Men in heels
This monarch made high heels fashionable for both men and women during the 18th century by declaring them off limits to everyone except the aristocracy. Naturally, people of every class were soon wearing them, but only the nobility were allowed to wear shoes with red heels (why red?).
This A-list actor has built a career on offbeat roles and swashbuckling adventure. Never afraid to blur gender lines in pursuit of a good performance, his portrayal of a transvestite (in what film?) is one of his most memorable.
Dressed for success
Even a leader of the free world likes to indulge in a little sartorial splendor now and then. This former U.S. president never made a secret of his preference for a stylish pair of heels above all other footwear.
Often cited as one of the finest actors of his generation, this movie star is known for roles as diverse as a confused college graduate on the make, a single father fighting to keep his son and a down-and-out con man on the mean streets of Manhattan, but he created one of his most memorable roles when he put on a wig, a dress and a pair of stilettos.
This legendary 12th century warrior and emperor (where?) proved that fashion can be practical, and that even brutal conquerors can have a soft side. An expert horseman, he wore distinctive red boots with wooden heels, which most likely inspired fear in his enemies and envy among his fashion-conscious troops, but certainly kept his feet firmly in the stirrups as he rode into battle.
These two actors were buddies back in the 1970s, until life took them in different directions. But they both got their start in a short-lived sitcom in which they played two struggling ad men who put on dresses and high heels in order to rent the only apartment they could afford — in a residential hotel for women.
Designed for notoriety
Demonstrating that high heels might just be back in style for men, this innovative designer of unisex, seasonal couture got the fashion world’s attention when he dressed his male models in heels (and wore a pair himself) at his New York runway show in 2009.
This actor from Hollywood’s Golden Age was considered quite a ladies’ man, but when he put on women’s clothing for a 1949 screwball comedy even his dashing good looks couldn’t make him into a lady. Even so, the acrobat turned movie star scored compliments from other men in the film for his shapely legs.
His successful transition from the vaudeville stage and radio airwaves to the small screen earned this comedian the nickname, "Mr. Television," and the title of "first genuine TV star." His weekly program (what was it?) was so popular nationwide (when did it air?) that the sale of movie tickets noticeably declined on Tuesday nights, the sale of television sets skyrocketed, and many restaurants, theaters and other business shut down during his broadcast hour.
This 5-foot-2 1980s rock legend is so crazy about high heels that he has high-heeled shoes or boots custom made to match every one of his outfits. Rumor has it that even his bedroom slippers aren't flats. When he isn’t tooling around town in his little red Corvette, chances are you can find him trying on shoes.