Fedoras are for jerks: a history of awful dudes in awful hats (2024)

Humans have always been very good at judging whether a dude is bad. In the European Middle Ages, you could probably tell because he’d always get way too hammered at whatever sad*stic cage-fighting event was happening in the town square. In the Victorian era, it was that one guy at the dinner party who was always jokingly diagnosing you with “female hysteria” every time you expressed an opinion.

Today, we have hats.

In the 21st century, a man’s hat has become shorthand not just for whether or not the wearer is garbage but for the precise kind of garbage he is. There’s even an early-ish (well, 2011) meme for this: Scumbag Steve in his trademark “A-tooth” fitted cap, denoting him as the sort of guy who comes to your party with five uninvited friends, pukes all over your couch, and bolts.

But the idea of the scumbag hat has existed well before memes. Way back in the mid-2000s, there was the fedora, worn by the dude whom you would talk to for a few pleasant minutes until he flew into a rage after you mentioned you had a boyfriend. Before that, there was the trucker hat, worn by the dude whom you’d talk to for a few pleasant minutes until he flew into a rage after you mentioned you find Ashton Kutcher insufferable.

Our current iteration of the scumbag hat might be the beanie — not worn baggy and over the ears like in the early 2010s, but instead plopped on just the very tip of the head, signifying to all who cross his path that the wearer is the type of guy who will throw you a “u up?” text only to leave you on read the night after.

To find out precisely why each wave of men’s fashion has its own designated “scumbag hat” and how an otherwise innocuous item of clothing becomes one, we tapped three constituents of #menswear — the internet-born community that’s blossomed in the decade since the rise of personal style blogs and that is largely responsible for the reason all dudes suddenly know how to dress: Lawrence Schlossman, the brand director at Grailed and the steward of the cult @Four_Pins Twitter; Jian DeLeon, editorial director of Highsnobiety; and Brandon Zaboklicki, better known by his username @sexualjumanji.

There’s a big reason hats have come to signify so much about a dude before he even opens his mouth: It’s because since the ’60s, and in part thanks to JFK, men aren’t really obligated to wear hats in public anymore. These days, a dude wearing a hat — specifically one that doesn’t serve a functional purpose — is often purely superficial, and we’re a lot more likely to judge a man for wearing something solely because he thinks it looks cool than we are when a woman wears, say, stilettos.

Of course, that’s not to say we don’t judge women for their sartorial choices — in fact, part of the reason hats might not have the same outsize significance for a woman’s personality or style is because there are more important physical things to judge her on: her body, the way she does her makeup, or how she speaks, for instance.

“Really, hats serve a very basic utility,” says Schlossman. “It’s to cover your head from the elements, whether it’s sun or rain or snow or whatever. And while almost every garment in the history of clothing has been created to serve a very clear utility, as clothing has modernized, now hats are real estate — it’s a billboard and signage for the wearer to actually say something about themselves or their personality.”

To be fair, there’s nothing intrinsically wrong with a fedora, or a beanie, or a trucker hat. But as DeLeon puts it, douchebag hats “become douchebag hats because douchebags wear them. The hat itself wasn’t douchey.”

“It’s like people getting the fascist haircut ’cause everyone else has it,” adds Zaboklicki. “I think the hats just get associated with a certain group and it goes from there.”

But how?

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As their name would suggest, trucker hats became a thing because of truckers. The baseball-like caps, with their mesh backs and foam fronts and emblazoned with a company logo, were popular as promotional items in rural American businesses, which would give them away to the truckers who passed through.

“I was still a child and people that wore trucker hats always seemed creepy to me,” writes Zaboklicki on the topic of trucker hats. It’s a pretty apt description, considering the trucker hat trend started out of somewhat of a conspiracy to place them on the heads of every single celebrity of the early 2000s.

“Those hats specifically took off because of Christian Audigier,” explains DeLeon. Audigier, a French fashion designer who had moved to Los Angeles, “essentially bought up all the rights to [Von Dutch and Ed Hardy], and he had the right industry connections to get them on celebrities who would wear them.”

And before “influencers” was a household term, hugely popular celebrities were pretty much the only people who were randomly photographed wearing outfits for all the world to see. “Where all trends begin and end is with celebrities and influencers,” says Schlossman. “Men and women alike, kids, adults, whatever, are clearly influenced by celebrity culture. But I think for men, specifically, there’s this idea of the archetype, and that, I think, is a way that a lot of guys dress — in this aspirational way that is connected to an archetype.”

Unfortunately for us, the archetypes of masculinity in the early 2000s were people like the lovably scummy Ashton Kutcher and Kevin Federline. But what replaced the trucker hat was possibly even more sinister.

