The other night, I was over at my date's when I spotted a '40s-style hat shoved onto his bookshelf.
"Oh, my God," I said. "Is that a fedora?"
He stopped futzing around with his covers and sat up. "No?"
"It is!" I said. "Are you gonna take a selfie of you wearing it for your OKCupid profile? Do you think women should have an obligation to shave? Aren't you worried I'm gonna friend-zone you?" (This sounds kind of mean out of context, but dude linked me to Nice Guys of OKC, so he knows what's up.)
"It's not even a fedora!" he protested. "It's a homburg."
"It's a fancy hat, and therefore associated with jerkwads," I said. "I'm sorry, but you know it to be true."
Sometime in the last six months or so, people who wear fedoras have been smacked with the umbrella label of "Nice Guys" -- you know, the dudes who bemoan the state of gender relations when their would-be paramours choose the bad boy in the scuffed leather jacket over the one in the Mathletes cardigan. (It should be stated that all of my imagined man-woman relationship scenarios take place in an animated cartoon from the fifties.)
They also seem to have a tendency to equate "good conversation" with "guaranteed boning," which can lead to some awkward surprise!makeout scenarios. They're easily identified by their catchphrases, "Nice guys always finish last," and, "Can't she see that I'm the one who really gets her?"
I secretly think that we all go through a "Nice Guy" phase. I know that when I was 11 or so, I was super into telling my diary that all the boys with frosted tips in my science class didn't know what they were missing when they French-kissed the cheerleaders under the soccer bleachers. Most people, though, seem to grow a healthy self-deprecating streak by their mid-20s, making those who haven't seem all the more out of touch by comparison.
Considering all this, there's no question that "Nice Guys" are generally a pretty unpleasant crowd to consider dating. But for some reason, wearing a fedora seems to be up there with "identifies strongly with John Cusack's character in 'High Fidelity'" in terms of probable jerk factor. Among my friends, saying that a guy "has a fedora" is shorthand for "is going to try to guilt me into a hand job in exchange for a 15-minute discussion of 'The Princess Bride.'"
And they're not the only ones. FedorasofOKC, for example, has made a long-running joke out of the people (mostly men) who pair photos of themselves wearing fancy hats with statements like “Im [sic] an Atheist, and unless your [sic] either extremely liberal about your faith, or hot, then dont [sic] talk to me." Vice ran a story a few months ago about "Forever Alone Fedora Guy" who bragged about his hat collection being "bigger than average" immediately after detailing how his plans to stage a stealth orgy ended with two girls making out. Even the New York Times got in on the anti-fedora action, though they seemed more concerned with the hat's criminal associations than with its hypothetical relation to guys who think Daniel Tosh is funny.
As far as I can tell, the main problem seems to be with conflicting visions of self-image. Much like ugly eyeglasses and thrifted Christmas sweaters have become associated with people who have serious Feelings about vinyl, most people seem to interpret "guy in a fedora" as "dude who wants to put the minimum amount of effort into looking like he made an effort."
At the same time, because fedoras have been sported throughout history by men who were undeniably cool, dudes mistakenly think that wearing an Indiana Jones hat is license to expect every woman in town to write "LOVE/YOU" on her eyelids. And when that doesn't happen, they get sulky -- hence, the ensuing "Nice Guy" behavior.
Here's the thing, though: I have a serious boner for semi-formal wear. I can barely pass a person in a tie without wanting to twist my fingers in the silk and tug. My favorite thing to do to a tuxedo vest is slowly unbutton it. I once centered an entire erotic fiction scene around one character grabbing another by the suspenders that were hanging around his waist.
Even though I played it cool with my date's homburg because I knew he'd get the joke, I would have been totally into it if he'd slapped it on and given me flinty stares from underneath the rim.
And when I see a well-dressed dude or lady in a fedora, it immediately conveys "loose-cannon gumshoe who doesn't play by the rules." Therein lies the conflict: my crotch says yes, but my Internet Brain says maybe a jerk.
Say what you will about authenticity, but a fedora is a great way to jazz up an outfit and/or pretend that you're on your way to raid a speakeasy. Hence my love for them; despite my overall penchant for obstreperous loudmouths, there dwells somewhere in my fantasy hindbrain a strong-jawed, hooded-eyed dude in a seersucker suit who silently yearns to bring justice to the mean streets of my heart. I blame my father's insistence on watching "The Godfather" on a weekly basis during my vulnerable years.
And, because I tend to emulate the trends I find attractive, I also totally fantasize about rocking a fedora with some spats and cigarette pants as I solve crime using my sexual wiles. I know that the minute I break mine out, though, one friend or another is going to accuse me of moderating the more unpleasant 4chan boards. Sigh.
Ultimately, the jerkwad-fedora, like most stereotypes, relies upon public laziness for its longevity. Obviously, some dudes who wear fancy hats do fall into "Nice Guy" patterns. But to just assume that every haberdashery enthusiast is going to turn out to be a Men's Rights Activist is to do a lot of perfectly nice, would-be classy people a disservice.
Consider this, then, my official declaration: In 2013, I am going to stop allowing Internet memes to dictate my aesthetic preferences. When I see a person in a fedora reading a Raymond Chandler book on the train, I will not sneak furtive glances at them and then slip into the night for fear they are actually a dickhead.
Instead of biting my tongue, I will voice appreciation for a good porkpie hat if I see someone rocking one in the taqueria. And if I want to "borrow" a homburg in which I can skulk around town, I will ignore any naysayers who accuse me of "Nice Guy"-ing. Vive le fedora resistance!
If you have a tie on in your Twitter bio photo and you follow Kate at @katchatters, she will definitely take notice. Consider this fair warning.