Gary Shteyngart liked the stick. It was a handsome, polished staff called a shillelagh, used in Ireland for walking and the occasional cudgeling. This one was on sale at the Armoury, a high-end men’s clothing shop in TriBeCa that could double as an Ivy League library.
“I’m in love with this thing,” he said of the shillelagh, which was made by Fox Umbrellas of London. President John F. Kennedy, who came to embody Ivy cool, had been a Fox enthusiast. Now, so was Mr. Shteyngart, the bespectacled 53-year-old Russian American novelist. “This might be my new way of living,” he said.
Having recently turned into an unlikely men’s style icon with a penchant for crisp martinis, tailored suits and vintage watches, Mr. Shteyngart could credibly entertain the purchase of a $250 stick, even if doing so might make him look like one of the insecure, status-obsessed Manhattanites who populate his novels. The most recent of those, “Vera, or Faith,” about a precocious Korean American girl growing up in a privileged Manhattan household while the nation descends into an all-too-familiar mix of extremism and indifference, is out now.
Mr. Shteyngart had been working on another novel — long and complex, involving spies — when David Ebershoff, Mr. Shteyngart’s longtime editor at Random House, invited him to lunch at the restaurant Blue Ribbon in Midtown Manhattan in the fall of 2023. Mr. Ebershoff broke some bad news: Mr. Shteyngart’s epic was not working.
Mr. Shteyngart, who had been having his own doubts, sat silently for a few moments. “And then he put his finger up in the air and said, ‘I have another idea,’” Mr. Ebershoff recalled. That idea — his new novel, coalesced into a manuscript in just 51 days. “I’ve never seen anything like it,” the editor said, praising the author’s “new level of emotional openness.”
Mr. Shteyngart’s sartorial tastes have also deepened. “I used to be so against dressing up,” he said, as Daniel Greenwood, the Armoury’s director for U.S. sales, outfitted him in an ocean blue City Hunter jacket, made in Hong Kong from Irish linen and selling for $1,000. Born and raised in chilly Leningrad (now St. Petersburg), Mr. Shteyngart had transformed into a Mediterranean flâneur, ready to face a New York City afternoon in late spring.
“It’s not surprising that someone so intellectual would gravitate toward a look that symbolized the intellectual class for much of the 20th century,” said Derek Guy, the men’s wear influencer, when asked about Mr. Shteyngart’s style.
Previously, his wardrobe “didn’t fit me,” Mr. Shteyngart confessed. A professor of creative writing at Columbia, he recalled showing up for an evening with the university’s president dressed in “I don’t know, a diaper.”
But there was no sign of diapers now. At his Gramercy Park apartment, Mr. Shteyngart changed into a $10,000 suit made for him out of six-ply Italian milled wool by the Japanese tailor Yuhei Yamamoto. Because he wrote about the suit for The Atlantic, Mr. Shteyngart was able to keep Mr. Yamamoto’s bespoke creation.
“Gary’s approach to clothing increasingly resembles his approach to watch collecting: taking pleasure in not only how things look, but how they’re made, why they’re made that way, who made them,” Mr. Greenwood said, comparing Mr. Shteyngart’s style to that of literary giants like Norman Mailer and George Plimpton.
Writers do not occupy the role in society they once did when Mr. Mailer held court at New York’s popular literary and celebrity hangout Elaine’s. Attention spans vanished. So did advances. Mr. Shteyngart recalled a “many martini lunch” with the Random House editor Daniel Menaker. “You’re one of the last people that’s going to make any money off this,” Mr. Menaker predicted.
Mr. Shteyngart’s lifestyle is thus all the more remarkable, hewing less to today’s dire realities than to the sunnier days described by the editor Graydon Carter and the mogul Barry Diller in their recent memoirs. His journey has also taken him — in a trajectory pioneered by the nation’s current president — from Queens to Manhattan. In 2010, he bought an apartment in a building off Third Avenue, which led The New York Observer to declare: “Writer Gary Shteyngart Goes Yuppie.”
Mr. Shteyngart started collecting high-end timepieces about a decade ago. On a coffee table in his apartment, where he lives with his wife, Esther Won, an attorney, and their 11-year-old son, Mr. Shteyngart laid out his 30 or so watches, which he keeps in a safe.
It was hard to ignore the Patek Philippe Aquanaut, which can sell for more than $100,000. He seemed drawn to an understated Universal Genève, once owned by an Italian railway worker. “Keeps terrible time, but absolutely beautiful,” Mr. Shteyngart judged with parental affection. Then there was an exquisite piece from A. Lange & Söhne. “There’s a group of people working in Germany to make these, and each one of them can recognize their own handiwork, because each one is slightly different,” Mr. Shteyngart said reverently.
Such craft work is “the opposite of A.I.,” he said, a rebuke to algorithmic conformity and incoherent techno-slop. “They combine taste, they combine history, they combine art.”
‘Living well is the revenge tour’
It was during the coronavirus pandemic that Mr. Shteyngart took a turn from schlubby to bespoke, from Brooklyn plaid to Milanese silk. And the change was precipitated by an unlikely source: his penis. Born in the Soviet Union, where the authorities discouraged religious practice, Mr. Shteyngart had not been circumcised at birth according to Jewish custom. The procedure, which occurred in Brooklyn at the age of 7, was not performed quite properly, leaving too much foreskin on the underside of Mr. Shteyngart’s maimed manhood.
