Without Taavo Somer, the high priest of heritage chic in early 2000s New York, the Strokes generation may never have adopted Paul Bunyan as a style muse, decorated their apartments with cabinets of curiosities, or decided en masse that unkempt beards were suddenly cool for the first time since “Hotel California.”

In the shadow of a city recovering from the World Trade Center attacks, all the way through his Bloomberg-era heyday, Mr. Somer lorded over a tiny yet influential style empire in the Lower East Side.

At the back of Freemans Alley was his nouveau-retro restaurant, which became a clubhouse for downtown scenesters and fueled a craze for taxidermy.

At the mouth of the alley was Freemans Sporting Club, the home of his men’s wear label, which helped spark the “urban woodsman” look — flannel shirts, Red Wing boots, rolled selvedge jeans as coarse as sailcloth — that spread to the racks at J. Crew. A Prohibition-style barbershop featuring straight-razor shaves and handlebar mustaches became a widely copied formula.

Mr. Somer, in other words, made a career out of making the unlikely inevitable. Now, he’s betting he can get the cool crowd, now older, into golf.

“Is it a game or a sport?” Mr. Somer, 48, said on a sweltering Friday last month, peering down from a grassy hill at the meandering nine-hole golf course at Inness, his reimagining of a country club in the Hudson Valley town of Accord, N.Y.

The 220-acre resort features a clubhouse (actually a sleek farm-to-table restaurant with Scandinavian Brutalist furniture), a 12-room hotel in a rustic Colonial style, two saltwater swimming pools, two tennis courts and a rustic golf course designed by King Collins of Chattanooga, Tenn., which Mr. Somer described as the “bad boys of golf.”

But it is not a country club. “I’ve never felt comfortable hanging out with all the bankers at country clubs,” Mr. Somer said, dressed like a groundskeeper in grimy rolled jeans and a sweat-drenched black T-shirt and cap.

Mr. Somer, in fact, does not play golf. “I’ve never even touched a club,” he said.

“What I connect with is that it looks like a park,” he added. “Maybe this is naïve, but I think that one of the big draws for golfers to a golf course is the natural environment. I think it also happens with fishing or hunting, too. You can’t just go walk a park as a guy. You’ve to say, ‘Oh, look, I killed this deer, I hit this ball.’ You have to be productive.”

Therefore, he aims to be “a disrupter in the market, like Stumptown did with coffee.”

The In Crowd?

Inness offer memberships, which include priority tee times and hotel reservations, for $1,500 a year. But they are not required.

As with every Taavo scene, it is self-selecting. You know if you belong. You appreciate the Aesop hand wash in the hotel, the Astier de Villatte candles and Shoyeido incense in the greenhouse gift shop. You catch the reference to George Inness, the 19th-century painter influenced by the Hudson River School, or at least get why that is cool.

Over the course of a 20-year career as a tastemaker, Mr. Somer has relied on a simple form of market research: If he himself desires something, he trusts others will follow. They usually do.

And these days, there’s no shortage of New York creative types like Mr. Somer and his wife, Courtney, who (with their daughters Tessa, 10, and Isla, 8) hit a certain point in their lives and fled the pressures of the city for a quieter life upstate — an exodus many more city dwellers made during the pandemic.

Since moving full-time to the Hudson Valley five years ago, Mr. Somer and partners have opened Hotel Kinsley, a boutique hotel dotted with midcentury furniture in a stately bank building from the 1860s in nearby Kingston and a brick-oven pizzeria called Lola a few blocks away.

The inspiration for Inness, which he designed with Post Company, which created the Brooklyn-friendly Scribner’s Catskill Lodge in Hunter, N.Y., sprung from a backyard barbecue at Mr. Somer’s house five years ago.

“Before you know, there are 20 families hanging out, the kids are in the pool and there are pool towels building up, and I’m grilling and sweating,” Mr. Somer recalled. “I was like, ‘This would be so great if we were at a resort doing this, and they would clean up after us.’ So I thought, ‘I guess I’ll have to make that.’”

Inness, which was created with the New York developers Charles Blaichman of CBSK Ironstate and Lee Pollock and had its grounds designed by Miranda Brooks (who gave Anna Wintour’s property in the Long Island hamlet of Mastic its rugged, pastoral look), is a bet that the people who want the same things Mr. Somer wants have reached a critical mass.

“Freemans always felt like an escape from the city jungle because it was like one of these rustic restaurants in the countryside that are hundreds of years old,” said Olaf Breuning, 51, an artist who lives in Kerhonkson, N.Y., and became a charter member. “Now with Inness, Taavo is bringing the spirit of the city to the countryside. I can go up there once a week to see friends, talk about art or graphic design.”

That is certainly Mr. Somer’s intention. He hopes that Inness will eventually start to feel like a stylish update on a Catskills family resort from the 1960s. “You go there and you know people already,” he said. “You just kind of have your preset crew.”

Fortunately, Mr. Somer has been building a large one for more than two decades.

A Hidden Gem

It all started with a Halloween party.

In 2003, Mr. Somer, then 30, had recently moved to New York from Minneapolis, where he was an architect. By day he worked for the nightlife impresario Serge Becker. By night, he held saturnalian parties at a downtown strip called the Pussycat Lounge with his friend Carlos Quirarte.

Searching for a space for a big costume bash, Mr. Somer went to check out a former cafeteria for the Bowery Mission at the end of a dark alley off Rivington Street. Mr. Somer was smitten.

“It was like out of a Scorsese movie,” Mr. Somer said. “It was so New York, with all the fire escapes, and the steam coming out of the building. Instantly, I was like, ‘I just want to do something here.’”

