To that pocket-square-wearing, sidecar-sipping human known as the “Esquire man,” this was life as it was intended to be: a roomful of wags in natty suits throwing back cocktails and trading banter in one of Manhattan’s hottest restaurants, as willowy models and square-jawed movie stars circled the room.
At Esquire magazine’s “Mavericks of Style” dinner, held at Le Coucou on a rainy night this past November, spirits were so high, and consumed so freely, that it might as well have been 1966 — doubly so, since Gay Talese, Esquire’s living monument to the New Journalism of the 1960s, was holding court, dry gin martini in hand, a few yards away from Jay Fielden, Esquire’s new editor in chief.
“There was a period of time when Esquire had a real literary charisma, and there was a culture that responded to it,” said Mr. Fielden, 48, sounding nostalgic as he reclined in a banquette, wearing a steel-bluel Ferragamo suit and sporting what may be the best head of male hair in the magazine industry, a cascade of artfully coifed curls that calls to mind both the belletrist whimsy of Oscar Wilde and the gunslinger gusto of Wild Bill Hickok. “How do you make that urgent to a younger generation?”
It’s a question that may determine the fate of a magazine that for 84 years has not just sought to serve the American man, but to define him. Since the days of Hemingway, Esquire has provided a running seminar in the arts of manhood. It is where young men turned to learn to mix a French 75, tie a full Windsor knot, ogle (in purely aesthetic terms, of course) the latest lingerie-clad Hollywood ingénue and absorb life lessons from stoical, stubble-face cover subjects like Clint Eastwood and Bradley Cooper.
But times have changed. As we move into the era of transgender bathrooms and L.G.B.T.Q.I.A. studies, when millennials are more likely to take their cultural cues from Justin Bieber’s Instagram feed than 6,000-word profiles of Sean Penn, Mr. Fielden is charged not just with bringing back Esquire’s glory days, but with also figuring out exactly what the Esquire man — that is, the American man — is in 2017.
It is up to the 13th editor in Esquire’s history to decide if this is a crisis or an opportunity.
The New Esquire Man
“It felt like Armageddon,” Mr. Fielden said, recalling the fire that ripped through his modernist Connecticut home in 2010. “It just sent this noxious smoke throughout the house. You close your eyes. You can’t breathe.”
Seated in a glassy Esquire conference room on the 21st floor of the Hearst Tower in Midtown Manhattan, Mr. Fielden described how the fire and smoke, which was like “exploding 50 cans of spray paint,” destroyed perhaps 80 percent of his family’s possessions.
“Your first response is, ‘All our stuff!’” he said. “But the point is, it was oddly freeing. Subliminally, we all do things to preserve the status quo. The major lesson that has helped me as an editor is to realize not to hang on to the things that would keep you from doing something dangerous.”
It is a nice metaphor. But even Mr. Fielden admits that it is no simple thing to decide what to keep and what to discard when you’re translating the magazine of Capote and Cheever to the Skrillex generation.
On that pale winter afternoon, Mr. Fielden, wearing a blue windowpane Cifonelli suit, was reviewing the 102 editorial pages of the March issue, all taped on a wall before him. That issue, complete with a redesign, is the first that fully shows his vision for the magazine. The cover subject is not a chiseled hunk in the mold of Ryan Gosling or George Clooney, but James Corden, the host of CBS’s “Late Late Show.”
After seeing a Carpool Karaoke segment featuring Mr. Corden, Rod Stewart and ASAP Rocky, Mr. Fielden began wondering if Mr. Corden was a good model for the new Esquire man. “He represents a lot of what I’m after,” he said, explaining that his version of Esquire “is aimed at a reader who’s an upstart, an iconoclast, an independent thinker, the most charming guy in the room.”
A portly Everyman with an impish wit, Mr. Corden is at heart a disrupter, Mr. Fielden said, the kind of man who looks totally at home in a red custom-made Gucci suit and silk Gucci loafers embroidered with tigers, as he appears in the issue.
“I mean, here’s this bloke from England who’s a little overweight, with his zaftig charisma showing up, taking the latest slot that potheads and college students watch, and suddenly he’s become a viral sensation that’s global,” Mr. Fielden said, a trace of his Texas twang poking through.
That talk show host was hardly the only peacock to grace the pages of that issue.
In a telling sign that Mr. Fielden plans to blow out fashion coverage, adding color and spectacle, the March issue features a model wearing a “cyberpunk meets Outward Bound” foul-weather ensemble by Prada, including pink scuba sneakers and a raincoat with a print inspired by Google Earth, that might give Jared Leto pause.