Jeff Kravitz/Getty Images; Jeff Kravitz/Getty Images; Frazer Harrison/Getty Images

Fedora-like hats in the early 20th century were often worn by both sexes. But it’s the men of the 1920s through the ’50s — business executives, gangsters, detectives, journalists, and the Hollywood stars who played them — who would end up creating the idea of the fedora as a distinctly masculine item.

You can pretty much blame Justin Timberlake for the comeback of the mid-2000s. Even though all he was trying to do was bring sexy back, instead he ended up bringing back the sartorial equivalent of Pepe the frog.

All three of our menswear experts agreed that the fedora, despite being a classic, holds terrible connotations. “I think the fedora has gotten the worst rap out of all of them,” says DeLeon. “If you were ever going to find a picture of what an internet troll looks like and a men’s rights activist looks like, they would definitely be in the middle.”

“If you saw a f*cking dude wearing a fedora on the street, where does your mind immediately go? This dude loves to go to co*cktail bars on the weekend and is an amateur mixologist and is an incel on Reddit or whatever,” says Schlossman. And despite the fact that Zaboklicki wears them himself, he says, “Even today whenever I wear one, I’m like, ‘God, I look stupid.’”

But why? DeLeon says because the fedora is such a classic, men wear it expecting to appear gentlemanly. “It was the whole thing of expectations versus reality meme, right? I feel like for a lot of guys, the fedora was targeting the classic sort of ’60s Mad Men, Don Draper era. The execution couldn’t have been more off for a lot of these guys that were wearing it.”

Justin Timberlake, Ne-Yo, and Johnny Depp, all of whom were popular in the mid-2000s, were all channeling the old-school dapper aesthetic to some degree, but it was also simply a dark time for menswear in general. “Keep in mind, it was the same era where you can go to Urban Outfitters and buy a blazer with a hoodie sewn inside. Justin Timberlake wore that look heavily,” says DeLeon. “He literally looked like Dave Chappelle’s crackhead character from The Chappelle Show.”

Dark times, indeed — that is, until we moved to the totally opposite direction.

Ray Tamarra/Getty Images; GotPap/Getty Images; Christopher Peterson/Getty Images

As America’s financial system crashed and the new decade loomed, hipster lumberjacks invaded the concrete streets of cities like New York and Los Angeles, bringing the knit toques of the Canadian wilderness with them.

Beanies “are supposed to convey this semi-stoner, relaxed, California ‘bro’ type,” says DeLeon. “It was this way of communicating that you’re a relaxed person — saying that you don’t care too much but care enough.”

As Zaboklicki describes them, “Beanies always look like they want to talk about the new camera they just bought.”

The perennially easy joke to make regarding the beanie is about the people who wear them when it’s not actually cold out. But as Schlossman argues, prioritizing form over function is basically the entirety of what fashion is.

“As life modernizes and arguably function becomes less of a necessity in modern life, then you can completely lean into form and just wear something as an aesthetic choice,” he says. “If you like the look, that is clearly more important for these people than actually staying warm. Looking cool is more important to a lot of people, myself included, than necessarily being warm.”

Though the beanie has been somewhat of the scumbag hat of the past decade, there have been two sharply distinct ways of wearing it: sagging off the back, or rolled up tight.

“What’s interesting to me is that maybe two years ago, the big thing was the slouchy beanie, very much that kind of look where it’s sagging off your head like a f*cking reservoir tip on a condom or a wizard hat or some sh*t. That was the de facto douchebag LA or New York guy beanie,” says Schlossman. “It’s funny how the beanie itself has stayed consistent, but the look has shifted from that kind of sagging, sloppy nature to now we’ve been talking about a much more rolled-up, tighter [look]. It resembles more of a yarmulke than something else.”

If the old slouchy beanie look was for guys who wanted to appear laid-back, the new tightly rolled beanie — helixing, as some have called it — is for the guy who’s more self-aware about his scumbag tendencies, as one viral tweet articulates:

It would be easy enough to claim that in the year 2018, it’s impossible for men to wear hats without emitting at least some degree of scumbagginess. But it isn’t! “I think this fear of being a poser has been washed away a little bit and people are taking risks and trying things out,” says Schlossman.

“And the really cool thing about a hat is for the most part, hats aren’t crazy expensive. You can buy a fluorescent yellow or orange Carhartt beanie for 30 bucks, maybe even less. And you can try it and see if you get compliments and see if your significant other likes it or whatever. When you can take that risk with hats, it’s easier to experiment and try something out and see if it ultimately is going to work for you.”

Plus, even #menswear gods are guilty of fashion blunders sometimes. “I feel like if you were involved in that scene in the 2000s, you had one of those Che Guevara military-style caps. I bought one from a surplus store and haven’t touched it,” DeLeon admits. “I think I wore it for three months and I was like, ‘This is not me.’”

He does, however, caution against one thing: “If you’re trying to have a little bit of classic menswear in an outfit, don’t do the hat.” After all, even Don Draper was kind of a scumbag.