As anyone with a passing familiarity with New York City has known since time immemorial, Manhattan’s Upper East Side is many desirable things — safe, centrally located, filled with museums, lined with stunning pre-war apartment buildings and townhouses — but it isn’t cool. It’s the city’s most conservative, buttoned-down neighborhood. Even its counterparts in other cities, like Washington, D.C.’s Georgetown, are blessed with hipper restaurants and clothing boutiques. The reason is the neighborhood’s very strength: During the middle of the 20th century, when middle-class and wealthy white people fled from central cities in droves, the Upper East Side hung on. The result is that while previously crime-ridden or abandoned parts of Manhattan’s Downtown and West Side went through a bohemian gentrification phase on their way to fancy, the Upper East Side and its southern neighbors like Murray Hill and Gramercy Park stayed solidly bourgeois.

So a fresh irony has been discovered by the New York media: As recently gritty downtown and outer-borough neighborhoods that used to frighten white-collar immigrants from suburbia have emerged as the new capitals of cool, their housing prices have zoomed past the Upper East Side’s less desirable edges. Now, report publications such The New York Times and the New York Observer, young people who would have wrinkled their noses at the city’s squarest neighborhood are moving there, and bringing their hipness with them.

On Wednesday, The Daily Beast even went so far as to endeavor to explain “Why the Upper East Side Is Now Cooler Than Brooklyn.” Writer Tom Teodorczuk’s reasons: the influx of trendy new bars and restaurants, a smattering of celebrity sightings, and relative affordability.

Unfortunately, Teodorczuk’s arguments show that he has no understanding of what most urban young people actually think is cool. What makes the Upper East Side appealing to bankers and unappealing to artists, and thus condemned to cultural mediocrity, is not a dearth of celebrities or fashionable eateries. The cool kids are attracted to diversity, dynamism, tolerant liberalism, and transit accessibility. The Upper East Side is uncool because it is mostly populated with rich white people, it is too expensive to live there as an aspiring artist or to open an experimental business there, and it is too hard to get to the happening neighborhoods from there. It is still appealing to some young people, the kind for whom street safety, snazzy interiors, and proximity to their office is more important than having diverse or cool neighbors. In most cities, where rich white people didn’t hold down an urban neighborhood, those people are typically found in suburbs or the quasi-suburban periphery: places like West Hartford, Conn., Arlington, Va., and Manayunk in Philadelphia.

Here are a few choice quotes from Teodorczuk’s article, which lay bare a lack of New York knowledge so striking that you’d think this Upper East Sider of seven years had just stepped off a spaceship:

  • “The UES celebrity quotient has also upped its game. … Emma Watson, Johnny Depp, Mila Kunis, Daniel Radcliffe, and Katie Holmes have all been spotted in Upper East Side bars and eateries this year.”
  • “The blueblood traditionalists, pompous dowagers, young families, overweight frat boys and overpaid lawyers are still found in the area between Central Park and the East River. But the Upper East Side is also buzzing thanks to a spate of restaurant, bar and retail openings belatedly supplying sting to the once predominantly WASP enclave. … a hotter scene ranging from the recently opened Meatball Shop between 76th and 77th streets on Second Avenue to The Mark, the stylish bar in the Mark Hotel on Madison Avenue at 77th; from gastropubs Jones Wood Foundry and The Penrose to cocktail bars The Gilroy and Infirmary and steakhouse The Arlington Club.”
  • He quotes an “Internet entrepreneur” and Upper East Side resident named Mark Dorosz, who says: “We’re infused by the Hispanic wave from Harlem rather than gentrified bullshit from Bushwick. I’ve got Saudi friends coming to bling it up and they’ve always stayed at the Gramercy Park Hotel, but they’ll now be at the Mark Hotel. Nightlife is shifting geographically and the Upper East Side is sucking it up. … Brooklyn is more segregated than the Upper East Side. Here it’s so diverse — there’s affordable housing for a young crowd that wants to live in Manhattan and then the most tony apartments on Fifth Avenue’s Golden Mile.”

OK, point by point: Seeing celebrities or Saudis blinging it up in a neighborhood is evidence not of its coolness but of its trendiness. When the gossip pages start telling the masses about spotting a boldface name somewhere, that’s when the place goes from cool to trendy — if it was ever cool in the first place — and the cultural followers supplant the leaders. (Do you think it’s cool to see your neighborhood in the pages of People magazine? I don’t.)

Since the Upper East Side has been fancy since before there even were celebrities, it never had a period of underground cool before they arrived. And since celebrities are rich people, they live in rich neighborhoods. I have an ex-girlfriend who grew up on Fifth Avenue downstairs from Bette Midler and a few floors up from Kevin Kline. Spike Lee and Woody Allen live in the neighborhood. Teodorczuk claims Gossip Girl is the only pop-culture depiction of the Upper East Side as a glamorous, rather than stultifying, setting. This would imply that he’s never seen Lee’s 25th Hour, Allen’s Manhattan, Metropolitan, The Wackness, or Cruel Intentions, nor has he read The Bonfire of the Vanities or Bright Lights, Big City. Especially if he read the latter book, or anything else by Jay McInerney, he would know that the Upper East Side’s heyday of coolness was back in the 1970s and ‘80s, when most of New York City was so blighted that young aspiring novelists could afford to live and party on the fringe of the Upper East Side.

