When Jay Fielden, late of Esquire, announced his departure as editor-in-chief this past May, he did it in foppish style. An Instagram post showed him leaving Hearst Tower dressed in a safari jacket and dark sunglasses, designer bags in hand. The photo, which fastidiously aped a famous shot of Jack Nicholson, was roundly mocked on social media. But it served as a fitting, if unwitting, symbol of how the Esquire of today stands in comparison with the Esquire of an earlier era—as a self-conscious echo, a superficial imitation of its former self. Nicholson, after all, was merely living his life; Fielden was playing pretend. The door, closing behind him, closed not only on a three-year run in which the magazine he helmed won not a single National Magazine Award—this after a 19-year span in which his immediate predecessor won 17—but also, it was felt in some quarters, on the cultural moment when such a thing as a men’s magazine had any remaining relevance.

Esquire, Details, Men’s Journal, Maxim, Playboy—it would be easier to list the men’s titles that haven’t shut down, cut issues, changed owners, blown up their editorial strategies, or become all but unrecognizable since 2015. In a tough media environment, men’s magazines are suffering more than most. Some—notably, Playboy and Esquire—appear to have decided that appealing primarily to men is no longer the best way forward. Their recent issues serve as signposts toward the future that, we are told over and over these days, is female—or, better yet, divorced from the gender binary altogether. What we stand to lose from their cultural eclipse is a certain ballast and guidance just as men need it most.

In 2017, more than twice as many men died of opioid overdoses in the United States as women—32,337 to 15,263. The national suicide rate stands at its highest level in 50 years, and while it has increased for both sexes, men are nearly four times as likely to take their own lives. More women than men now attend—and graduate from—four-year colleges. At the very moment that large numbers of American men are adrift, in the very midst of their hunger for meaning, men’s magazines are leaving them behind.

If a magazine for men now sounds as hopelessly passé as a private gentlemen’s club, Fielden himself helped to further this impression. When he moved to Esquire from Town & Country in 2016, one of his stated goals was to attract more female readers. “There’s no cigar smoke wafting through the pages,” he told the New York Times, managing to caricature a certain subset of men even while dismissing them, “and the obligatory three B’s are gone, too: brown liquor, boxing, and bullfighting.” The “Esquire man” would henceforth be more urbane and literary, less retrograde—altogether less specifically male.

Blessed with the important hair of the Men’s Vogue editor he once was, Fielden increased Esquire’s fashion coverage and sought to resurrect the “literary charisma” of its glory days. His final issue featured an oral history of the privileged coterie of enfants terrible—Bret Easton Ellis, Jonathan Lethem, Donna Tartt—that congealed at Bennington College in the 1980s. When news of his ouster broke, the Times lamented that “an editor with a fondness for literature and high fashion may no longer be the Esquire man.”

But this was hardly the point. During Fielden’s tenure, Esquire reached a crossroads, or perhaps an impasse. Men, it seemed, were on the way out. Each news cycle sent a new #MeToo scandal screaming across the sky, while the transgender movement was metastasizing from the liberal academy to the mass media, with yesterday’s radical absurdities quickly calcifying into today’s sacred truths. Fielden, with a teenage son of his own, faced a choice: either to mount in his magazine’s pages a full-throated defense of the virtues of masculinity or to knuckle under to the prevailing antimale sentiment.

He tried to do both—which is to say, neither. In his letters from the editor, he deplored the balkanization of American society and the “Kafkaesque thought-police nightmare” wrought by political correctness, while paying lip service to “sexual fluidity” and the #MeToo movement. Though clearly liberal, he was willing to break with consensus: he had doubts, for instance, about the Times’s anti-Trump zeal, its transformation into “something approaching a high-end HuffPo,” staffed with card-carrying members of the #Resistance. Even the fiction he published—fiction being an occasional presence these days in the periodical once graced by Saul Bellow and Milan Kundera—split the difference, with a story apiece by T. C. Boyle and by feminist author Lauren Groff, who spends her days, according to Twitter, being “bitterly disappointed in men” and “boiling over with redhot rage at the deep and evil roots of structural misogyny.”

Amid flagging sales, Fielden’s third way evidently failed to curry favor with the new president of Hearst Magazines, Troy Young. Having ascended to the top job from the company’s digital-media division in 2018, Young retains his loyalty to the medium that made him. Last fall, he handed the reins of another flagship Hearst property, Cosmopolitan, to Jessica Pels, who had edited the magazine’s website. Pels has since filled the print edition with practically subliterate articles on such consciousness-raising topics as the inequity of the “orgasm gap” between men and women.

By that standard, Esquire stayed remarkably sane, even as it dropped under Fielden from ten issues a year to eight. One landmark feature, published in March 2019, was “About a Boy”—a profile of a 17-year-old from the red part of Wisconsin named Ryan Morgan. It was, Fielden declared, a way “to look at our divided country through the eyes of one kid.” (He meant for it to be the first in a series of pieces on growing up today, with the inevitable black, female, and LGBTQ profiles to follow.)