“There’s no cigar smoke wafting through the pages,” Mr. Fielden said, “and the obligatory three B’s are gone, too — brown liquor, boxing and bullfighting.”
As a straight white man, Mr. Fielden does not exactly represent a departure for the top of the Esquire masthead. Indeed, his profile is almost too perfect for the job. Craggily handsome in a vaguely Willem Dafoe way, he grew up in San Antonio with a father who enjoyed hunting and fly fishing, so he has the “arts of manhood” element deep in his DNA.
But Mr. Fielden is also fashion fluent (he edited Men’s Vogue, working with Anna Wintour, until that magazine closed in the great magazine die-off of 2008 and 2009), as well as literary (he edited articles by the likes of George Plimpton at his first magazine stop, The New Yorker).
His ability to cross boundaries was on display at Town & Country, a magazine associated with ladies who lunch, where Mr. Fielden managed to increase revenues 46 percent over his five-year reign there, in part by attracting more male readers.
“I gave Town & Country some teeth, reporting on behavior that wasn’t always that which, well, Emily Post would approve, like having an evening toke instead of a Scotch on the rocks,” said Mr. Fielden, who still serves as that magazine’s editorial director.
While he aims to do the inverse at Esquire, and bring in more female readers, Mr. Fielden nevertheless has a legacy to protect at Esquire. Esquire, after all, has been the industry’s most exclusive boys club for eight decades running.
A Magazine Built on Myths
When Esquire debuted from its Chicago headquarters in 1933, it was a magazine with a mandate.
“Esquire aims to be the common denominator of masculine interests,” a mission statement in that first issue read. Esquire, the statement said, would be a pointed rebuke to the “mad scramble” for female readers (and their advertising dollars) by the general-interest magazines of the day, which provided features for men only “after the manner in which scraps are tossed to the patient dog beneath the table.”
Esquire provided anything but scraps. That first issue was like the publishing equivalent of “Meet the Beatles,” with Arnold Gingrich, the founding editor, serving up articles by a future Nobel Prize winner (Ernest Hemingway), a future poet laureate of the United States (Joseph Auslander) and a heavyweight champion (Gene Tunney), not to mention work by literary lions including Ring Lardner Jr., Dashiell Hammett and John Dos Passos.
Through the Depression and the war years, the pages of Esquire were the place to be for the brightest and brawniest of American writers. Hemingway published his classic story “The Snows of Kilimanjaro” in the magazine in 1936. F. Scott Fitzgerald seemed to spend more time in Esquire than in the Commodore Hotel bar, publishing 43 stories in the magazine in just seven years before his death in 1940 at age 44.
Despite its literary bona fides, Esquire was no undergraduate seminar. Thanks to steamy pinup illustrations by artists including Alberto Vargas, Esquire was basically Playboy before Playboy. A ban of Esquire by the Office of the Postmaster General led to a watershed 1946 Supreme Court decision on censorship that helped open the floodgates for Hugh Hefner’s topless Playmates the next decade.
Observers might have expected this monument to bourbon-and-shotguns manhood to crumble when faced with the rise of feminism, flower power and civil rights in 1960s. Instead, Esquire entered a second golden age.
“A successful magazine has to build a myth its readers can believe in,” decreed the celebrated editor Harold Hayes, and under his watch, Esquire did not just cover the ’60s, it became part of the story.
The art director George Lois, known for his cover showing Andy Warhol being sucked into a can of Campbell’s soup, turned the Esquire cover into a form of pop art: the boxer Sonny Liston as “the first black Santa Claus”; the Italian actress Virna Lisi with a face full of shaving cream for a 1965 article on “The Masculinization of the American Woman.”
Showing off his instincts for journalistic anarchy, Mr. Hayes dispatched the literary pranksters Terry Southern, Jean Genet and William Burroughs into the tinderbox of the 1968 Democratic Convention in Chicago. Facing down the armies of the police in the riot-torn city, the kimono-clad Mr. Genet, a prostitute and thief turned novelist, concluded that America would be better off being “reduced to powder.”
Like that heady spirit of revolution, however, Esquire’s zenith could not last. But as a result, for nearly 50 years, every new Esquire editor — there were six in the 1970s alone — assumed the job with an implicit mandate, to bring it back to its glory years.
There were game attempts. Clay Felker, the founding editor of New York Magazine, took over the publication in 1977 and attempted to revive it as Esquire Fortnightly. While Mr. Felker had his hits (movies like “Urban Cowboy” and “Legends of the Fall” grew out of articles on his watch), the magazine bled money and was soon bought by an upstart publisher of giveaway magazines headed by two young Tennesseeans, Phillip Moffitt and Christopher Whittle, who installed Mr. Moffitt, then 32, as editor.
