Image via Complex Original
Somewhere along the way, I became a "hat guy." Not a cap guy, or a beanie guy—though I’ve got no beef with either style—but a man who wears proper, brimmed hats with some degree of regularity. You know—hats befitting of an adult.
There are plenty of hat people in the world. Among the most prominent, Pharrell, Theophilus London, Indiana Jones, and street style fixture Justin Doss. There are also part-time hat guys, like LeBron James and Harry Styles. All have received their fair share of praise and criticism for their choice in headwear. Dressing outside the baseball cap isn't easy, and it really does take some getting used to—it's no longer the '60s and there's always the risk of looking more like a "fedora dork" than a bona fide "hat guy."
When exactly this happened, I can’t say. That’s because, like disappointing your parents with your life choices, transitioning from non-hat guy to hat guy doesn’t happen in one fell swoop. It’s a process, one that’s filled with small realizations, inevitable missteps, and the occasional teachable moment. Here’s what I’ve learned in the course of my journey.
Self-consciousness is not your friend.
OK, sure, “confidence is the key to pulling off any look” and all that, but really, when it comes to wearing a hat—especially in the early stages—it’s less about feeling like a boss and more about being willing to ignore the fact that people are looking at you. Because people are looking at you. Most men don’t wear hats anymore, so you’re a novelty. If that’s going to make you uncomfortable, probably best to just stop now.
Don't let the hat wear you.
Trying to build a look around your hat is a fool’s errand. Just think about that insufferable guy slinging drinks at the cocktail bar that everyone calls a “speakeasy” (despite the fact that it has a liquor license and is completely legitimate). You know, the one that dresses in high-waisted tweed trousers and suspenders, with a trilby teetering atop his head. He kind of looks like an asshole, right? It’s because he’s in costume. You shouldn’t be.
You can't just throw a hat on with anything.
On the other side of brim, you want to avoid looking like the other kind of idiot in a hat: The sad-sack, mom’s-basement type wearing a pair of crappy jeans and a worn-out logo tee, but topped off with what he refers to as a “fedora” (but is probably a trilby). Also a hat fail. If you put on a hat and it feels unnecessary, it probably is. Take it off.
It's all about the high-low balance. White tee, denim jacket, slim trousers, and Stan Smith sneakers? Yeah, you're probably good. Camel topcoat, sweatshirt, slim jeans and Chelsea boots? Also seems like fair game to top it off with a hat. Pulling off a proper hat should feel like the icing on the cake. So don't put good icing on a crappy cake.
Understand your look—and how a hat plays into it.
I have a relatively formidable beard. And I live in Brooklyn. Which means that if I wear a black hat, I don’t look unconventionally dashing so much as I look like a member of the prominent Hasidic Jewish community in my neighborhood. Which is kinda cool because they look swaggy most of the time, but I do have to be mindful of the fact that my headwear choice will land my heathen ass in the Mitzvah Tank before it grants me passage to the inner sanctum of some swanky party. Take stock of your personal style quirks, and be aware of how your hat interacts with them.
Stop worrying so much and just go for it.
Honestly, the trick to working a hat into your day-to-day rotation is that there’s no real trick at all. Just wear one — preferably one that’s made from fur or wool felt, and doesn’t come from a mall. There will be trial and error. Sometimes, you’ll feel like an idiot. Other times, you’ll feel like you’re crushing it. And when the latter starts happening more often than the former, you’ll know you’re doing something right.