We are in the midst of a hat crisis. The one go-to hat, the Fedora, has been coopted by douchebags. So what's a guy to do? Going hatless is not an option for those of us whose hair has turned its back on us. Here is a guide to the pros and cons of men's hats.
Get most people to draw a hat and chances are it'll be a Fedora. It's got enough of a brim to provide sun protection, it can be worn with the brim up or down, and it's just an all around good hat.
Worn by: Don Draper, Indiana Jones, Malcolm X
Pros: It looks great with a suit or nice blazer. If you can pull one off, you actually look quite sophisticated.
Cons: It's becomes associated with douchebags. I think that's unfair, because what most of the douchebags are wearing is...
The Trilby is the stunted cousin of the Fedora, and it, not the Fedora, is the kind worn by Reddit types. Fun fact: both the Fedora and the Trilby were originally ladies' hats.
Worn by: Ska band members
Pros: It's slightly more casual than the Fedora.
Cons: There's the douchebag thing, plus it provides little sun protection.
A great casual hat that keeps the sun out of your eyes while playing sports. Gives you a slightly boyish look.
Worn by: Baseball players (doy), golfers.
Pros: You can take it off and shove it in a coat pocket and it won't lose its shape
Cons: Should never, ever be worn with a suit.
A flat topped hat with a wide, round brim. Makes you look like an extra from Guys And Dolls.
Worn By: Buster Keaton, Johnny Depp in Benny and Joon, jazz musicians.
Pros: Is a playful, fun hat that nonetheless looks dressy. Looks great with a suit or with jeans. Makes you feel like you're in Guys And Dolls.
Cons: People will be asking you for meth.
Stetson is actually a brand name that makes several hats, but it has become synonymous with the cowboy hat. A tad big, but some guys can pull it off.
Worn By: Cowboys, both genuine and urban, country singers, Lawmen.
Pros: Combine it with a bolo tie, a Nudie suit, and some nice boots, and you're looking fine.
Cons: People will call you "Sheriff."
Don't even think about it.
The Flat Cap
Related to the Newsboy cap, a nice, casual gentleman's cap that nonetheless looks more dressed up than a baseball cap.
Worn By: Street urchins from the 1800s, English farmers, Tom Waits.
Pros: Goes well with a cardigan and a nice pair of slacks.
Cons: May cause you to develop a Cockney accent.
The Top Hat
The ultimate formal hat. Originally made from beaver pelts, now mostly silk or synthetic.
Worn By: Magicians, Willie Wonka, Flavor Flav, Slash
Pros: As close as you'll ever get to looking like Fred Astaire.
Cons: Sooner or later someone will slap you with a white glove and then you'll be in a duel.
A cute little hat that is possibly the most British piece of clothing imaginable.
**Worn By: Charlie Chaplin, Malcolm McDowell in A Clockwork Orange (Fun Fact: the bowler is worn by Quechua women in South America, and was also popular in the Wild West)
Pros: Highlights one's impish qualities.
Cons: Statistically more likely to comically blow away in a strong wind._ (Note: I have been told that this is not literally true. Cartoons have lied to me._)
And, by popular demand, two late entries:
Named for the city in Morocco where they make the red dye for the hat, a cylindrical hat with a tassel. Related to the African Kupi, which is usually more colorful.
Worn By: Sydney Greenstreet in _Casablanca_, English magician Tommy Cooper, 900 year old TimeLords.
Pros: Apparently, they're cool.
Cons: You may be mistaken for a Shriner.
One of the most versatile brimless hats, it's worn by military groups as well as snooty intellectuals. One of the few truly unisex hats, it can also be thrown in the air in feminist triumph over the knowledge that you're gonna make it, after all.
Worn By: Mimes, Che Guevara, Girls coming back from their senior year trip to France, freaky beatniks,
Pros: Through clever color-coding you can show your allegiance to French existentialism/black power (black), U.S. Special Forces (green), The U.N. (Blue), or Prince (Raspberry).
Cons: Facing the wrath of Gallophobes who probably want to rename it a "freedom lid."