He also sensed a need. “It was a depressing time in the city after 9/11, and everyone felt it,” Mr. Somer said. The scruffy young downtown types he hung out with were clamoring for their own generation’s version of a Mudd Club or Paradise Garage.

The result was Freemans, which he opened the following summer with a business partner, William Tigertt. In an era when Vegas-worthy megaclubs were at their zenith, Freemans offered a striking departure.

Drawing from the Revolutionary War-era Americana that Mr. Somer grew up with, as the only child of Estonian immigrants in Chadds Ford, Pa., he transformed the fluorescent-lit cafeteria into a design-forward reinterpretation of a Colonial hunting club.

The raw plank floors, the Edison bulbs, the taxidermy swans, deer heads and pheasants popping up on seemingly every surface — “the narrative was that this was a clandestine secret meeting place of the founding fathers,” Mr. Somer said.

“Freemans was a little escape hatch from the grid of Manhattan,” Mr. Becker said. “It was like one of those magical corners you find in a European town.”

The vibe was “hideaway,” but word quickly got out, as the likes of Uma Thurman, the Olsen twins, Maggie Gyllenhaal and members of Arcade Fire began patronizing. Jenna and Barbara Bush, the president’s daughters, were famously unable to secure a table one night in 2004.

This was an era when Malcolm Gladwell’s “The Tipping Point” was considered a must-read and Mr. Somer was a ready-made “maven” — Mr. Gladwell’s term for socially connected, in-the-know types whose curiosity and taste for the obscure sparks viral trends.

Everyone’s a Lumberjack

Taavo did taxidermy, and suddenly everyone downtown was doing taxidermy. Taavo did Freemans, known for its hidden, “speakeasy” feel, and suddenly speakeasies were everywhere.

Little wonder that scores of young men suddenly wanted to dress like Mr. Somer, too.

He was happy to oblige. With little clothing experience outside a line of T-shirts he and Mr. Quirarte sold at Barneys, Mr. Somer and Mr. Tigertt opened the Freemans Sporting Club shop in 2005. F.S.C., as it was known, showcased Mr. Somer’s rugged take on dandyish Savile Row suits, which he designed in collaboration with Martin Greenfield, the celebrated Brooklyn tailor, as well as his own streamlined updates on classic American brands like L.L. Bean and Orvis.

With its retro décor and time-machine barbershop (conceived by his friend Sam Buffa), F.S.C. felt like a portal to a mythic lost America where men still knew how to tie a full-Windsor knot, replace the carburetor on a Ford coupe and field dress a 10-point stag.

“Taavo’s genius was that he created stage sets for all these boys playing men to act out their visions of masculinity. He was like Hugh Hefner in Red Wing boots and a deadstock suit,” said Michael Hainey, a deputy editor for Graydon Carter’s newsletter, Air Mail, who was formerly at GQ.

“This whole generation,” Mr. Hainey added, “grew up in bland, empty, sexless exurbs where there was no grit or masculinity. It’s no surprise ‘heritage’ resonated with them. I think Taavo was more responsible for more of these guys sprouting wispy facial hair than puberty was.”

Mr. Somer did not invent heritage chic. Creative types were already rediscovering old-fashioned selvedge denim and classic outdoor wear by legacy brands like Woolrich and Filson. “It was a little like Nirvana’s ‘Nevermind,’” he said of his label. “There were other bands with similar influences doing grunge. Nirvana just distilled it.”

As lumberjack-chic became a uniform for trend-conscious men around the country, Mr. Somer was soon being hailed as the “patron saint of hipsters.”

“I remember I was at South by Southwest ten years ago and there were guys in stocking caps and flannel shirts as if it was 30 degrees out, and it was 105,” said David Coggins, a men’s style writer who collaborated on the 2016 art book “Freemans: Food And Drink, Interiors, Grooming, Style.” “I thought, ‘Taavo, damn you!’”

By the early 2010s, Mr. Somer, along with his various partners, had assembled a mini empire, adding cool canteens in the East Village and Williamsburg, along with a nautical-themed bar in the West Village called The Rusty Knot.

It would not last. Before long, his New York empire would begin to shrink, and would sell his men’s wear label to Japanese investors in 2016.

He did not necessarily want it to last. The grind of the 16-hour workdays were wearing on him. “In New York, it’s like you are lucky if you can be creative for three hours a week,” he said in a 2011 New York Times profile. “And then the other 100 hours you’re just slaving away.”

No More Taxidermy

As the sun descended over Inness that Saturday, Mr. Somer was taking in the golden-hour view of the grounds from a flax-colored armchair in the Inness lounge, discussing the Danish sensibility of its lime-wash walls and the utilitarian design of the building itself, which he described as a “a wormhole between an old 17th-century Dutch barn and a brand-new Swiss minimalist museum.”

Mr. Somer, who once dreamed of being a fine artist, sees every project as an installation of sorts, as well as a business, and wanted Inness to make its own statement, far removed from the retro funkiness of Freemans.

“I didn’t want to be the taxidermy guy,” he said, his dog Indy, a Brittany, nuzzling at his feet. “We could have done Freemans Vegas, Freemans L.A. and Freemans coloring books and probably made a lot more money. But I want to make things that reflect the place I’m in, and who I am, at that moment.”

The city, too, has evolved, but he no longer mourns the glassy towers rising in place of dive bars and clubs on the Lower East Side.

“I mean, I know people talk about the price of all the condos and all that,” he said “But it’s not like I think that the city has really changed or gotten boring.”

“Maybe,” he added with a smile, “it’s that I got boring.”

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