The cowboy boot style didn't emerge until the late 19th century. Cowboy boots borrowed from historical English bootware designs, including the designs for the Wellington boot, the Hessian boot, and the Coffeyville boot. The original cowboy boots featured small heels (about one inch high) and plain unadorned leather. Later versions displayed more ornamentation, such as a V-cut down the front of the boot. Other boots featured tassels.

Cowboys from Texas sometimes inlaid the Texas state symbol, the Lone Star, in their boots. As the boot-wearing tradition evolved, American cowboys began adopting the European Cavalier style. This featured better manufactured leather and heels with slightly more lift. The original cowboy boots offered only rounded toes. Pointed toes were not adopted until the middle 20th century.

Starting in the early 20th century, cowboy boot designers began adding stitching on the toes of their wares. This stitching was functional; it allowed the boots to flex at the toes. However, designers soon started to ornament and decorate based on the toe stitching. During the late 1920s, cowboy boots became popular with fashionistas on the West and East Coasts.

Thirty years later, thanks in large part to the proliferation of Wild West stories on radio and TV, cowboy boots emerged as a major 'fashion hit' around the country. Today, boot makers, such as Luchesse, Dan Post, and Justin, manufacture hybrid boot designs featuring special ergonomic soles. Country line dancers inlay their boots with rhinestones and studs. Other companies, like Ariat, produce boots especially for equestrian activities.