The fedora draws increasing controversy in internet circles. In just one hour I found no less than three Tumblrs related to shaming people who wear the creased, curve-brimmed hat—formal with a touch of classic dandy—and the censure is interestingly specific. The targets are usually men.

The fedora draws increasing controversy in internet circles. In just one hour I found no less than three Tumblrs related to shaming people who wear the creased, curve-brimmed hat—formal with a touch of classic dandy—and the censure is interestingly specific.

The targets are usually men. Nerdy men.

Although one of the sites, You Shouldn't Wear That Fedora, chides the fashion-oops on men and women alike, the relatively-new Fedoras of OKC (where "OKC" means popular, endearingly-awkward dating site OK Cupid) focuses strictly on geeks who've made the choice to crown their search for love with the offending hat. Usually the humor derives from a presumptive consensus: that the fedora-wearers think they look much more suave than they do. Profile snippets, presented out of context, are often caption enough.

Fedoras of OKC doesn't strictly limit its lambaste to the dapper caps. Once-weekly, it offers Top Hat Tuesday, when it's time to pick on fans of the geeky "steampunk" trend, like this cog-topped gentleman who lists Japanese cartoons and comics alongside his predilection for dominance sex play. It's such specific nerd-bullying that one starts to wonder: Is there some kind of correlation between earnest, romantic-if-awkward geeks and a blind faith in the appeal of classical hats?

A third Tumblr, Forever Alone Fedoras, correlates the hat fetish with the "Forever Alone" internet meme, born for high-volume forum users to tease one another about how their preference for online socialization and dorky interests will mean they might never find love.

This meme has an extra layer of mean. It's supposed to be "funny" that online geeks are even trying. In one incident, a flash mob was staged, using fake OKCupid profiles, to humiliate those who turned up. The explosive Cheezburger network is on top of the trend: its Meme Dates site relies on the pairing of sincere romantic hopefuls—fedora optional—with internet idiosyncrasies to humorous effect.

The concept of awkward men seeking online love appears to create a resentment issue for the women who end up fielding that search. Like Fedoras of OKC, Forever Alone Fedoras is apparently run by a woman fed up with the relative frequency of messages on dating sites from men wearing "these horrible hats that are an instant deal-breaker."

Says Forever Alone Fedoras: "a fedora speaks volumes about one's character. It implies that he is a basement dwelling, live action role playing, no social skills having, complete and utter geek in the worst sense of the word."


So, some of these guys are a little awkward. But what's with the virulent derision? Especially since these Tumblrs and Fedora-memes tend to take a knowing tone, curated by people who come from the same world as the people they're mocking.

Just a glance at Forever Alone Fedoras, for example, generally requires you know what a Brony is, or at least net-literate enough to know what "duckface" means, to get the jokes. Why hate on your own kind? Hasn't everyone been picked on enough? Shouldn't geeks unite?

Well, yes, but that was before a great war in geek culture began. The internet has long been famously hostile to women: well past the turn of the millennium, an entire genre of online humor relied on the idea that there were no females on the internet.

Type "there are no women" into Google and see the results. Many of Google's suggestions relate to baseline geek culture stuff, presumed to be closely associated with the average geek's online experience. Like the internet, comic books, video games and lore-packed science fiction/fantasy also have a spotty record when it comes to being safe, or welcoming, for female participants.

Now, though, with the rise of social media, women are losing their fear of being shamed or shouted out of participating in arenas once seen as boys' clubs. The rise of women on the internet coincides with the rise of women in just about everything, as an election year that has politicized birth control and motherhood (and made headlines out of gross misconceptions about rape) encourages more women to speak up about their experiences and claim their right to social equality.

Geeky girls need to fight. When, in the year 2012, even the New York Times publishes an article about harassment in gaming culture, you know you've got a problem – just as fans of other nerdy things often experience similar social dynamics to gamers.

One part of this battle, however, is not about facing down direct aggression or exclusion. It's a quieter fight against "nice guys"—gentlemen who are trying really hard, but who feel entitled to appreciation and attention because they've met a basic standard of human decency.

From them, one finds no overt verbal abuse or leering hostility. Instead, interests are found such as pickup-artist forums and other venues offering advice on talking to girls or support for dealing with unrequited crushes—the raw material for all those Forever Alone jokes.

Being nice is a desirable trait. However, thoughts that begin with "I'm nice, therefore you should…" are creepy for reasons that should be obvious. Just look at this XKCD comic, or this advice column, or this.

Inside the "nice guy" complex seethes a passive-aggressive fear of the so-called "friend zone." It's such a prevalent concept in internet culture that yes, there's a (mean) meme for that. There's even a bizarre Kickstarter up right now for "friend zone t-shirts," and it's hard to tell who exactly should wear them. Feel unlucky in love? Why not let everyone know! The creator says the shirts will take a "stand" against the issue, but a logical throughline for that thought remains evasive. Take a stand against who?

The undertone of entitlement inherent in the "nice guy" concept scares women who want to go online or attend conventions without all the uncomfortable pickup lines. Women hope to make geeky friends without fearing to hear, one day, the phrase "remember how you said I was such a great friend?"

Friend zone. Forever alone. And here we return to the fedora.

The problem is that the fedora has become a go-to accessory for a peculiar subculture of love-entitled male nerds whose social inexperience and awkwardness manifests in a world rocked by a gender revolution—a tectonic shift in the makeup of formerly cloistered, rule-bound clubs. They aren't bad people – they simply need a place from which to draw a sense of manhood, if not from women. When deciding how to represent themselves in a dating profile, why wouldn't they cling to a fashion emblem from a bygone age, a time when guy was just a guy and a doll was just a doll? A fashion which recalls Frank Sinatra and Al Capone, a conventional masculinity marked by elegant detachment and an appeal to women that remains decidedly independent of their approval?

The fact that so many consider the fedora a personal "signature" item, added to Twitter avatars and self-portraits on DeviantArt alike, lend credence to this idea. Ben "Yahtzee" Croshaw, a game reviewer at The Escapist popular for his snarky humor and penchant for going against the grain used the trilby as something of a logo: a sharp-brimmed hat suggests a sharp wit, a certain whimsy and mystery.

But we geeks are late to the fedora party. The hat, often in plaid, made the same rounds through "bro" culture already, popping up on viewers of Jersey Shore and Entourage. Also, Jason Mraz wears one.

Conscious of culture and history as we are, we yearn for a touch of class. But 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 become too intentional, too choreographed, too staged. It seems to hide something. It suggests inner conflict.

The person who started Fedoras of OKC goes by "misandristcutie" on Twitter, a good-humored dig at men who cry "misandry" in any gender conflict, pointing to some imaginary universe of female privilege so feared as to justify their sexist behavior.

Even if you disagree with the hypothesis linking the forever-alone fedora and the friend-zoned nice guy, you can at least see why it explains the high volume of mockery aimed at the hat—and why some defend it in militant tones usually reserved for explaining the right to make rape jokes.

There's one more interesting tidbit. According to the Encyclopædia Britannica, "fedora" came into parlance when Sarah Bernhardt played the title character in Fédora, an 1882 play by Victorien Sardou. That sort of felt hat was a women's fashion item, and did not become popular among men until the late 19th century.

Funny—a hat emblematic of privilege-denial in geekdom wasn't even cut for dudes.