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Fashion in Action: Embracing Man’s Worst Accessory

Can I wear a fedora without looking like a complete douche? I brought one to the Kentucky Derby to find out

How the hell am I supposed to pack this thing? I thought to myself, staring at my freshly purchased fedora.

I had no intention of keeping this accessory long-term. My plan when I bought the ridiculously overpriced, much-maligned hat earlier that day was to wear it for a few hours at the Kentucky Derby that weekend, fly back to Los Angeles with it and return it to the men’s shop for store credit.

But as I alternated my gaze between my already-packed suitcase and my new hat, I realized there was no way to pack the thing without ruining its shape and return value. If I really wanted the hat as part of my Derby ensemble, I’d have to wear it while traveling — in the Uber to LAX, through the security line, on the plane and back again on my return trip.

My first experience wearing a fedora wouldn’t be within the comforts of the Derby, where wearing otherwise obnoxious hats has been normalized. I would have to wear it in the wild, without irony as a shield. I was about to embrace a sartorial lifestyle I actively despised; I was going to become a Fedora Bro.

There is simply no way for a basic white dude such as myself to wear a fedora without looking like a complete tool.

Fedoras were once a staple of masculinity. A requisite accessory to any business suit in the 1960s, they communicated a sense of class and sophistication. Not to mention, cool: there’s also an association between fedoras and the criminal underclass of the early 20th century.

But whatever gentlemanly mystique fedoras had in the Mad Men era has long since eroded and been replaced by an undeniable lameness. Many incorrectly attribute the demise of the fedora — and formal men’s headwear, in general — to John F. Kennedy not wearing one to his 1961 inauguration. But JFK did wear a hat that day; he just took it on and off throughout the day. Truth is, hat sales were already in decline by 1961 as more young Americans began rejecting conformity.

Now, fedoras are for affected douchebags who are desperate to seem sophisticated, but who lack any true elegance. They’re the height of hipster pretension. Fedoras are for white men too lazy to forge interesting personalities. (The only exceptions are jazz musicians and Justin Timberlake, and even he just barely pulled it off.)

So, yeah, I’m not much of a fedora guy.

But I was headed to the 142nd running of the Kentucky Derby, “The Most Exciting Two Minutes in Sports,” which, save for a few obscenely wealthy horse owners, is really just a celebration of Southern gentility. The acceptable attire for the event might be described as chic Georgia garden party. The women don sundresses and ornate hats, and the men wear seersucker, madras, pastels, bow ties, pocket squares and hats of all stripes. If there was ever a time to experiment with a fedora, it was this.

My fedora journey began on Abbott Kinney, a short stretch of unbearably hip bars, shops and restaurants in LA’s once-bohemian Venice neighborhood. Abbott Kinney has become the epicenter of Venice’s swift gentrification in recent years, so if there was anywhere to buy a fedora, it was here.

The store clerk at the men’s shop did little to hide his displeasure in my fedora taste. He kept pushing me to buy the white and blue Buster Keaton-style pork pie hat, but I wasn’t trying to look like a vaudeville comedian. Instead, I opted for the camel brown fedora with the cream band because it matched the belt and shoes I planned on wearing.

He also took issue with the way I chose to wear it (on the back of my head, slightly tilted up) as opposed to pulled down and fully covering my brow. He had no problem taking my $50 for the headpiece, however, and I suspected he’d try to foil my plan to swap the headwear for a couple T-shirts the following week.

The fedora was the last thing I grabbed before hopping into my ride to the airport. My driver didn’t comment on it, nor did anyone at the airport.

The thing about wearing a fedora: You quickly forget it’s there. The fedora became just another piece of clothing I was wearing, doing my best to tune out other travelers and hustle through security.

But a fedora does have great functional value while traveling. You can turn it over; place your wallet, keys and other pocket items in it; and send it through the X-ray machine as your own, personalized security container. Once on the plane it served as a nice cushion for my head against the back of my seat. Oh god, was I enjoying my first fedora excursion? I immediately took it off when I reached the hotel on Thursday night and didn’t put it back on until two days later at the Derby. There was no way I was wearing it while going out at night.

I was to that some women even like fedoras. Or at least some of the women who attended the Kentucky Derby this year, as I received three unsolicited compliments on my outfit (crisp white, crewneck T-shirt; royal blue chinos; seersucker blazer; Wayfarer Ray-Bans; and light brown shoes, belt and … fedora).

The experience reminded me of reading Neil Strauss’ The Game and hearing pick-up artists espouse the virtues of “peacocking,” dressing like a total idiot to attract the attention of women. The idea is that women will be drawn to any man with a distinct sense of style, no matter how silly he looks. You might remember Mystery, the pick-up artist extraordinaire, who would appear in public wearing black leather pants, tons of rings, pilot goggles and oversized, faux fur hats.

But the Derby is a tough place to gauge the effectiveness of a fedora, as many men wear them there (including two other people in the bachelor party I was with). I was surprised and relieved when a female bartender complimented my fedora the following afternoon. I was eating brunch alone, killing time before my flight when she said, “I like your fedora.”

And it happened again on the plane ride home. I struck up a conversation about Game of Thrones with the platinum-haired woman sitting next to me, and I felt compelled to tell her, “I don’t always wear a fedora, by the way. I just couldn’t fit it in my bag.”

“Really? I thought it was working for ya,” she replied.

I was flattered, but all this praise wasn’t enough to convince me to continue life as a Fedora Guy. They are too closely associated with a certain type of internet bro: the anti-creationist, Reddit-loving brony who wants to talk to you about ethics in gaming journalism.

My fedora experiment will live and die with the Derby. I just hope that store has a liberal return policy — this hat is filthy.

John McDermott is MEL’s staff writer. He last wrote about the decline of the nickname Dick.

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