The fedora is not Monica Lewinsky’s sex-guerrilla beret made sweet with a bow, taking no prisoners with an infantile feminine twist. Nor is it Mary Tyler Moore throwing her beret to the sky—You’re gonna make it after all. We are not sure whether we’re going to make it, in a fedora.

The single woman wears a fedora to say, I want a man who is like a woman in a hat.

Jemima Kirke as Jessa on Girls.

Paris was the first to wear the fedora in the way of my thinking, but feels, as founders of a line sometimes do, like a decoy. Her adoption of the men’s hat wasn’t a bellwether so much as an accident, something she happened upon in her personal experiments with costume. Every day was Halloween for Paris. She was literal about social uniforms, and knew how to sexify them according to the rules of her own personal drag: sexy navy, sexy newsboy, sexy farmer, sexy cowboy. Familiar dress was cropped, ripped up, bedazzled, and always topped off with the attendant hat. On Paris, the fedora was sexy Fred Astaire, with a touch of Michael Jackson—something about how the brim offset the narrow slope of her nose, or how she managed to look like a wax replica of herself without appearing dead, as Michael, even while living, looked embalmed. Paris was literal, but the way a dream is literal: a walking wish fulfillment swathed in symbols so obvious they’re comic. All unconscious, she carried the therelessness of Los Angeles in her strut. It took someone with as little nuance as Paris Hilton to bring back the men’s hat as a symbol of modern female sexuality and confused morals. A subtler person would have chosen something else.

Lindsay’s hat was not this way—and to me, the hat began with Lindsay. I would like to know which Hollywood stylist put a fedora on Lindsay Lohan’s head because I think that person is a genius. Lindsay first began to appear in hats after the first cycle of her eating disorder, post-rehab, during her lesbian relationship with Samantha Ronson. It was Lindsay’s funny way of saying that she was the femme—because of course Ronson, a DJ with a UK skater-boy thing, would always out-butch her: tight pants, big shoes, greasy hair tucked back, vampiric dark circles. In photos Samantha was always snarling like a tough orphan, though under the soot and freckles you knew she had nice parents. Instead of just wearing lipstick to imitate a woman, Lindsay wore a fedora to imitate a man imitating a woman—imitating, more specifically, a sort of closeted ’50s homosexual whose excessive display of formal masculinity revealed how much of life was costume. On Lindsay the hat said: Yes, I am experimenting, but not in the way you think. Also: leave me alone. This is an essential quality of hats: they announce one’s desire to be unannounced. A hat is an advertisement for a disguise.

Lindsay courted the paparazzi with her hats, padding around West Hollywood like Carmen Sandiego on house arrest—her skin spray-tan orange with brown creases behind her knees and in the palms of her hands, arms covered in an anorexic down, silky scarves streaming behind her. In my memory they are always at the gas station, Lindsay and Samantha, arguing on the heels of a coke binge, in a car they’re about to drive in the wrong direction on the 110 freeway. Always in men’s hats.

In fact, if not feeling, it was not exactly like this. In old photos I see that Samantha wore a fedora most of the time, though they both would, together, and sometimes, when Sam wasn’t around, Lindsay would alone. Lindsay never wore a hat around Samantha if Samantha was not also wearing a hat. This made it seem like a prosthetic they passed back and forth, like a toy. There was precedent for this: Madonna wore the men’s hat like a strap-on. Marlene Dietrich, Katherine Hepburn, and other Hollywood stars of the 20th century retrospectively accused of lesbianism had more style. They were gentlemen in tails, the ringleaders of a gender circus where they themselves were the lions to tame, so they straddled the chair backwards in victory. In photos, their grin is the grin of a flasher, the smirk of a pervert, of a cannibal licking his fingers. Men had good reason to fear them.

On Samantha—and Lindsay, too—the hat wasn’t so scary. Hepburn, majestic, was a lion; Ronson snarled because she was just a cub. But the hat nevertheless made her comprehensible as a bad influence from the UK, since we already had Pete Doherty in soiled evening dress destroying Kate Moss. The hat was like a cold sore we got from the British sometime around 2005. We still have flare-ups: teetering away from dinner with her lawyers in stilettos, beating back the misdemeanors of her past, Lindsay still wears a fedora, stuck in the year everything went wrong for her.

