As a fashion object and symbol, the high heel shoe is weighted with meaning. It’s also weighted with the wearer’s entire body weight. The stiletto might be one of the only designs that is physically painful but has somehow has persisted for centuries. At their origins, high heeled shoes were originally worn by men. As early as the tenth century, many horseback riding cultures wore heels on their boots and on their shoes, because heels help you stay in the stirrups (which is why cowboy boots have heels).