There have always been bars and restaurants — especially steakhouses — in the neighborhood. And the fact that 10 years after a trend like cocktail bars is established in the Village it finds its way Uptown is nothing remarkable. At this point, there are cocktail bars in Spokane, Wash.

Dorosz, the author’s random interview subject presented as some sort of expert, is making demonstrably false claims about the Upper East Side versus Brooklyn. The Upper East Side is not, in fact, more diverse or more Hispanic than Bushwick. According to their respective Community Boards, the Upper East Side is 79 percent non-Hispanic white, 3.2 percent black, and 7 percent Hispanic, while Bushwick is 8.5 percent non-Hispanic white, 20 percent black, and 65 percent Hispanic. This would seem to undercut Teodorczuk’s peculiar notion that the Upper East Side’s WASPiness is somehow reversed by the arrival of a Meatball Shop.

More importantly, it hints at the Upper East Side’s single greatest flaw: its people. Look at a map of New York City election results, and you can see that it is the only Republican-leaning neighborhood in Manhattan or inner Brooklyn, Queens, or the Bronx. That’s because it is the only inner-city New York neighborhood that never suffered from white flight. (All of the other conservative neighborhoods are essentially suburban enclaves in the city’s far reaches, like Howard Beach or southern Staten Island.) The Upper West Side, the Lower East Side, and most of Brooklyn’s most desirable neighborhoods like Park Slope and Fort Greene went through decades of demographic churn. The artists and professionals who gentrifried these neighborhoods were on average more diverse, and more tolerant of diversity, than Upper East Siders. That’s why those neighborhoods still vote overwhelmingly Democratic despite having grown wealthy. And that’s why they attract cooler people than the Upper East Side does.

Per Richard Florida and his “Creative Class” theory, tolerant, liberal urban areas attract and create cultural vibrancy. No city’s most Republican neighborhood will ever be its coolest. Quick, name some cool cities: San Francisco, Seattle, New York, Austin, Los Angeles. Look at how they vote and then look at how their uncool suburbs vote.

Many of New York City’s artsiest neighborhoods — first SoHo and Tribeca, then Williamsburg, Bushwick, and Long Island City — also had funky old industrial spaces that lent themselves to creative reuse. “The Upper East Side doesn’t have the building stock for a cool neighborhood,” says one Manhattan real estate agent who grew up on the Upper West Side. “You don’t have some old tire shop that you can turn into an art gallery.” That, combined with high commercial rents, makes it impossible for most innovative, creative businesses to open. “It will always be douchey,” concludes the agent. “It will always be stodgy.”

Aside from Teodorczuk’s misrepresentation of Bushwick, he offensively refers to all of Brooklyn as if it were the few slivers of Williamsburg he has seen. Notwithstanding that, Brooklyn has roughly one million immigrants, a significantly poorer and larger non-white population than Manhattan, and many more racially and socioeconomically integrated neighborhoods, from working-class immigrant enclaves like Bay Ridge, Sunset Park, Kensington, and Bensonhurst to gentrifying, predominantly African-American and Caribbean neighborhoods like Crown Heights and Bed-Stuy.

Dorosz and Teodorczuk take it as a given that the only type of diversity or integration that matters is a mix of young white professionals and older mega-rich white people. They characterize the Upper East Side as “affordable,” when it is far from affordable for working-class families or struggling artists. To cool people, though, socioeconomic and ethnic diversity is an important attribute. Cool New Yorkers – and increasingly liberals and millennials across the country — are also usually concerned with mass-transit access. The Upper East Side has only the Lexington Avenue subway line, which can be at least a 15-minute walk from the neighborhood’s eastern edge.

For aspiring artists, merely being 20 percent less expensive than the astronomical rents in downtown Manhattan isn’t enough: Housing must be actually affordable. That’s why the real next cool neighborhood will be deep in an outer borough, far off Teodorczuk’s tiny radar screen.

There are, however, positive lessons to take from the Upper East Side. One is the reason for its relative affordability. It isn’t just the ascendance of SoHo, Tribeca, and Williamsburg; it’s a matter of public policy. While the classic pre-war buildings of Park and Fifth Avenue have been largely protected from development — and thus remain extremely expensive — the less architecturally distinguished blocks from Lexington Avenue to the East River generally are not, at least along the avenues. The result: Tall, new apartment towers sprang up. Since prices are set by the balance between supply and demand, the increased supply of housing stock led to decreased prices.

By comparison, desirable neighborhoods such as Greenwich Village and Brooklyn Heights have been largely cordoned off from development to protect their gorgeous historic brick row houses. This is a credible tradeoff, but it is a tradeoff. And it calls into question the backward complaints of some activists that high-rise apartment development will exacerbate unaffordability.

It also is worth noting that every article on the resurgence of the Upper East Side takes it as a given that the far East Side’s main deficiency is its lack of subway access, and that the construction of the long-awaited Second Avenue subway line will bring higher real estate values. Higher prices, of course, reflect higher demand. And so it shows that cities can control some aspects of what makes neighborhoods cool. But the Upper East Side is not the model.