Of the men’s hat types, trying on the right one is, quite possibly, the most important hat-decision that you may ever make. Hats are haircuts without the commitment. Head-attics like these are Excalibur and you are King Arthur. Take a leap of faith and place these skull palaces on your think-chamber. Embrace your hatted alter-ego. Just make sure to wear a baseball cap—in between trying these on—as a palate cleanser. Anyone and everyone should try on the following men’s hat types:
1. Top Hat
The absolute, main reason to try on a top hat is the novelty factor. It’s been worn by people like Slash, Abraham Lincoln, and Brenden Urie. Feeling like a sir can’t be attained without placing one of these on your head. It doubles as a storage unit: you could hide so many things up there. This is where magic rabbits live like hermit crabs. These hats can animate snowmen. For any short guys who feel uneasy about wearing heeled shoes, this is the other direction to take. Uncle Sam wants you to try one on and so do I.
2. Cowboy Hat
Try this one on with caution: while wearing a cowboy hat, one is a cowboy. For everyone who’s ever wanted a mustache but couldn’t grow one, this is the mustache of the men’s hat types. The 10-gallon hat is worth a try in itself, even if its name is a downright lie to the general public.
It’ll keep the sun out of your eyes while you’re watching a rodeo. Lasso yourself some second glances by tipping your hat to everyone who comes within 60 feet of you. Doff your hat and bow if you see a fellow cowboy. If the hat fits, you may have what it takes to tame horses and become a stripper, in that order.
3. Pork Pie Hat
Named after what could objectively be described as gross, the pork pie hat is worth trying on for its simple elegance. Alas, it’s not a bacon hat unless Kevin Bacon wears it. That’s not to say that you couldn’t sew in a bacon-shelf. Buster Keaton famously wore this hat while silently slapstick-ing through the streets. Don one of these and invent a seedy, mastermind persona like Walter White and become a respected but feared member of your community.
Trying on this hair pillow might make you feel awkward at first, and it should. Let that feeling fade, and take a look in the mirror: you look better than half of all fedora wearers. No better of the men’s hat types can be worn while serving one’s opponent on the dance floor. The wide-brimmed version of this hat is essential to Indiana Jones’s existence and ostensibly worth risking your life over, in order to maintain your chic. Cool has never felt so criticized.
5. Bowler Hat
One of the men’s hat types with two names, the person who pulls off the derby in the most unique way is Brian Viglione, drummer for The Dresden Dolls (an über-glorious band that occasionally does reunion tours). Get a cheap cane to feel what Charlie Chaplin felt like when he lost a Chaplin-lookalike contest: confused. Be the anachronism you were meant to be and place this bad-boy atop thy head.
6. Bearskin (Military) Hat
The only of the men’s hat types that doubles as a wig for your hair: this hat was meant to be tried on. An authentic bearskin cap is one giant, fury, phallic device made from straight up, hardcore bear. Consecrate your manhood by placing this on and having someone Houdini-punch your appendix. Of the men’s hat types, authentic bear hats run into the hundreds.
If serendipity shines on you and someone lets you try one on, take the opportunity to soak in the experience for all it’s worth. The most notable cadre to wear this massive, midlife crisis on their heads are the members of the Queen’s Guard. Taking one of their hats is not advised, but don’t let that stop you. Other ceremonial military groups around the world have them, including the United States.
Even if you don’t think one of these will look right, try it on anyway. Don’t let the peanut gallery tell you what you can and can’t try on.