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The History of the Fedora

How the humble hat went from being a symbol of first-wave feminism to one of the douchiest things you can put on your body.

Jamie Peck

Jamie Peck

Image by Kat Aileen

Has any single article of clothing been more reviled in modern times than the fedora? From the bars of Brooklyn to the remotest corners of the internet, this short-brimmed headgear has become such a widely recognized symbol of douchebaggery, it's a wonder anyone is still selling them at all. In the minds of many, this simple accessory has come to stand for a certain type of mouth-breathing neck beard, the kind with a penchant for militant atheism, libertarian politics, and the men's rights movement.

Read More: The Broadly Guide To Men

And yet it hasn't always been this way; there are people alive today who can remember a time when the fedora was but a common headpiece whose main purpose was keeping sun and rain off the wearer's head in a visually pleasing fashion.

Where did the fedora come from? Where is it going? Where did it all go wrong?

Photo via Flickr user karl_hab

The Fedora Is in the Eye of the Beholder, or, a Fedora by Any Other Name Would Look as Fugly: Origins and Definition

According to the Online Etymology Dictionary, the term "fedora" originated in 1887 from a popular play in which actress Sarah Bernhardt played a headstrong Russian princess named Fédora Romanoff. The name Fedora is derived from the Greek word theodoros, which literally means "gift of God." (And you thought it was the hat of the devil.) As part of her costume, Bernhardt--who was known for cross-dressing--wore a slightly modified version of the "center-creased, soft brimmed hat" typically worn by men. As Bernhardt was quite influential in the women's movement, proto-feminists adopted the hat as a symbol of female empowerment and resistance to gender roles.

This hat bore only some resemblance to the fedoras of today. Which raises the question: What does "fedora" really mean?

I spoke with Sean O'Toole, the owner of JJ Hat Center, which was established in 1911 and is the oldest hat store in New York City. "That's part of the bastardization of the term," O'Toole explained when I asked about the original fedoras. "It was really the material of the hat that they were talking about [when they said 'fedora']. A fedora is really a soft, fur-felt hat. So anything you see behind you [in the store], no matter what the shape is, is technically a fedora. Even a cowboy hat is a version of a fedora."

"Originally you'd have these big open crown things that people would buy and turn into their own shape, which is what we still do here," he continued. "But what fedoras came to mean are these little wool or cotton short-brimmed hats, one shape."

While the word "fedora" is also frequently applied to the trilby and the homburg, which are two kinds of hat similar to the hat widely thought of as a fedora, this is not technically incorrect. As it turns out, many are walking around in fedoras unwittingly.

"People come in and say, 'I want a hat but I don't want a fedora,'" O'Toole said, "but in the end, what they end up walking out with is just the same thing."

Hatter's Heyday

Throughout the first half of the 20th century the fedora was worn by both men and women as a functional part of any well-dressed adult's outfit. Milliners modeled women's fedoras after the men's styles, using shirring and braiding to create a look for the "sophisticated female client," whose fedora was often crafted with brighter, richer colors and an upturned brim to avoid shadowing the wearer's face, according to the Metropolitan Museum.

Of course, the golden age of fedoras is not known primarily for female hat wearers, but for the well-dressed figures of masculinity immortalized by the concurrent golden age of Hollywood. From here on in, let us define the fedora as it was understood from this era onwards: soft felt material, short brim, caved-in top, pinched sides.

Many are walking around in fedoras unwittingly.

As the hat grew more prevalent among both men and women, its status as a women's rights symbol faded. As Robert Rath writes in the gaming magazine The Escapist, "the hat went from being a symbol of co-opted masculinity, to one simply considered masculine." Journalists, mobsters, hardboiled detectives, and politicians alike wore them as they went about their business, and ads like Stetson's depicted the hats as "part of the man." A man without a hat was just as castrated as a man without sexual organs, or so Madison Avenue's subliminal messaging implied.

A Kiss Before Dying

The 1960s ushered in some of the most sweeping political, cultural, and technological changes in US history, so it stands to reason the era would also change what people were wearing on their heads. The Greatest Generation continued wearing fedoras as part of their put-together looks while baby boomers began ditching hats for the more informal styles of the mod and hippie movements. Hat sales fell precipitously, while conditioner and hairbrush sales, presumably, climbed.

It's widely accepted that President John F. Kennedy singlehandedly killed the hat industry by declining to wear one during his 1961 inauguration. Wrote Suzy Menkes, now the international fashion editor for Vogue online, in a New York Times article dated February 27, 1994:

Now only two kinds of folk wear hats as a matter of course. There are those over 70 who find it hard to break a habit drummed in since childhood. They are the people who were shocked to the core when President Kennedy went bareheaded at his inauguration, ushering in a brave new hatless era. Jacqueline Kennedy's pillbox was probably the last hat to be universally accepted as fashionable.

