How do you show your personality in a room full of billionaires, each of whom can afford as much designer fashion as they care to buy? Try a baseball cap.This week, members of the tech and media elite ...

There’s also the fact that a backwards cap helps emphasize a man’s facial features rather than covering them up: “It’s going to accentuate the lips, the nose, everything,” Hitchcock says.

1860: The baseball cap evolved to a longer brim and deeper, button-top crown, first worn by the Brooklyn Excelsiors. 1901-1902: The Detroit Tigers became the first team to put their mascot on its cap.

The end result was pure perfection: the style looked cute, it stayed in place all day long, and it was easy to master. This has replaced my normal go-to baseball-cap styles, and it's a trick I've ...