Caroline Astor: The OG socialite of New York

For months now, my steady assault on the social world had provided me a healthy diet of Krug and canapés.

Not this time.

“We’re giving you a book report,” said my editor. That sounded suspiciously like work.

“You won’t make it any further in society until you know what it is, where it comes from,” he said. “You’ll just hit a wall. Having no idea what you’re doing is charming, but only to a point.”

So instead of dressing up and going to parties, my mission was to find out everything I could about the history of New York’s upper crust.

A bit of Googling informed me that society in New York essentially dates back to “Mrs. Astor’s 400,” a reference to the number of fashionable guests that the OG hostess, Caroline Webster Schermerhorn Astor, and social arbiter Ward “Fun Times” McAllister decided could comfortably fit into Mrs. Astor’s ballroom back in the 1860s.

But beyond that, I was lost. Union Square’s Barnes & Noble was surprisingly sparse when it came to books on the genesis of New York’s upper crust, except for a few Edith Wharton and Truman Capote paperbacks. I was more defeated than Mrs. Astor after her daughter was excluded from the Vanderbilt Ball—in retribution for her having snubbed the Vanderbilts in the first place (which might be where we get the term “baller,” though I need to double-check that.)
So I tapped a guru, heading out for a one-martini lunch at Palm Springs West with Jamie Figg, a lawyer and social historian. A meal seemed so much more stimulating than poring over a bunch of dusty books, anyway.

Mr. Figg is a handsome man with white hair, a nice suit and a long-standing berth in New York’s social order. After I mentioned having attended Evelyn Lauder’s recent memorial, he reflected that she was one of the best hostesses he had ever met, citing her incredible attention to detail. “I remember one party she hosted back in Palm Springs, with just 40 people,” he said. “And everything was perfect. The seating, the flowers, the place-settings … You know for really good hostesses, it’s an art. It’s a job.”

With a father from Virginia and a “Yankee” mother, Mr. Figg had a unique historical perspective on New York society. He suggested that if the South had won the Civil War, New York wouldn’t be looked at as the high-society bastion that it is today. (Another reason to thank Abraham Lincoln.)

“New York was always a mercantile society,” Mr. Figg said. “It wasn’t the landed gentry, so to speak. It was really the Erie Canal that lead to it becoming a boom town, because it allowed people to get to the West without going over the mountains.”

Mr. Figg paused over his Ahi tuna salad. “Have you watched Downton Abbey?” he asked. I had. “It really captures how stifling British life was in the Edwardian period up until the first world war. Old Knickerbocker New York, with Edith Wharton being part of the Jones family … It was all very low-key. It was a very incestuous and inbred society.”

“Almost like the Windsors,” I quipped.

“Well, the crème de la crème of the day was the British aristocracy,” he said. “So New York was copying everything the British were doing, to create an upper class in a Democratic nation. Which is funny, because most of them had left England under not the best circumstances. And you know what I always say ...” he prompted.

I waited.

“Nobody has ever left the old country because they had it so good over there,” he chortled.

So one might think that anyone who managed to acquire a pile of dough would find himself accepted into late-19th-century culture, right? Isn’t that what we fought a war about, to unshackle ourselves from the chains of monarchy? We didn’t create the term “nouveau riche” (it sounds pretty French), but we did float Molly Brown. And while Edith Wharton was shrugging off her infamous maiden name—it’s where we get the phrase “Keeping up with the Joneses,” FYI—and writing scathing critical commentary about the gold-plated, corset-laced culture whence she’d come, families like the Astors, the Rhinelanders, the Joneses and the Vanderbilts were working overtime to create a “new England,” duplicating as best they could the rigid class structure that would help preserve their own position.

As one American countess sang, “Money can’t buy you class.”
That was Real Housewife LuAnn de Lesseps, of course, who knows all too well that the process more readily works the other way: class can buy you money … or at least fame, which is plenty bankable. And if it’s eventually revealed that you aren’t royalty after all—as when we discovered that the reality show star had lost her title when she divorced the French Count Alexandre de Lesseps before the show began—well, so what? There’s a whole history of “fake it ’til you make it” poseurs who have moved to New York with the dream of infiltrating the upper echelons of society by acting as if they were someone important.

