The Fedora, and its little brother, the Trilby, are two of the most famous and timeless of all men’s hats. The Fedora features a wide brim, a hat-band or ribbon and a pinched and indented crown. The Trilby is similarly shaped, but typically has a shorter brim (and a tighter upturning at the back).
The Fedora first appeared in 1882 as a female hat. After 1924, when Prince Edward of Britain started wearing them, the Fedora was adopted by men and became part of their fashion replacing bowlers, flat caps and top hats.
The trilby was once viewed as the rich man's favored hat. The hat's name derives from the stage adaptation of George du Maurier's 1894 novel Trilby. A hat of this style was worn in the first London production of the play, and promptly came to be called "a Trilby hat"
Worn by Humphrey Bogart, Frank Sinatra, Cary Grant, Prohibition-era gangsters, Indiana Jones