The origins of the cowboy boot are as tough to pin down as, well, a wandering cowboy. The biggest myth about this most iconic form of Western footwear concerns the boot’s pointed toe. To hear some old cowboys tell it, the pointed toe was the brainstorm of a clever cowpoke with a bad sense of aim. A pointy toe, he reckoned, would make it easier for him to slip his foot into his saddle’s stirrup.

Wrong. In fact, cowboy boots had round or square toes until sometime in the 1940s, when pointy toes were introduced for reasons having to do with fashion. Other aspects of cowboy boots are more venerable. The boot’s arched sole and pronounced heel was designed to keep a rider’s foot more securely in a stirrup, and the boot’s tall shaft protected a rider’s legs from sharp brambles, the constant rubbing of wooden stirrups, and perhaps even snakebites.

The first boots worn by actual 19th-century cowboys were modeled after boots worn by Hessian soldiers, who fought side-by-side with the British during the Revolutionary War.

Billy the Kid, though not a cowboy, was photographed in 1879 wearing such a Hessian-style boot, distinctive for its V cut in the front, pull-straps on the side, and leather or silk tassel (naturally Billy’s boots lacked this decorative touch). Other cowboys from this era wore variations on the Wellington, an English military dress boot that was actually a riff on the Hessian.

Sometime around 1870, a cobbler from Coffeyville, Kansas named John Cubine pushed the form further when he started making boots for Texas cowboys that, like a lot of footwear of the day, could be worn on either the right or left foot. These leather boots had pull straps, low heels, and roundish toes. They were also taller in the front to give the wearer more protection while making them relatively easy to get on or off.

By the 1880s, Hyer Brothers was just one of 100-plus boot makers in Kansas, while Justin Boots was probably the best known boot name in Texas. Sam Lucchese of San Antonio was right behind them, followed by Tony Lama and others. Kansas may have been where the whole thing got started (and even that’s not a certainty), but Texas is where the cowboy-boot industry was eventually established.

From the vantage point of the 21st century, the era of the cowboy seems to be a major part of U.S. history, but even by the turn of the 20th century, the cowboy was looked upon w...

With the advent of radio shows and movies in the 1920s and ’30s, the myth of the lone rider, driving his herd in hard country, was burnished until it gleamed. William S. Hart, Hoot Gibson, and Tom Mix were some of the early stars, and their appearance in cowboy boots of increasingly costume-like design in turn drove the design of these once simple boots to new, decorative heights.

Mix, in particular, was enormously influential. His boots were richly inlaid with contrasting colors of leather and silk stitching, and when he was killed in a car accident in 1940, it did not go unnoticed that like a good cowboy, he died with his boots on.

In the years since, boot makers have taken the simple template offered by the Hessian boot and used it as a canvas for every imaginable sort of decoration, using materials that go way beyond traditional cowhide.

Lucchese makes cowboy boots out of American alligator or lizard, in colors with names like peanut brittle and rust. Lama boots come in Caiman crocodile in almond or oryx. Loveless, which is one of many makers who has made cowboy boots for presidents, likes to work with ostrich, kangaroo, and elephant hide, while Caboots of El Paso has made boots out of cobra and python.

Then there are artisans like Dave Little, whose grandfather Lucien started the business that would become Little’s Boots in San Antonio in 1915. Little’s boots come in all variety of toe and heel styles, but it’s the burnished leatherwork that sets his boots apart. Little’s boots are like works of art, sold in pairs, featuring roses, eagles, flames, cactus, horses, and steer skulls in alternating shades of leather, ostrich, and you-name-it.

Rocketbuster of El Paso makes boots in a similarly exuberant vein, with designs ranging from pink boots decorated with cherries to curly-toe creations that look like they’d be worn by some sort of demonic court jester.

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