How long was it before cowboy boots became successful?

Answer 1

Cowboy boots were created as a working tool for the Spanish horse mounted livestock herders called Vaqueros in the middle ages (possibly as early as 1000 AD). They did not have to become successful. The same with the cowboy hat and the rest of the cowboy "costume".

When Mexico became a Spanish colony the Vaqueros came too to herd the livestock brought over from Spain and brought their clothing with them.

When the northern parts of Mexico became U.S. territory the Vaquero's boots, hats, etc. were renamed.

For what it is worth, the "vaqu" at the beginning of Vaquero is a Spanish word derived from "vacca" of Latin and means cow or cattle, so the English word cowboy can be considered a translation of Vaquero from Spanish to English.

The conversion of the cowboy boot (etc.) from a work boot only worn by those doing that type of work to modern fashion clothing began in Hollywood movies of the 1920s and 1930s that popularized a fantasy of the cowboy lifestyle (although the real cowboy life had completely died out shortly after 1900).