How to Pull Off Wearing a Fedora

Actually, I have no idea. But that doesn’t mean I’m giving up
Daniel Guidera

At one point in my life I stocked up on fedoras because I didn’t want to be unprepared for an apocalypse in which Frank Sinatra returns to Earth and extinguishes hell’s hottest cigarettes on the faces of the unready. If I was wearing a fedora, he might pass me by.

Problem is, fedoras are out, and have been since the Kennedy administration. Two years ago, I asked Jenn Grabenstetter, Charlotte magazine’s fashion editor at the time, whether I could wear one. Her response: “There is no fashion advice more enduring than this: just say no to the fedora.”

Whatever, Jenn. What do you know? You only followed fashion trends for a living. But you’re not down here on the streets with me and Kevin Federline.

I don’t wear my fedoras much anymore. Overall, I’m a much snappier dresser now, but that’s only because my wife has basically thrown out every article of clothing I bought on my own. She’s trying to save me from myself. I had a really nice silky Hawaiian shirt once. It bore a print of these guys down in the water, using a net to catch fish while palm trees swayed in a gentle breeze. I’m sure Goodwill didn’t even put it out in the showroom. They probably boiled it down for glue.

Charlotte is perhaps the most fashion-conscious place I’ve lived, but that’s not saying much. I grew up in small-town Ohio (hoodies!) and lived in Columbus (Ohio State hoodies!) and lived in West Virginia (hoodies under Carhartt jackets!). I’ve never had to reside in New York City or Los Angeles, places where you could have two noses and not horrify people so long as you were wearing a nice blazer. Charlotte is somewhere in the middle of those two extremes. Khakis send a signal that the bank you work for supports casual Fridays, a suit means you’re a narc, and it’s probably too warm to wear a hoodie anyway. I see fedoras out there. In Plaza Midwood they wear them with wallet chains. Uptown, they wear them with an ego.

I had a really nice silky Hawaiian shirt once. I’m sure Goodwill didn’t even put it out in the showroom. They probably boiled it down for glue.

I called Jenn to ask if fedoras had come full circle. She said, “Ehhh,” and then stumbled through a long, belabored explanation. I caught every third word or so: dapper … vest … bow tie … metrosexual … 1912. She’s still bearish on fedoras. “It’s striving for irony but not getting there,” she said. “Anyone who wears one looks like they’re kidding.”

Which is one of the Three Ways A Man Can Get Away With A Fedora Nowadays. You have to wear it like you’d wear a trucker hat: with a sharpened, hipster-like sense of GET IT?—the equivalent of winking at everyone you see. Or, she said, you’d have to own it. I would have to wear a fedora everywhere every day, which means I’d also probably have to start chewing on a cigar and writing about boxing and saying I was buds with Bert Sugar. Or, the third option, I’d have to wait for nature to ravage my youthfulness. According to Jenn, old men in fedoras are just adorbs.

But there is hope. Two years ago, fedoras were dead. Now they’re only mostly dead. Even a mostly dead fashion can come back around if you give it enough time. And if I can just age quickly enough, I can wear one with my hoodie and I’ll leave my wife speechless. Just speechless.

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