Are the Hamptons Still Hip?

For years, the Hamptons were a hot summer destination for young, up-and-coming New Yorkers and the old and new moneyed alike. It was a place to see and be seen. Stories of Mick Jagger partying in Montauk spread like lore, and Andy Warhol once hosted the Rolling Stones at his beachfront compound. It wasn’t uncommon for young college graduates in the city to save up and pool together to rent a summer house and get a taste of the glamour.

In a 1999 interview with New York Magazine, Jay-Z put it simply: “I mean, the Hamptons is cool.”

The Hamptons still have a mythological reputation, fueled by the celebrity cachet that comes with square footage, seclusion and ocean waves. “Kaia Gerber, Ina Garten and Diplo walk into a bar — that is to say, the Hamptons holds a certain, je ne sais quoi? Where else would these mega names be in the same sentence?” said Jacob Rutledge, a 22-year-old model and content creator.

But the Hamptons are not what they once were. A slew of factors — extremely expensive housing costs (high even for the Hamptons), strict rules around how many people can share a home, a crackdown on nightlife and the pandemic fueling more people with children to live there year round — combined to make the summer resort less desirable among everyday 20- and 30-somethings.

Despite his instinct to marvel at the Long Island refuge, Mr. Rutledge, who lives in Ridgewood, Queens, isn’t going out to the Hamptons this summer. Instead, he’ll be close by at Fire Island.

“There’s a certain air when you take the boat to Fire Island, like a school bus taking these gay men to an amusement park,” said Mr. Rutledge. “The culture that Fire Island provides will always be the reason it stays in style. When I’m 50 plus, find me in the Hamptons.”

Even Gen Z’s favorite 80-something icon and recent Sports Illustrated swimsuit issue cover star, Martha Stewart, has divested, selling her East Hampton estate in 2021 for $16.5 million.

How Did the Hamptons Become the Hamptons?

The hipness of the Hamptons has always been cyclical, defined by whoever was trying to take control of it next — going from bohemian cool, upscale art world cool and eventually to glamour and glitterati cool.

Over the decades, new groups of people would come to the Hamptons and try to make the resort theirs, warping and grooming them to fit their own unique needs and desires. “The continuity in the Hamptons is that really wealthy people are looking to find something new to conquer,” said Corey Dolgon, the author of “The End of the Hamptons” and a professor of sociology at Stonehill College.

Sometime after the existence of Pangea but before Gwyneth Paltrow bought a place there, the Hamptons formed as a region on the southeastern end of Long Island, surrounded by the Atlantic Ocean — as in, there’s a lot of desirable waterfront real estate.

Before European colonizers arrived in the 1600s, Native Americans, including the Shinnecock and Montauk tribes, occupied much of Eastern Long Island. The outsiders co-opted Indigenous values and culture, enforced a money economy and introduced a patriarchal system of governance, Mr. Dolgon said. Clashes over land use between the newcomers and Indigenous people continue today. Wealthy residents and local officials have objected to the Shinnecock people’s construction of highway billboards and plans to open a casino on its reservation — both attempts to dampen the high poverty rate they face.

Centuries later, another early wave of outsiders — artists and writers — descended on the land. In the late 1800s, Walt Whitman published several works on his fascination with the natural wonder of the Hamptons. In an article in The Brooklyn Standard, he wrote, “To a mineralogist, I fancy Montauk Point must be a perpetual feast. Even to my unscientific eyes there were innumerable wonders and beauties all along the shore, and edges of the cliffs.”

Such descriptions “encouraged people — especially the Bohemian, artist types and young people with money — to go out to this unspoiled land,” Mr. Dolgon said.

The migration of artists then began to entice the wealthy to build summer cottages there, Mr. Dolgon said.

In the post World War II era, the Hamptons drew a new group of artists. With a loan from Peggy Guggenheim, in 1945 Lee Krasner and Jackson Pollock bought a home in the East Hampton hamlet of Springs for $5,000.

The postwar economic boom, along with the construction of the urban planner Robert Moses’ highways along Long Island, allowed for people of means to go out to the Hamptons more frequently and for shorter stretches of time, Mr. Dolgon pointed out.

The reputation of the Hamptons as a weekend getaway and summer vacation spot continued to grow, and by the 1990s and 2000s, “everybody wants a piece of the Hamptons,” Mr. Dolgon said. The dot-com boom and the rise of telecommuting led to “a new wave of money trying to put their imprimatur on the land.”

This is when the Hamptons become fashionable in an aspirational sense, and college graduates would save up to rent summer homes together. “For people who are up and coming,” Mr. Dolgon said, “they have to have a place in the Hamptons.”

In 1998, Diddy threw the first of his strictly all-white-dress-code parties at his East Hampton home, which Paris Hilton called “iconic.” The next year, Ivana Trump and Busta Rhymes sat together at Jay-Z’s Fourth of July soiree. One tabloid story that epitomized the craze at the time was of Lizzie Grubman, a publicist who New York Magazine crowned the “reigning queen of New York nightlife.” In 2001, after a fight with a bouncer outside of a club in Southampton, Ms. Grubman backed her Mercedes into a crowd of partygoers. It would become known as the “Summer of Lizzie.”

So, Then What Happened?

