As autumn approaches, cowboy boots instantly make another comeback. The shoe style that has smoothly transitioned from a seasonal trend to a full-on modern classic won the hearts of fashion enthusiasts with its bold yet versatile look. But what is particularly intriguing about this relatively new fashion staple is its humble, down-to-earth origin, which runs deeper than dusty Westerns. So, let’s saddle up and take a ride through cowboy boots’ history to figure out what made them timeless residents of our wardrobes.

Despite the name paying homage to North American cattle herders, cowboy boots didn’t just magically appear out of nowhere. Their story stretches back to the Spanish conquistadors, who wore sturdy leather footwear during their explorations of the Americas in the 16th century. 

These guys needed durable shoes that were suitable for rugged terrain and horseback riding. The solution was tall leather boots with high shafts to protect their legs, pointed toes for easy slipping into stirrups, and sturdy heels to help them stay steady in the saddle.

These practical shoes were later adopted by vaqueros — skilled horsemen and cattle herders who originated from the Iberian Peninsula. With Spanish expansion establishing settlements in the New World, they became prominent in Mexico and the southwestern United States, playing a crucial role in the development of ranching culture in the Americas. Over time, these boots adapted to local needs, gaining the recognisable Western look we know today. 

Still, even though the groundwork for the modern cowboy boots prototype was laid by the Spanish, the concept of riding shoes was not a localised phenomenon. Similar footwear styles aimed at horse riders existed around the world for centuries. 

You might wonder why ordinary people suddenly started wearing cowboy shoes outside of ranches. The answer is prosaically boring — pop culture. In the 20th century, Hollywood cranked out Westerns like they were on an assembly line, showcasing cowboy boots worn by the era’s icons. Brought to the big screen, they became symbols of masculinity and rugged charm. To feel like you were art and part of this adventurous lifestyle, you didn’t need to work the land anymore. Everyone wanting to add a little flair to their image could simply buy a pair of cowboy boots — even if they had never seen a horse in their life. 

As time passed, cowboy boots continued to gain traction beyond their rustic roots. Designers like Ralph Lauren started incorporating them in their collections, reimagining the signature silhouette. In no time, cowboy boots evolved from a mere fashion trend to a timeless wardrobe staple that now can be found in permanent lines of reputable labels from Isabel Marant and Chloe to Saint Laurent and Khaite.