Frankly, dude, asking a barber about what hat to wear is sort of like asking a podiatrist about a rash on your face. But as it turns out, I am the right guy to ask—I love a good hat, and I think I can help you out here.
If it’s a chill sesh with the guys, then I don’t see a problem with a baseball cap, and these days, flat-brimmed caps are definitely in. If you have a smaller head, though, and the flat brim looks flat-out goofy on you, go with the rounded brim—it’s more athletic looking, anyway.
But if this is a formal affair, or the boss’s Fourth of July party, I’m going to say fedora. Yes, fedora.
And before you whine and groan and chant “Poser!” at me, I don’t mean just any fedora. I mean a snap-brim straw fedora, which is just formal enough to pass at any gathering. Not only is a straw fedora sophisticated, it’s also versatile. You can pop the brim up or down. If you have a smaller head, anything from a three quarter inch to a one and a half inch brim will work. If you’ve got a watermelon-size noggin, you’re going to need a little extra: one and three quarter to a two and a quarter.
Just don’t go too large on the brim. You’ll look like a cowboy, and that’s another column.
Shorty Maniace is the proprietor of J.P. Kempt Barber & Social in San Francisco. Send your questions to firstname.lastname@example.org.