THE NAPOLEON

Popularized By: Napoleon, naturally

Hat Story: Napoleon was known for his tall. Folded-brim felt hats. Some hypothesize, in fact, that Napoleon is remembered as short because his gigantic hats dwarfed the rest of him.
Pluses: The last guy who wore it conquered most of Europe.
Minuses: From a distance, it looks like a giant possum is asleep atop your head.

THE BERET

Popularized By: Saddam Hussein (president, Iraq) and Max Fischer (president, Rushmore Beekeepers Club).
Hat Story: Originally worn in ancient Greece and Rome, the beret reached the Basque country by way of traders. The Romans color-coded their berets (white, for instance, could only be worn by aristocrats).
Minuses: Also looks French

THE FEZ

Popularized By: King Hassan II (King of Morocco in the 1960s) and Shriners
Hat Story: This visorless, flat-topped, betassled felt cap became part of the official Turkish dress code under Sultan Mahmud II in the 1800s and remained so until being outlawed in 1925, two years after Turkey became a secular republic.
Pluses: Friends and family will be able to spot you in a crowd: “Just look for the tassel!”
Minuses: Won’t keep the sun out of your eyes; people will start calling you Fezzy McTassleman.

THE BOWLER, AKA THE DERBY

Popularized By: Charlie Chaplin (who played a dictator in The Great Dictator) and Benito Mussolini (who played a dictator in World War II)
Hat Story: Originally designed as a kind of stylish hard hat, the narrow-brimmed bowler first appeared in 1850 and for the next several decades was the hat for those who though top hats pretentious—or expensive.
Pluses: Much sexier than today’s hard hats (if also less hard)
Minuses: It didn’t work that well for Duckie in Pretty in Pink.

EGYPIAN DIADEM

Popularized By: King Tutankhamen (of Egypt) and Steve Martin (of Saturday Night Live)
Hat Story: Tut’s royal crown, made of gold, glass and semiprecious stones, featured a vulture and cobra (representing goddesses of lower and upper Egypt) to protect the leader. Martin’s was made of plastic.
Pluses: It’s good to be king!
Minuses: Airport metal detectors

THE TOP HAT

Popularized By: Abraham Lincoln (16th president of the United States)
Hat story: A Cantonese hatter designed the first silktop hat in China for a French dandy back in 1775—but top hats didn’t catch fire until the 1820s. Honest Abe actually wore a variation on the top hat called the stovepipe hat, the hat being straight rather than wider at the top.
Pluses: Uber-retro, and black is very slimming.
Minuses: Kids always asking you to pull a rabbit out of it.