What the piece revealed was a boy on the cusp of manhood—independent-minded, politically moderate, and mostly sure of himself, but deeply unsure about how to navigate the treacherous waters of today’s victim culture, especially when it came to the opposite sex. “I know what I can’t do,” he says at one point. “I just don’t know what I can do.” Reading the profile, I couldn’t help but recall a time when men’s magazines would have supplied not only the question but the answer.

Esquire was created to fill a void. In 1933, when it launched, magazines of supposedly general interest catered primarily to women because women were the primary audience sought by advertisers. The female of the species was overwhelmingly taken to be the “purchasing agent” of her family and, through the power of the purse, wielded considerable influence on mass media. As a 1929 advertisement in Printers’ Ink put it, “The proper study of mankind is man . . . but the proper study of markets is woman.” The key insight of Esquire’s founders was that if affluent urban men could be persuaded to become consumers in their own right, they might form a readership capable of sustaining a magazine that served their interests.

In its inaugural issue, Esquire declared that it was “only getting around at last to a job that should have been done a long time ago—that of giving the masculine reader a break.” Features aimed at men would not be included merely, as in other magazines, “after the manner in which scraps are tossed to the patient dog beneath the table.” Esquire’s first editor, Arnold Gingrich, who led the magazine until 1945, seems to have viewed the neglected men of America much as Jesus viewed Saint Peter when he said: “Upon this rock I will build my church.”

The resulting “Magazine for Men” was, according to scholar Kenon Breazeale, “the first thoroughgoing, conscious attempt to organize a consuming male audience.” The fashion illustrations printed in 1930s issues of Esquire, like those in the contemporaneous trade journal Apparel Arts (which would later be published by Esquire and eventually evolve into Gentleman’s Quarterly), are prized by aficionados to this day as representing the pinnacle of gentlemanly elegance. However rarefied the images seem today, however, the early Esquire was “very much targeted at a mass audience, even though the kind of reporting that you would have seen [in its pages] would have been pretty high-falutin’,” says Sean Crowley, a former menswear designer at Ralph Lauren who owns a vintage clothing store in Brooklyn. “The reporters and photographers would be at Royal Ascot, or in Biarritz or in Cannes. But it was really trying to inspire men—every man—to dress better and to take pleasure in dressing.”

And it wasn’t all clothes. From the start, Gingrich assembled a list of high-octane writers of real literary merit: the first issue alone boasted Ernest Hemingway, John Dos Passos, and Dashiell Hammett as contributors, as well as golfer Bobby Jones and boxer Gene Tunney. Esquire broke boundaries, too. In April 1934, Gingrich published the first of several short stories by Langston Hughes. Describing him as “a brilliant young Negro author,” the editor admonished readers who might have doubts that “there ought to be one magazine in America in which a man can read stories like this.” Readers agreed. What followed was a years-long relationship that included the first publication, in 1936, of Hughes’s searing poem “Let America Be America Again.” Crowley, who collects issues of Esquire from the Gingrich era, describes them as “total gems . . . absolutely jam-packed” with long-form journalism, fiction, and coverage of sports and current events.

Balancing the highbrow editorial matter were broad jokes, risqué cartoons, and “cheesecake”—illustrations of scantily clad women. One critic denounced the magazine as an “unholy combination of erudition and sex.” In 1943, the postmaster general revoked Esquire’s second-class mailing permit, deeming the periodical insufficiently edifying, and it took two years and a landmark Supreme Court decision for the privilege to be reinstated.

By the 1950s, however, Esquire had lost its edge; the time was ripe for a young upstart to reinvent its M.O. for a new generation. “From an editorial perspective, there was little revolutionary about Playboy when it entered the marketplace,” writes Elizabeth Fraterrigo in Playboy and the Making of the Good Life in Modern America. “The magazine borrowed heavily from the pathbreaking formula of Esquire in the 1930s, which promoted a vision of upscale, masculine consumption and heterosexual vitality as a welcome break from a female-oriented consumer society.”

Hugh Hefner’s “genius,” writes Fraterrigo, lay in recognizing how the postwar economic boom would allow Playboy to reach a much larger audience than the Depression-era Esquire ever could. By 1958, the oversexed younger brother of Esquire had overtaken its sibling’s circulation, and by 1960 it had achieved a paying readership of more than 1 million. But Esquire revived the following year under an idiosyncratic and indefatigable new editor, Harold Hayes, an avowed enemy of the ordinary who put heavyweight champion Sonny Liston (an ex-convict) on the cover in a Santa hat and wasn’t afraid to commission highbrow pieces from the likes of W. H. Auden. “His tenure at Esquire helped to kindle a renaissance in journalism,” Lee Eisenberg, a junior editor under Hayes who became the magazine’s editor-in-chief in 1987, later recalled. “It also touched a flame to a revolution in magazine design and art direction.” In the decade that followed, the two magazines—along with Gentleman’s Quarterly—flourished side by side.

