5 Things You Learn While Trying to Pull Off a Wide-Brimmed Hat as a Grown Man

Image via Complex Original

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. 

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. 

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.

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. 

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.