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Horses to Hollywood to High Fashion: The History of the Cowboy Boot


Image via iCollector

The cowboy boot is a peculiar shoe. Like America’s political sphere, it has been rent down the middle and split to the far ends of the spectrum. These Cuban-heeled beauties can be found either crushing empty tall-boys in middle America or clomping up and down runways in Paris and New York. But where’s the middle ground? It’s a divisive boot that’s seen stirrups, the silver screen, sidewalks and catwalks, and we’re walking through it all.


Duke of Wellington in the boots that would gain his name – note the insane moose-knuckle. Image via Cowboy Boots Hub.

Before the Cowboy Boot

It’s hard, nigh impossible to trace the exact history of a garment that has been produced by countless manufacturers since the 1800s, but the online consensus seems to be that the Wellington Boot is the closest relative to the modern cowboy boot. Now associated with rubberized, waterproof rainboots, the original Wellingtons were a British cavalry riding boot, first made-to-order for Arthur Wellesley, the Duke of Wellington. These were essentially a pared down version of the earlier Hessian Boot, which had been the de facto military riding boot for aristocratic military types. The Wellington boot was a softer, closer-fitting boot that stripped away many of the frills and tassels associated with aristocratic combat boots. Unwittingly, the Duke began a major trend with his boots, which were markedly easier to produce than any preceding style. Not only did other fashionable upper-crust types adopt this style (Beau Brummell, for one), but they found themselves on the feet of countless foot soldiers in the years to come.


Union Soldier. Image via The Golden Assay.

Wellington boots came to the United States in a big way when the Civil War began. This huge military conflict at the very dawn of industrialization was one of the first times in human history that troops were really properly suited up in matching uniforms. In fact, our modern sizing method (S, M, L, etc.) was invented during the Civil War to help soldiers find their correct fit in tons of mass-produced garments. The Wellington boot, with no laces, buckles, or any sort of frills was a great option for troops, as they could be produced en masse and held up well to the stresses of modern warfare.

The Cowboy Gets Its Heel


Couple Cowgirls. Image via True West Magazine.

The distinguishing feature of the cowboy boot is its distinctive heel. That canted, high-ish heel is known in the footwear world as a “Cuban Heel,” the likes of which we admired in our article on true Chelsea Boots. The great thing about this heel, besides its obvious aesthetic benefits, was that it gave riders greater leverage in the stirrups when they rode. As one-time soldiers demobilized and made their ways westward to find their fortunes, they adopted these boots, which married the best of the Wellington tradition, with the Cuban-soled goodness of the Vaquero Culture, a style of riding that began in Spain, but moved to Latin America as the Spanish pillaged the treasures of Mesoamerica.

The rounded toe of the original Wellington boot wound up slightly pointed or squared off in cowboy boots, which pinched the riders’ toes, but made it easier for these caballeros to guide their feet into the stirrups in a hurry. The light calf-skin that Wellesley used in his original boots back in England was swapped out for hard-wearing steerhide and the boots stayed relatively high so that cowboys could protect their feet and calves from tough scrub and brush on the trail.

Cowboy Boots Get Fancy


Tom Mix. Image via Fox.

With Cowboy boots, it’s often hard to discern if they’re art imitating life, or the other way around. Many cowboy boot aficionados feel that the most exaggerated styles of cowboy boots are really just imitating those worn in early Westerns, like these stunners worn by silent-era star Tom Mix, pictured above. Whether or not the choice to incorporate increasingly exotic designs and materials was a natural one, or simply to imitate the increasingly omnipresent faux-Western styles, cowboy boots grew increasingly garish. These boots had always been stitched on the outside to prevent the leather from buckling or from rubbing on the wearers’ legs, but this distinct style of construction was conducive to decorating the boots with zany patterns.


Lucchese Boots. Image via Houston Chronicle.

Thought it’s pretty much impossible to figure out who made the first ever cowboy boot, we know for a fact that Lucchese was one of the brands to bring cowboy boots into the limelight. We covered this famous brand a while back, but the gist is that these Italian immigrants brought their old-world cobbling know-how to the nascent world of cowboy boots in the late 1800s and even incorporated new technologies that made mass-production easier. Their boots exist in the uncanny valley between the functional minimalist boots worn by the first generation of cowboys and the stylized Hollywood-ified versions that came around the time that the Wild West started to be romanticized onscreen. Their stuff is tough, and most people agree, the real deal and they are one of the few companies to have consistently produced cowboy boots since around the time of their inception.

The Cowboy Boot’s Close Cousins


Pecos Boots in the stockyards. Image via Red Wing

As actual cowboys started to vanish and fictional cowboys started to dominate the collective consciousness, their footwear grew increasingly impractical and expensive. For every Hollywood star getting made-to-order alligator skin boots, there were thousands of average joes who needed something to protect their feet on the job. The cowboy boot was growing distant from its working class roots; more for film-set peacocking than for wrangling. It was in this atmosphere that new, humbler versions of the cowboy boot were introduced. Red Wing launched their Pecos Boot in the 1950s, to introduce an aggressively toned-down boot that mimicked the silhouette of the iconic boots that won the West, but with a little less extraneous detailing.


Paul Newman in short-shafted Roper Boots. Image via Pinterest.

Roper Boots also grew popular, first among actual riders, mostly in the rodeo scene, and then with the general public. The most important identifier of a roper boot is the lowered heel. Designed for riders who were roping calves, they needed to accommodate these guys hopping off their horses and running to wrestle the calves to the ground. The two-inch heel of the original cowboy boots might have offered great arch support, but they didn’t make for great running shoes. Therefore, the roper boot’s heel was lowered to a mere half inch, and because these riders weren’t out in the scrub, mostly just in the rodeo ring, the shaft could be lowered too. Lower heels and lower shafts made these boots a smash hit with the general public. They weren’t as fitted as your average cowboy boot and their styling was markedly pared down. Even the most self-conscious guy wouldn’t feel weird slipping them on.

Moving Forward


A little more Newman. Also Redford. Image via Pinterest.

The most important and enduring thing about the cowboy boot is its unique silhouette. Its high shaft and high heel make for an elegant, fitted look, especially as you break them down and they start to adhere to your feet and calves. The things that make cowboy boots the least approachable, namely the crazy swirly stitching and garish colors and materials aren’t a necessary part of the equation. The over-stylized elements of the cowboy boot, though they are an important part of the history, are mostly the work of Hollywood costume departments. This caused a trend that rippled outward and onto the feet of actual cowboys, blurring the line between authenticity and fiction.


Ted Mosby’s red boots. Image via E News.

Though both ends of the spectrum tend to embrace the cowboy boot’s more garish elements, the rest of us can keep a more even heel. For a boot that makes you feel good, functions as it should, (fits under your jeans, please don’t wear them outside of your jeans) and blends in with your urban lifestyle, investigate those humbler relatives of the cowboy boot—or dig deeper into the reference material. You’ll definitely be able to find something in a tasteful suede or plain steer hide that gives you the cowboy edge you’ve always wanted without making you a laughing stock.

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