These days, nobody wants to be known as a socialite. It’s demeaning. Handbag designer … interior decorator … publicist—that’s more like it! But back in the day, society was a way for women to step into the spotlight. The Edwardian model for ladies was to run their households away from the public’s hungry gaze. It was only with the first stirrings of feminism that they managed to convert social position into “It Girl” status.

“Women really became more visible when you could actually see them,” author Deborah Davis told me. “Meaning, when society was closed and elite, and played itself out in private events, women had less autonomy. It was a famous truism that you’d hear about a lady only three times in a paper: when she was born, when she got married, and when she died.”

Ms. Davis is the author of Gilded: How Newport Became America’s Richest Resort and Party of the Century, about Truman Capote’s famously decadent Black and White ball in 1966. (His invite list made Mrs. Astor’s 400 look like the guestbook at Ellis Island.)

Credit the gossip columnists with turning society into a media phenomenon. Around the turn of the century, Ms. Davis said, women were suddenly allowed to go to department stores unchaperoned (this was in the days before Spencers Gifts) or at least with another member of genteel society. And when respectable women started stepping out, people—and, more important, journalists—started paying attention to what they were up to.

“You can almost pinpoint the moment of transition,” Ms. Davis said. “When Theodore Roosevelt became president in 1901, he said his wife, Edith, would divorce him if he made her appear in a newspaper.”

At the same moment, she added, “her stepdaughter Alice Roosevelt was appearing in every newspaper. She was a sensation. Songs were named after her, dances were named after her. Every single thing that she did was chronicled. And that’s the cusp … that’s when everything changed.”
By Ms. Davis’s approximation, Ms. Roosevelt at 16 was society’s original “It Girl” because she was as interested in gossip and publicity as it was in her. She’s the lady responsible for the oft-quoted line, “If you can’t say anything nice about anybody, sit next to me.”

“If you want to learn the origins of New York’s socialite culture, you have to go back through the gossip pages of the time,” Ms. Davis suggested. In 1919, the “fat, vain” Maury Paul (as he was called in his obituary in Life magazine) began writing under the pen name Cholly Knickerbocker at Hearst’s New York Journal American.

Mr. Paul had two claims to fame. He created the term “café society”—or swiped it from Lucius Beebe, depending on whom you ask—to refer to America’s early socialites, hangers-on who adopted a “bright young things” persona without actually coming from money or contributing to society themselves. And he started the trend of society journalists who become more rich and famous—or infamous—than the subjects they write about. At the height of his career, he was earning $100,000 a year, making him the highest paid gossip columnist of all time, after you adjust for inflation (and, yes, that includes Mary Hart).

Following in his footsteps you had Igor Cassini Loiewski, the brother of Jacqueline Kennedy’s designer Oleg, who also used the pen name Cholly Knickerbocker, until he was “outed” and disgraced for using his Kennedy connections to get hot tips. Simultaneously, you had Aileen Mehle using the Knickerbocker surname (first name Suzy), for another Hearst publication, the New York Daily Mirror. Ms. Mehle started writing in the late ’50s but made a name for herself (and for Suzy) in the ’60s. During that time gossip-mongering became an art and an almost respectable trade: there was Liz Smith (who took over the Cholly Knickerbocker ghostwriting duties, and is still very much in the game), Nancy Randolph at the Daily News, Hedda Hopper and Louella Parsons duking it out on the West Coast, plus Walter Winchell. And eventually, according to Ms. Davis, you had journalists like Tom Wolfe dancing to the café society tune. These were the people who could make you famous, and in doing so make themselves even more famous, eventually becoming all but indistinguishable from the old-money figures and celebrities they were writing about. And yet not a single one of them—from Mr. Paul to today’s incarnations, like celebrity blogger Perez Hilton or New York Social Diary eminence David Patrick Columbia—had been born into American aristocracy.
No wonder it was so hard to find cohesive histories of New York’s gilded families—nobody from the inside was talking!
On the other hand, learning about the faux-Knickerbockers gave me hope. After all, they helped turn New York into an actual meritocracy (depending on your definition of merit) by gradually becoming the arbiters of who was in and who was out. In the ways that mattered, they came to wield more power than anyone in the Social Register.

So if writing about the well-bred and beautiful can perhaps help turn me into someone who gets written about, who am I to knock the job?

It at least seems a preferable route to social approval than the more common path, becoming what Ms. Davis called a “pilot fish” by attaching myself to someone already in the scene and gaining entry by association.

Then again, if you spot any whales, do send them my way.
dgrant@observer.com