Because culture is racist, a fedora on anyone “ethnic” signals dirty money and the shame of not knowing how to spend it well. Hats are for organized criminals, pimps and mafia dons, zoot-suiters and the Warren G. “Regulate” video. When Janet Jackson wears a fedora with a short yellow feather stitched into it, the fashion magazine calls it “Lady Mobster.” The fedora peaked, in popularity, with prohibition; on Lindsay it peaked with probation. Lindsay, not only white, was also the most disorganized criminal. She had not a single ally. The hat’s suggestion that there was a gang to which she could belong only called more attention to the loneliness of her brushes with the law.

Power, queerness, privilege, trash, camp, celebrity, anachronism, and crime—the expert coupling of showiness and shame: this is why the fedora belonged to Lindsay.

A brief interlude for hats in life:

One rainy morning in March, a tall man steps onto the train wearing, on his head, a stiff cherry-red fedora wrapped in clear plastic. His shirt is soaked through, beads of water tremble on the plastic around this magnificent, impervious hat, and it’s amazing—like he’s playing with the action figure still in the packaging. To me it confirms that the hat is no longer an accessory in the sense of a tool (say, for keeping a head dry) but an accessory in the sense of a co-conspirator: hats are everywhere producing bafflement, everywhere punking everyone.

The last Sunday of the month, the barista at the coffee shop is wearing a black felt and beribboned hat for which there is a name. An editor told it to me once, asking if this word was common parlance or just another example of the female writer’s tendency toward over-specificity. He said: Do you know what a “borsalino” is, without using Google? I didn’t. The barista in the borsalino is tall, limby, wearing plum-brown lipstick and adult braces. Taking orders, I can hear that she is either on her way in or out of an English accent. This seems key. On her, the hat works—she pulls it off. There is such thing as hat realness, in the drag sense.

On both of these strangers the absurdity of the hat has an underlying aggression I cannot place. It recalls the murderous dandyism of Malcolm McDowell in A Clockwork Orange. Freddy Kruger, too, wore a fedora.

Fedoras are “for men.” When a woman wears one, it’s meant to be an aberration. The winking transgression—however innocent or innocuous—that’s the whole point.

This seems somewhat defeated when we learn that the first fedora was a woman’s. It was named after the heroine of a 19th-century play—Fédora—who screwed up her love life while happening to wear a hat. Like the contemporary woman, Princess Fédora Romazoff is “passionate and self reliant.” As of the beginning of the play, she has had a disappointing love life, but trusts the man she is about to marry. Naturally, he cheats on her with another man’s wife. When this other man, Loris Japonoff, finds out, he kills Fédora’s fiancé and flees to France. Fédora decides to follow Loris, seduce him, and then kill him. Little does she know that Loris has actually saved her—“saved her from becoming the wife of a miscreant,” in the playwright’s words. This at least is the logic of Fédora. The details—moral, chronological—are ambiguous.

Princess Fédora falls for Loris, but “stifles her love” for the sake of manners, principles, and the rascal she’d hoped to marry. Even in a hat, a woman follows rules where a man does not. Loris addresses Fédora in cryptic doublespeak, suggesting, too subtly, that he has killed her fiancé because he loves her. Not the best reader, Fédora brings tragedy upon herself. She turns Loris in before he has a chance to confess his love. He’s dragged off by French cops; she kills herself “in expiation.”

Female celebrities possess a superhuman ability to set trends, and as Princess Fédora, Sarah Bernhardt—“the most famous actress in the world”—convinced French women to take up the fedora. One wonders if these women also took on some kind of curse. Fédora, the play, with its presumed history of failed loves, its conception of seduction as revenge, its miscommunications and missed connections, is a play about the horrors of dating. The fedora—on television, in the pages of the New York Times style section—is now a universal signifier of women’s romantic troubles. Perhaps it always has been.