And yet it's not difficult to prove this apocryphal. Rumor-debunking site Snopes points to numerous pictures of our 35th president wearing a top hat on inauguration day, and holds the drop in sales to be one of correlation, not causation-hats were already on the way out.

While it's true that JFK was reluctant to be photographed in a hat for fear it made him look out of step with the times, he nevertheless was spotted in headgear on numerous occasions up until his 1963 assassination. He may even have been the last widely popular heterosexual male sex symbol to be seen sporting a fedora for quite some years.

Ska: First Wave

The 1960s also brought an obscure subcultural movement that seemed largely irrelevant outside of Jamaica at the time, but which would turn out to have shockwaves that were felt for generations, musically as well as hat-wise.

After World War II, radios became widely available in Jamaica, bringing American rhythm and blues music to the population. Jamaican musicians combined these African American idioms with Caribbean calypso music to create ska, a uniquely Afro-American-Caribbean art form. Ska in turn gave birth to related genres rocksteady and reggae.

In a nod to American jazz and blues musicians, the rude boys of Jamaican street culture--heavily associated with rocksteady music--often sported fedoras, as well as their frequently confused relations, the pork pie and trilby. Community leaders criticized these disenfranchised (if well-dressed) youths for their involvement in petty crime and other social ills, bringing their headgear of choice down with them. (Little did they know that the rude boy's true badness would not manifest until decades later with the rise of Reel Big Fish.)

The Lost Years

Between the 1970s and the year 2000, fashion largely shunned the fedora in favor of long, flowing hair (the 70s), towering flamboyance (the 80s), and the rat's nests of grunge (the 90s). It's telling that one of the most recognizable fedora wearers of this time period--Indiana Jones--was a fictional character from a movie set in 1936. There were, however, a few notable exceptions. For much of Tom Waits's career, the singer-songwriter has accented his "timeless blues troubadour" aesthetic by wearing a fedora or similar hat. While Waits pulls off the look with ease, he also bears at least some responsibility for the countless fuckboys who have tried and failed to emulate him. And if Michael Jackson was the King of Pop, the fedora surely was his crown. Driven by his obsession with the golden age of Hollywood, Jackson could often be seen wearing one as part of his performance ensemble. On Jackson's head, the fedora transcended mere Prohibition-era cosplay and formed an essential part of his androgynous, theatrical style, complicating the traditionally masculine signifier significantly, if not outright queering it.

Ska: Second and Third Waves

After ska's initial wave came two primary revivals: 1) the Two Tone genre that was popular in 1970s England and 2) the phase typically designated as "third wave," which began in the 1980s and exploded in the 1990s. Two Tone acts like the Specials could be seen wearing all manner of hats, including the fedora, but were minimally offensive, perhaps because they had a strong connection to ska's roots and the social issues of the day.

If ever there was a point at which the fedora began to turn from simply out of to downright deplorable, it probably came with the wave of commercial American ska that crested with the breakthrough of No Doubt in the 1990s. While Gwen Stefani continues to pull off fedoras to this day--due in no small part to her aristocratic bone structure--the same could not be said of latter day ska-spawn like Sublime, Fishbone, the Mighty Mighty Bosstones, Save Ferris, and, yes, Reel Big Fish.

Don't Call It a Comeback

As post-9/11 conservatism reared its ugly head, a certain subsection of men vocally longed for a simpler time, one in which men were men, women were women, and abortion was outlawed in all fifty states. As a result, the fedora--and hats in general--began to creep back onto men's heads, in the pages of fashion magazines and paparazzi photos as well as the less sartorially advanced corners of the developed world.

In a New York Times article from 2007 titled "Old Hat? Not on a Young Head," David Coleman tracked the unfortunate trend of men using the fedora as an accessory accompanying less formal modes of dress, citing examples from Brad Pitt to various young urban professionals. The fedora began to be used as shorthand for "having a look" when often no look was present.

But the new fedora wearers do not pander to a '70s pimp-style costume instinct. These stingy brims and sky pieces (vintage terms for natty hats) are not meant as the crowning glory of a full-dress look. Rather, they top off more ordinary, but still snappy, modern styles: a hoodie, a crisp suit, a polo shirt, a shirt and tie. "A fedora goes with a lot of different styles, which is the way I dress," [Jive Records A&R manager Ant] Rich said. "If I am being conservative, it can make me look cool. Or you can have on a white button-up shirt and some plain jeans and sneakers, but if you have on a Rod hat, you're going to stand out. It's hip-hop and Rat Pack all rolled into one."

