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For all the jokes about game journalists and their fedoras, I can’t actually recall seeing a colleague wear one. Oh, I’m sure they exist, and I’ve been to PAX enough times to have seen the odd snap-brim or trilby bobbing around in the wild, but even when the infamous Yahtzee visited Escapist Expo last year, his trademark Trilby seemed to stay at home (Though he briefly experimented with cat ears). But since the meme about nerds and their fedoras doesn’t seem to go away, I figured the topic warrants enough public interest for a discussion – so screw it, let’s talk about why nerds wear fedoras.

To understand the fedora’s appeal, you have to go back to its origin as a costume piece in the 1882 play Fédora. Sex-symbol actress Sarah Bernhardt sported the hat in her title role, and on its debut the fedora became the new “in” fashion among young women. But saying the fedora started as “a woman’s hat” ignores one crucial aspect – from the start the fedora represented assertiveness and more than a hint of masculinity. Sarah Bernhard liked to wear men’s clothing, and she alternately scandalized and titillated Victorian audiences by playing male roles like Hamlet and, in a particularly incendiary production, Judas Iscariot. (In this version, Judas betrayed Jesus because he’d “stolen” Mary Magdalene, who was the lover of both Judas and Pontius Pilate. Seriously, read up on Sarah Bernhardt, she’s awesome.) Due to the fedora’s linking with a public figure who was assertive, sexually liberated and took on masculine roles, the women’s rights movement adopted it as a symbol and from there it spread to women in general. It finally ended up as a hat of, after an advertising push, men in cold weather climates who needed a hat to keep the rain off them. From there the style became ubiquitous, but is especially associated with film stars like Humphrey Bogart and Frank Sinatra, and gangsters, who appreciated that the hat could withstand the elements while obscuring their faces. In other words, the hat went from being a symbol of coopted masculinity, to one simply considered masculine. While phased out of everyday fashion by the 1960s, it remained a staple of period films like Indiana Jones and a testosterone-boosting accessory for celebrities like Johnny Depp and Michel Jackson who don’t fit the traditional masculine mold.

In other words, ever since its inception the fedora has been a symbol, though originally an inverted symbol, of what it means to be male. Men who wear fedoras tend to see it as a callback to an older age of style, but it’s also a way to engage in fashion without appearing fussy – a reaction to an upbringing that more often than not told them that caring about their appearance or dressing in nice clothes made them seem a derogatory “gay.” This coincided with looser trends in men’s fashion through the ’80s and ’90s – decades where being a “suit” became another derogatory term, and dressing down connoted authenticity. While men in 1950s and 60s TV shows dressed impeccably, by the ’80s the fashion-inept husband became a running gag. Meanwhile, office dress standards fell across most professions as Baby Boomers took the helm, to the point that even traditionally conservative professions like lawyers and news anchors stopped wearing ties. Casual dress might’ve led to comfortable work environments, but it also raised a generation of men who felt uncomfortable around fashion – now that’s changing.

It’s no accident that in the last decade we’ve seen an explosion of shows, from Mad Men to Boardwalk Empire that depict characters being fashion conscious while retaining their masculinity. Not coincidentally, these shows packed with tough men in snappy suits all take place in the past, with all the distance that affords. These shows provide an outlet for men who are interested in clothes, but retain the worry that this makes them appear feminine. Clinging to yesterday’s most iconic hat is a way to assert fashion sense without worrying about public perception.

Unfortunately, wearing a fedora often has the opposite effect, coming off as a desperate grab at confidence by someone who doesn’t know better.

frank sinatra fedora

Trying to wear a hat is a phase many young men go through, but it’s understandable when you consider that other men’s accessories like cufflinks, tie clips, school rings or watches are about as formal and outmoded as the fedora. While certain subcultures continue using these items, in most high schools, colleges and workplaces these would be seen as preppy or even useless. Watches may look impressive, but smartphones have been our primary timekeepers for over a decade. The tech industry, highly influential in the geek community, is particularly hostile to anything that appears formal. This has created a confusion about what wear is appropriate at what time, and left young men grasping at straws when they try and create a “look” for themselves. In other words, the black fedora has come to symbolize men who’re insecure about how they look but want to stand out from the crowd.

It’s sad, really. American men’s fashion is a wasteland at the moment, partially because most men are afraid to venture too far from established norms. Go to South America and you’ll see men wearing bright colors without thought that it’d impinge their sexuality. Hit a club in Hong Kong and you’ll see more than a few sporting a Mandarin collar shirt or suit jacket. India retained its historical love for lush patterns. America, though, is still tied to conservative cuts and monochrome blacks and blues. Given that, I can’t blame anyone for trying to jazz up a dull wardrobe with a flashy hat – and frankly, I get a little weary of seeing fedora-wearers get made fun of for doing that.