Not so long ago the Times ran a story called “The End of Courtship?” Beneath it was a photo. “Denise Hewett says hanging out has replaced dating,” said the caption. Jennifer S. Altman for the New York Times had photographed Denise on a velvety mustard couch in a hotel lobby, wearing a tan fedora with a mustard ribbon for trim. The mustard ribbon matched the mustard couch matched the mustard highlights of Denise’s impeccable blowout. Denise was looking at her phone, texting with two hands, as if handling a Gameboy. She was waiting for her OKCupid date.

Hanna Rosin, corporate psychic, foreseer of the end of men, was brought in for expert opinion. “Many young men these days have no experience in formal dating and feel the need to be faintly ironic about the process,” she told the Times, “to ‘date’ in quotation marks”—because they are “worried that they might offend women by dating in an old-fashioned way.”

In other words, dating is like wearing a hat, available only through irony. Stylists and art directors know this. The image of a young woman wearing a hat signals to the reader: Manners have become so confused—this woman is wearing a hat! There are no mates for her. The fedora is not Monica Lewinsky’s sex-guerrilla beret made sweet with a bow, taking no prisoners with an infantile feminine twist. Nor is it Mary Tyler Moore throwing her beret to the sky—You’re gonna make it after all. We are not sure whether we’re going to make it, in a fedora.

But why a fedora? Princess Fédora does not deserve so much credit. One can only imagine that the women who wear fedoras are acting out a deeper cultural melancholia. Not sadness, but melancholia, in the sense Freud defined in Mourning and Melancholia, as a mechanism for dealing with loss. Without decent romantic prospects, the straight woman suffers an ungrieved loss. She has not lost any actual man—there are still plenty of those—but rather the fantasy of an ideal man, which her sisters have wisely told her is pointless to indulge. This fantasy has meant more than said partner, manifest, ever could, but now it’s a bad look; it’s another era’s out-of-fashion false consciousness, not to be worn. Denied the right to atavistically yearn for letters and sodas, the woman in the hat retains the fantasy of wanting a Perfect Man—a dominant man who will carry her across the threshold, call her on the phone and not text “sup” after eleven—by adopting his characteristics. By adopting his hat.

In order to preserve him, she must become him. This may or may not have been what Gloria Steinem had in mind when she said, “We are becoming the men we wanted to marry.” But the signal is complicated. This woman does not wear a fedora to say that she wants Don Draper. She wears a fedora to say, I want a man who is like a woman in a hat. That is, the best of both men and women; I want Feminist Ryan Gosling. She sustains the dime-store, midcentury masculine hero by taking on his dress as her own, but idealizes it all the more by feminizing it—since the problem with those men all along, the men in fedoras, was that they were nothing but money, manners, and chivalry. Their precise appeal rested on their chauvinism, a chauvinism that a woman today, wearing the hat and the pants, no longer accepts. This is where the hapless men who think they can trick women into finding them sexy or desirable by wearing a fedora make a serious misstep. Perceiving a vacuum in the market, this OKCupid subset acts the part of Lothario by posting fedora selfies with captions like “as a side note . . . I do own a toy collection to use on another for their delight.” This is the worst kind of man—fronting, opportunistic. The kind of man who picks you up at a funeral. Little do they realize: the funeral is their own.

Is the young woman in a fedora like princess Fédora, unhappy in love and yet naively hopeful for its future, seeking revenge—or is she like Lindsay, wearing a hat for confusion, fun, disguise, experiment? Is she drawn to the miscreant on OKCupid and incapable of seeing the truly loyal man whose principles keep him from rakishily, untowardly, taking what he wants for his own—or is she just trying on girls for a while? The woman in a hat does waste time on a detective game, in her Private Investigator outfit, hunting revenge for some past hurt and applying her interpretive skills to the wrong text. There is something tragic about her, and certainly about Lindsay. Stuck in the sun-in past of her child-star potential, when she was promised everything and it was all in front of her, she is an amnesiac, still paying old dues—going on dates, getting fired from bad movies. Lindsay still wears hats, but has gone on to date men. Men much worse for her than Samantha.

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