should the occasion arise again. “I should have worn cowboy boots: much better for dancing,” she tells me. Well, it is my 40th next year. 

If you don’t take my word on cowboy-boot culture, take it from a bona fide Southern icon. “Down here in the South, a cowboy boot goes with a dress, goes with jeans, goes with shorts,” says Reese Witherspoon, who grew up in Tennessee and founded a Southern-inspired fashion brand called Draper James in 2015. “They go with everything.” Another expert on Southern-inspired footwear is David Lauren, son of Ralph Lauren, who has done more for cowboy style than anyone since John Wayne. “Cowboy boots have always been an icon of rugged individualism and American style.” He also argues that they go with everything: “We’ve paired them with jeans, a suit or even a finely beaded evening gown.” 

A few months after Jenner’s post, I am watching CNN to see Jeff Bezos complete his 10-minute mission to space. When his pod lands in the West Texan desert, his girlfriend, Lauren Sanchez, runs out to the field to see the Blue Origin crew open the hatch. She is wearing a white Oscar de la Renta dress, a cowboy hat, and – you guessed it – cowboy boots. I feel that sense of pride again. These shit kickers, with their origins in the plains of America’s vast Southern wilderness, have made it to the runways of Milan and Paris. And maybe, one day, to space and beyond. Giddy up, indeed.