The Game: Penetrating the Secret Society of Pickup Artists

While the fedora was enjoying its brief re-entry into the realm of the fashionable, a writer named Neil Strauss was hard at work on what would become the foundational text for the fedora's terminal phase. In his book The Game: Penetrating the Secret Society of Pickup Artists, Strauss described the "seduction community," a loose group formed online and IRL by nerdy, socially awkward--and often white, middle class, and entitled--heterosexual men who gave money to self-styled "pickup artists," or "PUAs," in hopes of learning how to manipulate women into sleeping with them. Among more nefarious tactics like "negging" and "cat-string theory" was "peacocking": "a technique developed to get attention in busy, distraction-filled environments such as night clubs...by wearing something showy like a cowboy hat or a glowing necklace." Many men took this as a cue to wear a hat. Many of these hats were fedoras. In a paper titled "Fedora Shaming as Discursive Activism," Ben Abraham pinpoints a widely reblogged tip from a popular PUA forum:

"If you wear a hat, make it memorable, easy to spot, and something to work with your style. This is usually easier than it sounds. Try the fedora...it portrays you're a stylish man that knows what he's doing, and it's a great lock-in prop."

This was both a reflection of pre-existing fedoras and a catalyst for fedoras to come. An infinite feedback loop; a douchebag ouroboros.

Photo via Wikipedia Commons

The Great Shaming

As the 2000s became the 2010s and the internet became a major gathering place for feminist discourse, people--primarily young women--began using digital spaces as sites of resistance against white supremacist capitalist patriarchy as well as its token topper.

As chronicled in blogs like Fedoras of OkC (now defunct), the fedora was often correlated with the reactionary politics (explicit or implicit) of white, middle-class males who felt their position in society was being threatened by marginal gains made by women and minorities. Helmed by a young woman going by the handle "misandristcutie," Fedoras of OkC was particularly adept at pinpointing sexist or otherwise offensive statements made by these so-called "fedora bros" and publicly shaming them.

One ailment endemic to this group of fedora sporters was (and remains) "nice guy syndrome," i.e., the belief that if a man follows a certain set of rules, his desired mate should reciprocate his romantic or sexual advances. (A similarly named blog, Nice Guys of OkCupid (also defunct), popped up to chronicle this.) When faced with rejection of this belief system or assertion of female agency, however, the "nice guy" shows himself to be quite the opposite. In dating profiles across the world wide web, this anger could be observed positively seeping out from under the sides of any given fedora. "Omg what is it with these guys calling themselves 'gentlemen' or 'classy' because they own a fedora?" wrote one representative commenter on Fedoras of OkC. "I can smell the benevolent sexism from here."

In an article titled "Why the fedora grosses out geekdom," Leigh Alexander explains that "when women online who're fed up with online harassment and nice guy entitlement see an eager young man trying his best to strike a smooth pose under that infernal hat-pinching the brim, faux-brooding finger to chin and crooked smirk--we just see chasing ass."

It's important to note that the parties doing the shaming did not always intend to cast the fedora wearers from their company forever. Indeed, many women's frustration with these men could be traced back to the desire to find a male partner within a dating pool that contained an inordinate number of bad hats and worse attitudes. Hence, it was in their best interests to combat the culture that gave rise to the ill-advised headgear rather than exile these men completely.

Since medieval times, shaming has served to reintegrate the shamed party into society after a period of penance, and the Great Shaming through which we are still living is no exception. Later in "Fedora Shaming as Discursive Activism," Abraham writes that Fedoras of OkC was having some real impact, with a number of so-called "testimonials" of the effects of fedora shaming. One anonymous question asker [who'd been featured on the blog] left the following comment:

Oh hey I made the site. I'd like to confirm with you that I removed my fedora from my household months ago. Just never got around to up-dating the old page. <3 you guys for spreading the truth, ashamed I ever wore one in the first place.

Fedoras in contemporary pop culture

It's no coincidence that the fedora and its cousins have been featured prominently in several TV shows themed around toxic masculinity and the spiritual bankruptcy of the wage system. (Mad Men, Breaking Bad, and Boardwalk Empire being the big three.) As far as real people in fedoras go, I will let the examples speak for themselves.

Nevertheless, one notable outlier merits a final comment. While most people picture her with unadorned hippie hair, Yoko Ono's always been a fan of jaunty headgear. As she's ascended to her role as elder stateswoman of the arts, Ono has adopted the fedora as part of her habitual look, either despite or because of its dubious reputation. Ono has never been one to follow the rules, and if anyone can empathize with an unfairly maligned object, it's her. She usually tilts hers at a fun angle, as if to say, "haters gonna hate."