Now, it’s more likely to be coined the summer of sleepiness.

Last summer, when Ms. Paltrow’s daughter, Apple Martin, threw a bash at their Amagansett estate, cops reportedly shut it down. But Ms. Paltrow’s Cartier-sponsored pajama party, where “sleep milk” was handed out as a party favor, didn’t ruffle any feathers.

Decades back, towns began rolling out rules that would regulate the revelry. In 1975, East Hampton adopted legislation that barred groups of more than four unrelated people from living together in houses. Southampton has restrictions specifically on the number of people that can occupy bedrooms.

For a while, many looked the other way as friends, lovers and strangers split the cost of a summer house more than a dozen ways — sharing rooms, mattresses and more. In an episode of “Sex and the City,” Samantha Jones tells her friends about her 25-year-old assistant, who has “a summer share in Bridgehampton with 18 other girls. They have to sleep in shifts.”

Such a setup would be difficult to come by today, as residents began demanding stricter enforcement of the longtime laws. “The long tradition of dozens of young people crowding into a Hamptons house for a summer of wild abandon is under attack,” The Times reported in 2003, following several police raids, neighbors spying on each other and Southampton imposing tougher penalties for violators.

In a clampdown reminiscent of “Footloose,” even dancing can be punishable.

Shagwong Tavern, an unfussy, old-school restaurant and bar in Montauk that dates back to the 1920s, was a haunt visited by John Lennon, Bianca Jagger and Andy Warhol. “Get Off of My Cloud” by The Rolling Stones blasted from the jukebox, and people shimmied shoulder to shoulder into the A.M.

Present day, a sign out front reads “piano player wanted must have knowledge of opening clams.” All walks of life have known that they can come together there through music.

“It’s for everybody — the fisherman, the Wall Street guy, the celebrity, the contractor,” said Jon Krasner, who bought the tavern in 2015.

Last year, a building inspector ruled that moving furniture to allow dancing meant that Shagwong was illegally operating as a nightclub, which is a special permitted use in the region.

“We’re not going to make money being the best filet mignon place in town. We’re a bar,” Mr. Krasner said. “If people want to listen to a band and dance, then hell yeah, that’s what a bar is for.”

Rumors of ‘Fancy People’

But who are the Hamptons for?

It’s a given these days that it takes money to enjoy the Hamptons. During the pandemic, many New Yorkers moved to the Hamptons full-time and the region’s D.N.A. changed — more businesses stayed open year round, and school enrollment went up. According to census data, the population of East Hampton rose by more than 30 percent from April 2010 to April 2021.

Prices went up even more. For the first quarter of 2023, the average sales price of a home reached a record-breaking $3.08 million, according to Douglas Elliman. Rentals aren’t cheap either. “For a relatively updated three-bedroom house with a pool, you’re looking at like $1,000 a night,” said Joseph Van Asco, a broker. “The high end begins around $100,000 a month.”

“Housing is probably the number one driver of why the 20s and 30s are sort of retreating from the Hamptons,” said Britton Bistrian, an Amagansett-based land-use consultant. “A share house, back in the day in the ’80s and ’90s and even into the 2000s, was something that was attainable to a young professional. And I would say that it’s not anymore. They’ve been priced out just as much as working class people have been priced out.”

Demand is going down. There have been reports that summer rental prices are dropping, as there are more homes in the region than people willing to rent them. But that might not be enough to draw back trendy young folks.

The Hamptons represent a conspicuous wealth that isn’t as celebrated as it may have been in the 1990s and 2000s. The media we consume is largely dominated by eat-the-rich plotlines — think, “Triangle of Sadness,” “The Menu,” and “White Lotus.” So maybe it’s not unanticipated that young people would have little interest in conforming to the lifestyle of the Hamptons.

“I think of the Hamptons as a vacation spot for a certain subset of affluent New Yorkers who probably use ‘summer’ as a verb rather than a noun,” said Jade Song, a 26-year-old art director and the author of “Chlorine: A Novel.” She won’t be leaving New York this summer, but will still get her beach fix — “I will be eating vareniki, lagman and khachapuri at Brighton Beach,” Ms. Song said.

Sunny Hostin, 54, a co-host on ABC’s “The View” and an author, also used to feel that same way. When she was in her 20s, Ms. Hostin “had heard rumors of this place where fancy people visited.”

Even though she was intrigued, Ms. Hostin wasn’t in a rush to visit at first. “It didn’t have the reputation, in my view, as a haven for people of color,” she said. “While inviting, in my mind, because it was this glitzy, wealthy, rich place, I didn’t really gravitate toward it at first, because I didn’t know if it was a fit for me.”

But her opinion changed in her 30s, when she discovered the historically Black beach community known as SANS in Sag Harbor. She began renting a home there during the summer months, and it quickly became a tradition. “I have memories of clam digging in the bay, searching for crabs with my kids,” she said. “I have real history there now.”

Inspired by these experiences, Ms. Hostin wrote “Summer on Sag Harbor,” set in SANS. She hopes it can help change young people’s minds about the Hamptons. “I can’t believe I felt that way,” Ms. Hostin said. “They need to visit A.S.A.P., even if it’s just for a day — one day is all you need to know that you belong there.”