However, on the other hand, that doesn’t mean there isn’t an epic misuse of the fedora going on, mostly by people who – as I’ve said before – might be young or not fashion-conscious enough to know the difference. The fedora’s a great hat, but it isn’t for everyone and it needs to be integrated with someone’s outfit.

A fedora, for instance, is a dress hat. Yes, I know that there are all sorts of fashion mashups these days – especially in the game industry – where people wear blazers over Mario tees, but this is different. Fedoras were designed as a suit accessory, and they look out of place when worn with a rumpled t-shirt. It’s like tucking a pocket square into a polo shirt, or wearing wingtips with shorts. You can’t really dress down a fedora, and unless you’re prepared to wear a suit with it it’s going to look out of place. And that’s another problem – unless worn very well, the fedora is such a throwback that it looks like a costume piece. Unless you’re a Hasidic Jew, they’re no longer considered daily wear. James Bond hasn’t worn them since Roger Moore, and if men’s fashion has one law, it’s this: when Bond stops wearing something, it’s no longer in style.

There are logistical issues as well. Hats may make sense outdoors, but inside remove they’re a nuisance – always hogging space on restaurant tables or perching on your lap. Hats going out of style meant the infrastructure that supported them, like racks and cloakrooms, disappeared too. This leaves modern hat-wearers with the option of either breaking etiquette by wearing a hat indoors or standing around, holding it in the hand or under the arm. Neither option is attractive nor practical.

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Then there’s the issue of hat selection. Too often men make the mistake of choosing a hat they like, rather than one that looks good on them. Not every man can wear a trilby in the same way not every man looks good in vertical stripes or boxy glasses. A hat should compliment your head and face shape, and the color should do the same for your skin tone. Black, for example, might look too severe on a light-skinned person – particularly paired with a black coat.

And yes, if you’re wearing a fedora – especially a black one paired with a trechcoat or a dressed-down look – people may assume negative things about you. Women have largely pegged this uniform as belonging to the so-called “nice guys” that think being decent to a woman is a ticket into her bed. I’m sorry about that, but it’s true. (For what it’s worth, I asked two women outside the gaming community what kind of men they associate black fedoras with. Answer: Creep, avoid immediately.) Clothing is a representation of ourselves, and if you’re wearing clothes that are associated with a particular subculture or stereotype people will, fairly or not, form an impression based on those clothes. It’s true that wearing a fedora doesn’t make you a Reddit-dwelling Men’s Rights Activist in the same way that popping your collar doesn’t make you a bro, but in both cases you’re taking a risk by adopting the stereotype along with the style. About 50% of fashion’s social function is to influence how others see you, and the impression a fedora creates often isn’t positive – if you didn’t know about this stigma, you do now.

However, fashion’s other half – I’d argue the most important half – is about influencing how you see yourself. And you know what? If wearing a fedora makes you feel good about yourself, do it. I wear one at my desk on occasion, an Indiana Jones model my wife got me for my birthday. It doesn’t suit my face and I’d never wear it in public, but it reminds me to live the adventurous life I’ve always wanted. (Though I can tell you from personal experience fedoras perform poorly on an archaeological dig.) Sure the fedora’s an extreme fashion statement, but in a culture that considers cosplay to be appropriate attire for a con-goer and even celebrates it as body-positive, I don’t see why, if done properly, fedora wearing should be a cardinal sin. Both attempt to craft the self into an ideal form.

So to those that would judge the fedora, I say: I understand. There’s certainly overlap between the self-proclaimed “nice guys” of the internet and the fedora fanbase. But ridicule is a poor motivator for personal change, and it would be more productive to target the problem behaviors rather than fashion choices.

To those that cleave to their hatbands and snap-brims, I urge you to do what makes you happy – I’m not here to police your body. But also know that wearing a hat is a bold fashion move that carries inherent risk that you’ll look behind the times or even come off as a stereotype. If you do want to wear a hat, buy it at a decent shop, since they’ll help size it properly and find a color and style that compliments your appearance. Hats are fun, and there are hundreds of styles to choose from, so don’t feel boxed into one look. Try a pork pie or a Panama, experiment with colors and materials. After all, if you’re going to make a fashion statement that bold you might as well wear something different than, you know, everyone else.

For my part, I’ll stick to scarves, good shoes and the occasional watch.

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