By Horus Alas

It’s a hat with a soft brim, a crown pinched on both sides to give it indentations from its peaked center in the front, and commonly, a band running around the base of the crown. From about the 1920s to the 1960s, it was a ubiquitous item of menswear. At one point or another, everyone from legendary mobster Lucky Luciano to President Franklin Delano Roosevelt wore one.

It was a “man’s” man’s accessory. You wore it at the bar when you were ordering a neat whiskey, and you took it off when you sat down at the poker table to play Texas Hold ‘Em with your boys. You wore it with your suit, tie and pocket square in the rain, and you radiated an immediate, effortless, classic cool.

That’s what the fedora was known for, anyway. My recent acquaintance with it includes its use by Don Draper and Roger Sterling in AMC’s iconic series, “Mad Men.” And yes, the characters who wore fedoras in that show were dashing and debonair.

Since the emergence of this meme circa 2012, however, the fedora has become a symbol for socially awkward, creepy men who have no semblance of an idea how to act around women. The accessory has undergone a transformation of the kind Franz Kafka told us about in “The Metamorphosis:”

“One morning, when Gregor Samsa woke from troubled dreams, he found himself transformed in his bed into a horrible vermin.”

It’s a tough break if you’re Gregor Samsa and you suddenly wake up in your bed as a repulsive insect.

But let’s bear in mind that a fedora has no agency. It’s a fashion accessory, and it’s only as well-regarded or disdained as the individual who wears it.

What seems to have happened then, is that the fedora was co-opted by a far less reputable crowd than the Don Drapers or Frank Sinatras of the world.

The second Urban Dictionary definition for the term “fedora” reads:

“In present times, the fedora is a trademark of the socially inept beta male. He is attempting to distance himself from pop culture with the distinct style of past fashion. But he captures none of the suave, and only comes off looking like an oblivious, pompous fool. This is especially the case when it’s a low-quality fedora coupled with unfashionable clothes and an unkempt appearance.”

Images abound of the more contemporary, awkward-as-hell wearer of today’s fedoras. There’s this guy and this guy and this guy. Buzzfeed compiled a list of 20 reasons to not date today’s fedora-wearing men.

Noor Al-Sibai of the late feminist blogging outlet Feminspire wrote on fedora wearers, “Often, they don’t even need to be given the chance–these fedora’d ‘nice guys don’t respect women nearly as much as they claim they do, and definitely don’t respect their disinterest or their consent (or lack thereof).”

As Sibai aptly notes in the title of her post, however, “The Fedora Isn’t the Problem—The Men Wearing Them Are.”

In today’s culture, the well has been poisoned against the fedora. This once-exalted accessory that crowned the dome pieces of individuals as fly as Humphrey Bogart or Dean Martin now seems to be predominantly worn by men complaining about being “nice guys” who can’t get a girlfriend.

For the most part, it’s the ethos associated with it—not the accessory per se—that has proven so damning to the fedora.

We could at this point veer off into another conversation here altogether; that is, what is a “nice guy?” Why do women seem perpetually uninterested in him? Is it true that, as the purported “nice guys” claim, women are always irrationally drawn to players, douchebags and assholes who constantly break their hearts?

These questions aren’t central to the inquiry at hand, but they at least deserve a gloss here.

What is generally meant by a “nice guy” is not so much a man with a generally-pleasing, affable demeanor, but rather someone spineless who bemoans his misfortunes and lack of success with women. Their woes and travails are often self-inflicted—a result of this selfsame spinelessness.

The second, blistering definition of the term “nice guy” on Urban Dictionary reads:

“Men who spend their most of their time whining about how women ‘just want to date jerks.’ Oblivious to the fact that no one finds people who feel sorry for themselves attractive, much less people who blame others for their lack of success. Most self-proclaimed ‘nice guys’ are just as self-centered and misogynistic as the jerks they gripe about, they are just much more spineless.”

You could easily write a book about the collective “nice guy” phenomenon, the insidious culture associated with it, how its ethos leads to outright vile recriminations of women, etc.

But back to my main focal point here—the fedora.

What have they done to you, you poor, beleaguered hat? Do you identify with Dante in the “Inferno” when he laments, “There is no greater sorrow than to recall our times of joy in wretchedness?”

You, who were once radiant and sparkling like the effulgent, spangled stars in the heavens—how did they so swiftly drag you down into the pits of hell?

It happened in my own lifetime. I watched this artifact that once epitomized men’s style crash and burn abjectly like a wayward clump of asteroid into the unforgiving mantle of the Earth.

We know what the fedora represents today, and its status is lamentable.

But we also know what it once was. And though the odds are dramatically against it, the fedora can once again come to represent the suave panache of a Lucky Luciano or a Dean Martin.

It’s 2017, and although fedoras are now mostly known for being worn by disreputable men with poor attitudes, they can also be worn by this guy and this guy and this guy.

There remains something inherently cool about this accessory that can add a nice dose of élan to a well-structured outfit worn by a well-structured man. What remains is for the wearer to make it respectable once again.

Featured Photo Credit: Courtesy of Rachel Chapdelaine’s Flickr account.

Horus Alas is a freelance writer and can be reached at

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