Should you wear the cowboy boot?
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Earlier this year, social media star turned model turned tequila entrepreneur Kendall Jenner posted two sets of personal snaps wearing cowboy boots to Instagram. In the first, she teamed them up with a long pink floral summer dress with puffed sleeves while frolicking in the spiky grass and then cradling a rooster. In the second, she wore them with nothing but a nude bikini and a new layer of baby oil. A recognized fan of Kendall (don’t judge me!), I was one of over 10 million people who immediately liked both posts. But these images marked me for months. It was the ease 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 heart of the American Midwest, a place where cowboy boots aren’t a seasonal trend but a staple of classic footwear. As a child, I thought my Uncle Fred was Clint Eastwood’s double. At our family farm, we took cart rides and sang Hank Williams songs in the summer moonlight. When I was 30, I threw a country-western themed birthday party and invited all my fashion friends over to the house with me for a hoedown. Suffice it to say, we weren’t that rural that I had to ride horses all the way to high school (I actually drove a Toyota Camry). But some days I dressed the way I could.
Denim jackets, Bud Light and cowboy boots: these were the sartorial calling cards of my people. And in her two posts, Jenner, 25 – who has more than 180 million followers on Instagram – officially welcomed one of them into a new generation. A poster girl for the Gen-Z style, her team – which includes Hailey Bieber and Bella Hadid, the girls who once brought back ’90s crop tops, miniature sunglasses and high-waisted wide-leg jeans – were going doing “shit kickers,” as we call them back home, are going viral again.
One of the first people I sent Jenner’s photos to was my friend Lauren Santo Domingo, a full-fledged style star and co-founder of online retailer Moda Operandi. I asked her if she had seen cowboy boots coming back. “Duh,” she replied. Hedi Slimane at Céline, Daniel Lee at Bottega Veneta, John Galliano at Maison Margiela: the biggest names in fashion had presented their own versions. “Cowboy boots – ‘but make them trendy,’ as kids’ memes would say,” Santo Domingo added when we reconnected on the topic more recently. “We see a lot of cowboy-inspired boots because they are a great alternative to the more traditional flat boots. They have a low heel and, without seams, they go very well with the dresses in earth tones of the season. On her site, she told me The Pasa Fino boot by Johanna Ortíz ($ 850) and the Fontana knee high boots by Khaite ($ 980).
I ask Santo Domingo if she thinks some people are better suited to shit kickers than others. “I guess it comes more naturally to some, probably in the way people on the East Coast are very used to wearing Birkenstocks,” she says. “But let’s face it, both are all the rage right now.”
The official history of the cowboy boot is as murky as a bottle of homemade moonlight, but we do know that they began to appear in the trades at the end of the 19th century. Cattle riding was a huge affair on the plains of the American Old West, and after the Civil War these men developed a simple, slip-on design with crisp sides for easy sliding in and out of a saddle, and a pointed end to aim the caliper.
According to Luke Meagher, the fashion critic behind the High fashion YouTube channel, a new generation of young designers sheds a different light on style. “Pyer Moss and Brother Vellies collaborated on cowboy boots for Kerby-Jean Raymond’s third American Also collection. It helped restore Raymond’s attention to the often-forgotten history of black cowboys in America, ”he says. Raf Simons’ Calvin Klein reinterpreted American culture with a line of cowboy boots on the catwalk, while Margiela’s deconstructed perspective explored it in a way that still felt authentic to the brand. “
Do cowboy boots go with anything? “Jeans, always, babydoll dresses, gingham, shorts and leggings,” Meagher explains. “Three-piece suits, especially when the pant legs are not tucked into the boots” are among the pieces Meagher says they don’t fit.
One place where cowboy boots have always been in fashion is my house. The first time Santo Domingo wore them in a non-ironic way was on my aforementioned 30th birthday, which I hosted with some of my best friends from high school in Missouri, 2012. Model Karlie Kloss, who grew up not far from me. , dug up the boots she wore in high school for the occasion. VogueHamish Bowles was delighted to wear a pair of soft lilac leather ropes, which he had had made in Texas years before. Sadly, the theme, “country bumpkin couture,” was a paradox for Swarovski stylist and creative director Giovanna Battaglia Engelbert, who presented herself with the Pumps inspired by Cadillac by Prada Spring / Summer 2012. It’s not uncommon for a European to mistake California oilers for country cowboys, but rest assured, she has since acquired the proper footwear for a Blasberg family hoe should the opportunity arise again. “I should have worn cowboy boots: much better for dancing,” she told me. Well it’s my 40th next year.
If you don’t take my word for cowboy boot culture, take it from a true Southern icon. “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 The clothier James in 2015. “They go with everything. David Lauren, son of Ralph Lauren, is another Southern inspired footwear expert who has done more for the 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 paired them with jeans, a suit or even a finely beaded evening dress.
A few months after Jenner’s post, I watch CNN to see Jeff Bezos complete his 10-minute mission in space. When his capsule lands in the West Texas desert, his girlfriend, Lauren Sanchez, runs into the field to see the Blue Origin crew open the hatch. She wears 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 the vast wilderness of South America, have reached the slopes of Milan and Paris. And maybe, one day, in space and beyond. Stunning, indeed.