Fast forward to the summer of 2020, when “a tiny hair” wrapped into a “tourniquet” around that excess foreskin “in the shape of a gift bow,” as Mr. Shteyngart wrote in The New Yorker. The knot “could not be prized loose using tweezers, and any attempts to dislodge it with my fingers only tightened it around the string of superfluous skin,” he wrote. It would not loosen, and his foreskin began “releasing what looked like a stream of pus.”
A series of medical interventions made the pain unbearable. Mr. Shteyngart said he contemplated suicide. Things got better after his wife’s college classmate, a plastic surgeon on the Upper East Side, showed him “how to tend to the tiny wounds that collected lint, bandage material and dead skin.” The healing accelerated after a doctor on Long Island prescribed an analgesic cream that included the antidepressant amitriptyline. Finally, Mr. Shteyngart’s long Russian winter gave way to spring.
“Living well is the revenge tour that I’ve done after the penis healed,” Mr. Shteyngart said, using a stronger word for his anatomy.
As Mr. Shteyngart was recovering, two novelist friends from upstate New York (Mr. Shteyngart also has a house in Dutchess County) died from cancer: Paul La Farge, at 52, and Rebecca Godfrey, at 54. Yet Mr. Shteyngart refused to brood in the expected manner of a Russian novelist. “I’m just like: ‘I’m going to be dead soon. Let’s do this right,’” he said.
Doing it right means strolling out of his apartment for a negroni in the resplendent confines of the National Arts Club. Then it’s on to Borgo, where a martini cart arrives almost as soon as we sit down.
Cannelloni arrived. Sausage. The sommelier poured orange wine from Virginia. Then more food, more wine. “I’ve always loved good stuff, because I grew up with so little,” Mr. Shteyngart said. His 2014 memoir, “Little Failure,” is a chronicle of ill-fitting clothes and disapproving parents who seem convinced that he is not going to meet their traditional immigrant expectations. His father hits him at home. At school, bullies await.
Mr. Shteyngart was accepted into Stuyvesant High School in New York in 1987. From there, he went to Oberlin College in Ohio, which is consistently derided in his novels: In “Vera, or Faith,” it is the College of Fading Repute.
Much as Mr. Shteyngart likes to poke Oberlin, he credits the writing professor Diane Vreuls with steering him toward writing. Given his “propensity for recreation,” Mr. Shteyngart believes he could have easily become a burned-out attorney at some Midtown firm. “The pot of Oberlin would have been replaced with Harvard Law wines and lines of coke,” he mused. “I would have been dead by now.”
After graduating in 1995, Mr. Shteyngart worked for the New York Association for New Americans, a resettlement agency in Lower Manhattan, spending most of his time writing “The Russian Debutante’s Handbook,” which Riverhead Books published in 2002 to widespread acclaim. Today, he refers to his debut by using only the title’s last word, but he replaces the second half of the word so that it becomes slang for a sexual act.
His next two novels, “Absurdistan” and “Super Sad True Love Story,” continued the trend of glowing reviews and strong sales. His was an America lonely and oversexed, information rich but knowledge poor. Mr. Shteyngart’s writing can be frenetic and over the top, but he has eclipsed many of the supposedly more serious novelists who came of age when he did. That may have to do with a sensibility adeptly attuned to our ever-edgy times. “I lean anxious, which overlaps with funny,” Mr. Shteyngart said. “This is why I keep surviving as a writer — my anxiety went into humor.”
His penis “thing”— again using stronger language — “put things into the stratosphere,” he said. “I realized I love people. I loved so much of life.”
Mr. Shteyngart became angry but also reflective. He had firmly moved into middle age, while he felt the United States was sliding into some version of the Soviet Union his family had escaped. In 2021, he published “Our Country Friends,” about a group of friends weathering the coronavirus lockdown in a converted upstate bungalow colony. The novel was more meditative than its predecessors; this newspaper called it “his finest yet.”
Manhattan, though still a source of pleasure (martinis, Irish sticks), is no longer inspiration. “It sucks,” he said of the city’s transformation into an Instagram backdrop. To write, he retreats to the country.
Mr. Shteyngart spends about half the year in his house upstate. The property sits on seven lush acres; the house itself is a Depression-era Craftsman and a showcase of expert woodwork. He enjoys being there. “I’m trying to make a really good life out of what we have,” he said.
As he recovered from the mangling of his manhood, Mr. Shteyngart became close with the author Salman Rushdie, who was seriously injured by a knife-wielding attacker in 2022. Reached by phone in mid-June, Mr. Rushdie compared Mr. Shteyngart to the great Russian novelist Vladimir Nabokov. “He’s up there, and he’s getting further up there with every book,” he said.
In an era when the charge of cultural appropriation still carries professional risk (though perhaps not quite as much risk as five years ago), Mr. Shteyngart’s decision to write in the voice of a tween Korean American girl was a bold one. He said he was partly motivated by his own son’s experience. “He and his little friends, they mention Trump all the time,” he said. “And when you’re growing up and you have to think about the Great Leader all the time, that’s always going to stick with you.”
As for his longstanding interest in Korean culture, Mr. Shteyngart traces it back to his time at Stuyvesant, where the student body was overwhelmingly Asian. His mentor Chang-rae Lee, the acclaimed novelist, is also Korean American, as is his wife.
As the sun set over the Hudson River Valley, Mr. Shteyngart poured a couple of glasses of scotch, watching fog roll over the countryside.
“This is my heaven,” he said. Not that he is entirely free of his trademark anxiety, even up here. “There was a very ominous-looking car that pulled up a couple of days ago,” he recalled. “I wanted to take a photo of it, just send it quickly to Esther in case I died.” But, once again, Gary Shteyngart survived.
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