There are a lot of dorky-looking hats out there, so pay attention.

Hats that are, ultimately, wrong for you, as a man.

There are as many ways to go wrong with a hat as there are hats, times the number of men, minus the number of proper hat/man combinations.

1. You must wear the hat, and not the other way around. Unless you’re lucky, you’ll have to try on a lot of hats. Don’t feel bad about this, not even if the salesman gets huffy or the saleslady has to climb to the top of her ladder to get your size off the very top shelf. They just want to sell a hat and get you out of there, you want to avoid looking like an ass.
2. There are also local cultural associations to consider. In Vienna, for example, if you wear a derby (bowler) hat, you’ll look like a coachman. Because the men driving tourists around town in the horse-drawn carriages all wear derby hats, including the women.
3. Maybe it has something to do with one’s aura, too. If you have the strong rock-star vibes, you can maybe get away with a top hat, for example. Normally, the top hat will wear you, unless you are, for example, a female goth, or something like that.
4. YMMV
5. Also, Indiana Jones ruined things for that hat he wore, honestly.
6. I would advise trying, for starters, a narrower-brimmed black hat to avoid too much of the Indiana Jones/gangster thing. There is the unfortunate Blues Brothers association, but in general, you can’t go wrong with a medium-brimmed black felt fedora.
7. Homburgs are nice, too, but expensive, sheesh.
8. If you wear a Homburg to a ball, for example, and it comes back from the coat check all smashed up, I bet you’d be upset, whereas if your black felt fedora comes back smashed up, you’re also upset, but not as upset as if it had been a Homburg.
9. A medium-brimmed black felt fedora is also versatile. With the brim down in front you have the urban/e older guy thing, if you are wearing a dark suit and coat, and if the brim is turned up, you have the klezmer musician/halleluja I’m a bum/Yogi Bear thing.
10. Also, don’t carry too many metal things in your pockets, especially, say, six USB sticks or a one-handed pocket knife, even if it is a tiny one, because it could happen that you want to get into the UN to renew your ID, and that you discover, once there, that a new security system has been implemented, say, requiring you to pass through a metal detector and x-ray thing and you have to spend ages emptying out your pockets and going, Gosh, had I known I was coming I wouldn’t have brought all this junk, and, whoops, what’s this? And all the bored gigantic Slavic security guards standing around will suddenly perk up and look at your teeny knife and say, Oh, look! A WEEPON. He has a weepon. And you say, maybe, Can I leave this here and get it after? Because then, after you do this, and go through the metal detector, you’ll stand there putting all your stuff back into your pockets, and it will sound less like a reprimand and more like a request when you say, Excuse me, officer, your x-ray machine seems to have eaten my hat. And it will take them a while to find it, because black felt is apparently nearly invisible in the dark interior of an x-ray machine, but when it does roll out, a little crumpled, you will think, at least it is not a Homburg.