Celebrating men with hats

Hats are the ultimate accessory for the head. Hats can keep your head warm or keep the sun out of your eyes. Hats look good with a suit or with shorts. Hats can even be an extension of your personality, an expression of who you are as a person.

Take it from me, a man of many hats.

Many famous people over the years have worn hats as a fashion statement or as a personification of their character.

I’m not famous, but I choose to wear hats, almost on a daily basis. I wear mostly fedoras, panama hats, baseball hats and beanies. But I’m open to any hat, if it looks good and fits on my rather large head. I would like to encourage others to embrace the hat, after all what other apparel can change the way you look so dramatically and give you new personality.If you are struggling to think of what style you might adopt the following is some famous people and the hats they wore (or did the hats wear them?)

Fedora hat

Famous for his whip and his fear of snakes, Indiana Jones had many on-screen adventures, always wearing his trademark fedora.

Harrison Ford had the right scruffy, masculine look to pull off wearing the hat, whether it was in caves and hanging onto the back of a moving truck.

Other famous fedora wearers: Freddy Krueger, Dick Tracy, Tom Landry, Michael Jackson

Bowler hat

Also known as the derby hat, coke hat or billycock, the bowler hat’s most famous wearer was silent film star Charlie Chaplin as “the Tramp.”

Chaplin appeared in over 80 titles in his career that spanned a half-century, but he didn’t go far as “the Tramp” without his trusty bowler on his head.

Other famous bowler wearers: Oddjob (Bond villain), Butch Cassidy, Billy the Kid, The Riddler

Top hat

Top hat wearers know that chimney pot, stove pipe, cylinder and silk hat are other names for the hat that Abraham Lincoln wore while president of the United States.

Honest Abe was already over six-feet tall, and his famous black top hat made him a giant of his time and ours.

Other famous top hat wearers: Tom Petty, Slash, The Cat in the Hat, Fred Astaire, Mark Twain, Winston Churchill


There are many types of beanies, from tight skull caps to looser styles that hang casually.

Ali G (Sasha Baron Cohen) wore a tight yellow beanie all the time, never showing us his hair.

The style was popular with school boys in the 1920s, but those caps came with a propellor on top (not cool nowadays).

Other famous beanie wearers: Tweedledee and Tweddledum, Orthodox Jewish men, Colin Farrell

Cowboy hat

A gaucho is a Mexican cowboy, and the most famous gaucho hat wearer was Zorro.

But the most well-known cowboy hat wearer had to have been John Wayne, the great film actor who dubbed cowboy hats “the hat that won the West.”

Other famous cowboy hat wearers: every country music star, Ronald Reagan

Red hat

Santa Claus is the only fictional person to wear this hat.

Other famous red hat wearers: not famous, but many other drunken uncles around Christmas time

Deerstalker hat

Guy Ritchie didn’t get the memo, and neither did Robert Downey Jr.

Sherlock Holmes is the most famous deerstalker wearer. In fact, he had the monopoly on this specific hat. No other famous person wore this hat, fictional or real.

Other famous deerstalker hat wearers: real Sherlock Holmes look-alikes everywhere

Wide-brimmed Yellow hat

The Man in the Yellow hat was also the only person, real or in fiction, to wear a wide-brimmed yellow hat. But it’s worth mentioning, if only for consistency.

Other wide-brimmed yellow hat wearers: no one in their right mind

Coonskin cap

Known as a traditional piece of Native American clothing, Daniel Boone and Davy Crocket (‘king of the wild frontier’) popularized this ugly hat.

Essentially, it’s like wearing a whole raccoon on your head, tail and all. If it’s 40 degrees below, fine. Not in Cayman, though. Please no.

Other famous coonskin cap wearers: William Clark (of Lewis and Clark), Jebediah Springfield (from ‘The Simpsons’)


Napoleon had, well, as Napoleon complex, so he wore the bicorne (or bicorn ro cocked hat) hat to add a few inches, or so they say.

Other famous bicorne wearers: other small people?


Johnny Depp as Captain Jack Sparrow in Disney’s movie adaptation of the Pirates of the Caribbean theme park ride is the only adult human to wear a tricorne in the last 300 years.

And he made it look good.

Pirate’s Week in Cayman brings out the other tricorne fans, but no one does it like Jack.

Other famous tricorne wearers: Frederick the Great

Sailor cap

Many distinguished service men and women wear this hat everyday while they take up arms and protect their country’s borders, but it’s a silly TV star that made this cap famous.

Gilligan got lost and the sailor cap was found. And no one else in the civilized world ever wore one on an island. Only Gilligan.

Other famous sailor cap wearers: Jack Nicholson in The Last Detail



The hat company with the tiny kangaroo logo was made famous by the countless interviews and film roles of the great Samuel L. Jackson.

Kangol must pay his mortgage, car payments and kids’ college tuition, because he wears these hats everywhere he goes.

And he looks like a bad motha every time.

Other famous Kangol wearers: Brad Pitt, Arnold Palmer, LL Cool J


Most people that think of berets think of the French, and rightfully so. But there are many types of berets.

The most famous beret wearer had to have been Che Guevara, the Marxist revolutionary. But Rastafarian also wear berets, just a different kind, to put away their dreads.

Other famous beret wearers: Bob Marley, Fidel Castro, Henry VIII, wannabe film directors and artists

Baseball cap

Every baseball player in the world wears a baseball cap to work — now think about that.

But the baseball cap became popular head ware for average citizens like Steven Speilberg and Jay-Z. You know, just average multi-millionaires trying to blend in with everyone else.

Other famous baseball cap wearers: ah… everyone at some point of their lives