Industry skeptics reacted as if Tiger Beat had snapped up The New Yorker, but the new regime rode the “hip to be square” 1980s, when classic Eisenhower-era suits, cocktails and social climbing roared back into fashion, to a striking turnaround, selling the magazine to Hearst in 1987.
But by 1994, Esquire’s rival, GQ, had surpassed it in circulation and advertising pages, with titles like Details making a claim on Generation X. Esquire replaced the highly regarded editor Terry McDonell with the longtime New York magazine boss Edward Kosner, who vowed to revive its legacy as a writer’s magazine.
Sometimes it worked. Other times, attempts to channel the spirit of Mr. Hayes fell flat, such as when Norman Mailer, then 71, took on the Madonna phenomenon. Writing in the third person, Mr. Mailer caught up with the star after a draining photo shoot, writing, “Of course her breasts would be the first part of her to express such physical discontent, even as any good fellow’s penis would shrivel when low in spirit.”
By 1996, The New York Times was observing Esquire’s “thinning spine and declining circulation.” A year later, Hearst handed the reins to David Granger, GQ’s celebrated executive editor.
Mr. Granger’s attempts to provoke did not always hit the mark. The endlessly dissected 1997 cover story “Kevin Spacey Has a Secret,” written with grand New Journalism pretensions, was widely viewed as a clumsy attempt to “out” Mr. Spacey, who compared the article to McCarthyism.
Even so, Mr. Granger settled into a 19-year-tenure — the longest in Esquire’s history — in which the magazine enjoyed a financial recovery, and became the Meryl Streep of the National Magazine Awards (it won 17 during Mr. Granger’s reign).
On Jan. 29, 2016, David Carey, the Hearst president, strode into the Esquire offices with Mr. Fielden to introduce him as the new boss.
To borrow Mr. Hayes’s phrase, it was time to build some new myths.
Manhood in the Trump Age
Mr. Fielden takes the helm at a time when men’s magazines as a category seem to be having an identity crisis. Details has shuttered, Maxim has cycled through editors, and Playboy has done away with its raison d’être, naked women.
It is easy to blame the internet, but to Mr. Fielden, that is a tired excuse.
“There are a lot of false narratives out there,” he said. “You tell me about the last time you had an amazing experience on a website that you wanted to print and hang on your wall? If that’s the Holy Grail, that’s something we’ve done with newspapers and magazines for our entire existence, and that’s where this thing has to hit, because the human race is not getting stupider.”
Even so, Esquire is pouring new resources into the web. This past December, Esquire’s 48-hour pop-up channel, “The Esquire Guide to Grooming” on Snapchat’s Discover platform, reached more than three million unique viewers. Hearst recently hired Steve Kandell, the former executive editor for features at BuzzFeed, to direct Esquire.com, a site that has received a traffic boost of 20 percent in the past six months.
The site managed to insert itself into the cultural conversation at numerous points during the recent election cycle, such as with an online-only reboot of the seminal ’80s satirical magazine Spy, or Peter J. Boyer’s bite-size scoop that Donald J. Trump was considering evicting the press corps from the White House, which became the talk of the Sunday-morning political shows.
This is not to say that an Esquire editor who reads the literary critic Christopher Ricks for fun in airports has any plans to scuttle Esquire’s prized long-form literary tradition to fit Twitter attention spans. Vicky Ward’s feature article in August, “Jared Kushner’s Second Act,” a prescient look at the political rise of Mr. Trump’s 36-year-old son-in-law, was just one of the 6,000-word-plus features under Mr. Fielden to create buzz within the industry.
“Bad short pieces read long, and good long pieces read short,” Mr. Fielden said. “I don’t think shrinking is necessarily bad. I’m a great fan of the haiku.”
If Mr. Fielden’s only challenge were competing with the internet, that would at least be a familiar problem. More confounding is the rapidly changing cultural landscape.
In the year since Mr. Fielden took over Esquire, the country has entered what seems like a full-fledged culture war. With so-called alt-right provocateurs like Stephen K. Bannon marching into power, and armies of women in bright pink hats marching in protest, it’s a little hard to say where the literate centrist coastal male with a taste for Raymond Carver — that is, the traditional Esquire man — fits in.
“I understand what the hurdles are, what the difficulties are,” Mr. Fielden said. “They’re certainly things that keep me up, and sometimes ruin my weekend.”
But, he added: “I look back on what the New Journalism invented, what Gay did, what Tom Wolfe did, what Norman Mailer did. They had to up the literary horsepower with new tools and techniques in order to compete with the speed and seismic shock of one insane event after another in the ’60s and ’70s. We’re just having to do the same thing.”