If Playboy catered to men at their most prurient and self-gratifying, it also appealed to them at their most thoughtful and worldly, with fiction by Nabokov and Murakami and interviews with figures such as Miles Davis and Steve Jobs. Prurience aside, for more than 60 years Playboy held firm in the belief that being a heterosexual male was worth celebrating.

A look inside the Spring 2019 issue shows just how far Hefner’s brainchild has traveled from its original conception. Among its contents: a profile of anti-Trump comedienne Michelle Wolf; an antimale anti-poem, the premise of which is that the female author—“of mixed West Indian and West African heritage”—has to cut ties with a friend who sticks up for men too often; a brief profile of action star Frank Grillo that opens with him “holding a pink cocktail” and singing “It’s Raining Men,” accompanied by photos of him baring his abdominals in low-slung jeans; and, not least, self-portraits by “the first Muslim woman to appear nude in Playboy,” with a cheerleading introduction by photojournalist Lynsey Addario. Here is the less than statuesque photographer-model, Yumna Al-Arashi, in her own words: For “an Arab American, a Muslim and a woman in general, our bodies are often not our own. Having a female editor ask me to portray myself the way I wanted to be seen is really badass and history-making. . . . How do I want to talk to the male gaze for the first time?” Her photos, we are told, are “the complete opposite of sexual.”

All this is in keeping with the magazine’s new allegiance. Since the May/June 2018 issue, Playboy’s cover has declared it no longer “Entertainment for Men” but rather “Entertainment for All.” We seem to have gone back to the time when, as Gingrich wrote, female readership was “valued so highly as to make a step-child out of the interests of male readers.” No comparable shift is occurring at women’s magazines, which are still written, edited, and designed largely by and for women. That many aspects of the old Playboy can still be found in its pages only makes the foreign elements that much more jarring.

When it comes to Ryan’s question—“What can men do?”—the broader culture isn’t much help in answering. These days, women sometimes appear to view men as little more than a necessary, or perhaps an unnecessary, evil; as something to be shunned; as an obstacle to be leaped over or shoved aside.

Having succeeded in breaking open the old boys’ clubs, professional women have set about building exclusive clubs of their own. Witness the striking success of The Wing, a coworking space and social club for women that opened in New York’s startup-friendly Flatiron district in 2016. For a handsome price, members gain access to female-centric amenities such as lactation rooms and luxury beauty products, as well as private phone booths, a color-coded lending library, shared workspaces saturated in the pale shade known as “millennial pink,” and an in-house café. Fueled by over $100 million of venture capital, The Wing has since opened satellite locations in the trendy neighborhoods of Manhattan’s Soho and Brooklyn’s Dumbo, while expanding to Washington, D.C., Chicago, Los Angeles, San Francisco, Boston, and London.

New Yorkers who can’t afford The Wing—an all-city membership costs $2,700 a year, or $250 a month—can join The Camaraderie, a women-only club that aims to be “purely positive and uplifting.” There is no office space, but for $360 a year (or $35 a month), members enjoy monthly cocktail parties, brunches, professional workshops, yoga and spa days, a book club, and other curated experiences. (Motto: “Be strengthened. Be pampered. Be inspired.”) The justification for such clubs is that women need safe spaces, away from men, in order to thrive; that they succeed best when in the company of other women. Yet women have done well in coed environments: across all racial and ethnic groups, women are now more likely than men to have earned a bachelor’s degree by age 31, according to the Bureau of Labor Statistics.

In early 2018, the New York City Commission on Human Rights began investigating The Wing for its exclusion of men; several months later, a lawyer in D.C. brought a $12 million gender-discrimination lawsuit against the company. Yet antidiscrimination laws have hardly slowed the startup’s growth. In September 2018, both as a sop to critics and as an appeal to its “female-identified” and nonbinary members, The Wing adopted a new membership policy that evaluates applicants not on their gender but on their commitment to women’s advancement. The new policy is likely a fig leaf. As the D.C. lawyer, James Pietrangelo, who is representing himself as plaintiff, pointed out in a court filing last October, the new criterion is subjective: “The Wing retains absolute discretion to determine who is and is not ‘committed’ to The Wing’s ‘mission’—and thus [it] can easily be a proxy or cypher for excluding all men.” (The company’s website still describes it as a “community of women.” Its podcast and biannual magazine are called No Man’s Land.)

In media outlet after media outlet, one hears the notion that masculinity itself is a problem to be ripped out by the roots. “Science says toxic masculinity—more than alcohol—leads to sexual assault,” FiveThirtyEight recently told its 1 million Twitter followers. As Quillette editor-in-chief Claire Lehmann pointed out, what the studies in question actually found was that antisocial personality disorder and psychopathy are better predictors than alcohol use of sexual assault. The construct being measured was not “toxic masculinity.”

If there was a time when women were unfairly blamed for various social ills, the bugbears of our present age are overwhelmingly male: the leering desk-mate and predatory boss, the (mythical) campus rape crisis, the intractable wage gap, the patriarchy itself. Even men’s preference for office air conditioning has now been reported, by USA Today and the Washington Post, to be hurting women’s productivity. (Never mind that higher temperatures appear to make men less productive.)