If you’ve watched enough Westerns, especially those shown in movie theaters in the 1950s and before, you could be excused for thinking that the hats and boots worn in those movies were what cowboys actually wore in the days of the Wild West during the latter half of the 19th century.
Nothing could be farther from the truth. Back then, riders wore whatever hats they happened to have. Derbies and Civil War-style hats were especially popular. The cowboy hat as we know it today did not exist, and cowboy boots, if worn at all, were either work boots or the Wellington-style boots favored by those who rode English style.
Western-style hats and boots evolved over several decades. The first 'cowboy' hat was invented by John Stetson. It was called 'Boss of the Plains', and featured a wide rim to keep the sun out of a rider’s eyes and to keep the rain from dripping down his or her neck. Western-style hats, as we know them today, were mostly influenced by the styles worn in the movies, although Stetson and other brands definitely played a role.
As far as boots are concerned, modern cowboy boots evolved from the English Wellington boot and the boots worn by Mexican vaqueros. None of the early boots had the pointy toes that are fashionable today. Pointy toes serve no useful purpose, although someone once said they were useful for stepping on a spider that is trapped in a corner. You can blame the movies for the pointy toes. With respect to the decorative aspect of cowboy boots, the Mexican cowboys, or vaqueros, were chiefly responsible for the fancy filigree work and other adornments, but the Western movie heroes, including Roy Rodgers, Gene Autry, and the Lone Ranger played an important role in popularizing the fancy footwear we see today.