Roll Over, Dürer: Portrait Painter Eneas Capalbo Turns ‘It’ Girls Regal

“You see she looks like Madonna and child, no?” said the artist Eneas Capalbo. “No, really—it’s all about what the face inspires me to do, eh?”

Mr. Capalbo, now 30, grew up in Buenos Aires and speaks with a thick accent. He was kneeling over his portrait of the socialite Fabiola Beracasa. The delicate pencil-on-paper drawing in question did indeed depict Ms. Beracasa gazing downward serenely, as if on a child.

He had laid out several portraits on the floor of his Upper East Side apartment. The petite artist—he is not much more than five feet tall—was now crawling amongst them, explaining his technique. “I tell them to look this way, look that way, until I get the position I want,” he said, referring to a portrait of gal-about Mariana Rust. Ms. Rust’s profile was directed upwards.

“Imagine that 200 years passed, and let’s say that people don’t know who these girls are—it’s just like an Old Master,” he explained. He produced an art book on the Old Masters to demonstrate the similarity. “She looks like a saint or a martyr. It doesn’t matter that they are society girls or whatever.”

Over the last year, Mr. Capalbo has more or less cornered the market on socialite portraiture. He recently had a show at Valentino, exhibiting some 50 of the drawings. The list of subjects comprised a number of socialites and art patrons, including Tara Rockefeller, Annie Churchill, Dayssi Olarte de Kanavos and Marjorie Gubelmann. It also included some “It” girls, like Tinsley Mortimer, Zani Gugelmann and Amanda Hearst.

“We thought it would be a great way to spend an evening appreciating beautiful art and also incorporating the Valentino clientele,” said Graziano de Boni, the president and chief executive of Valentino USA. “It was very chic, and all the girls were very pleased.”

According to Mr. Capalbo, the idea for the Valentino show came about naturally in conversation one night last spring at the club Double Seven. He was there with some of his society girlfriends and Mr. de Boni. The exec, who has since become a good friend of Mr. Capalbo, heard about the drawings from the girls; the rest is history.

But Mr. Capalbo might deserve a little more credit for his success. He came to the States 10 years ago. While he was vague on how he was able to stay afloat initially—his mother is a history professor and he doesn’t speak to his father—he did gradually scrape his way to a certain standing in the art world. Recently, a cocaine-themed painting of his hung in the men’s room at the Gagosian Gallery as part of artist Dan Colen’s exhibit, Cocaine Paintings. Perhaps of equal importance, he has become close friends with a number of society girls in recent years and can regularly be found immersed in a bevy of them at a table at some exclusive nightclub.

“I only go to Bungalow or Double Seven,” said the artist. He has deep-set eyes, and his mouth is perpetually on the brink of a smile. He also claims to dine only at Le Cirque and Elaine’s.

“He definitely embraces the social side of the art world,” said Casey Fremont. She is 23 and works at a nonprofit art-production fund. Her father, Vincent Fremont, represents the Warhol Foundation. “I love going out with him—and he’s an amazing dancer.”

Ms. Fremont said that since she met Mr. Capalbo a little over a year ago, he has drawn her, both her parents and her boss, Yvonne Force.

“He’s a character on the scene,” said Peter Davis, a fashion writer who recently befriended Mr. Capalbo. “He’s small, he’s hard to miss, he’s always got a smile on his face, but yet he’s kind of removed. He’s definitely become a bit of a socialite. He’s kind of following in Warhol’s footsteps.”

So, Mr. Capalbo, are you a socialite?

“Fuck you,” the artist responded, with a smile. “It’s not a joke. It’s just a continuation of a classical tradition.”

By one definition or another, Mr. Capalbo is indeed pretty classic. When at work on his drawings (he also paints), he draws from home. He rises at around 9—unless he’s had a particularly late night—showers and then puts on a suit. All his suits and shirts are tailor-made by Sills on East 53rd Street. He slips into a pair of his Belgium loafers and takes a quick walk around the block to get the blood flowing. Then he sits down to his desk, his pencil and paper, and his camera lucida—a drawing aide used by artists in the 1800’s. He special-ordered it from London.

Mr. Capalbo will spend up to several days on a single subject. He takes multiple pictures of a subject’s face at different angles. Then he sketches a number of the poses and settles on his favorite one. At present, the camera lucida is focused on a picture of Michael Rockefeller.

He is adamant about defending his artistic integrity. He points to his idols, from Dürer to, yes, Warhol. “If you look at old paintings, that’s what painters did—they painted patrons. Now everybody wants to pretend: ‘I do what I want—I’m a rebel.’ Why? I like patrons. You should be straightforward about it. They are good. Without them, art wouldn’t exist. That’s what art is for, for people who have the time and money to enjoy it. I don’t agree with people who are coming on the weekends to the gallery to see show. What is that for? They should be watching TV. TV is for those people.”

As for the “It” girls: “Some are young girls, and they are young and they are cute, and why not paint a cute face?” he said.

There is another, similarly classic idea behind the concept of drawing socialites: They have money. “I think, you know, he’s painting girls he thinks are pretty and interesting and have the money to buy them,” said one “It” girl who asked to remain anonymous.

Mr. Capalbo’s gallery on West 22nd Street, Newman Popiashvili, sells the portraits for $5,000, but he said that he usually sells them to friends at a reduced rate. Of the roughly 100 portraits he’s done, Mr. Capalbo said he’s either sold or traded half of them.

And business is booming. Many socialites have discovered that a Capalbo portrait makes for a great Christmas gift. He’s currently been commissioned to do a number of entire families, the names of which will remain nameless—so as not to spoil the surprise. Past families have included Stephanie Seymour, her husband Peter Brant and their brood.

Art collector Jane Holzer is a big fan of Mr. Capalbo’s portraits. She should be, considering she provides him with an art studio downtown. “He’s done my whole family. There is a buzz about him. He’s also done a spray-paint portrait of me,” she said, referring to a previous era in Mr. Capalbo’s work, whereby he would paint a canvas a flat color and then spray-paint the person’s name on it.

“I think he’s capitalized on the socialite scene, which is in overdrive at the moment,” said Mr. Davis. “People love lists and love to be included and hate not to be included. These people get photographed constantly, and this just adds another picture to their collection.”

“It has sort of become a sort of badge of honor among a certain crowd to have had him do your portrait,” said the nameless “It” girl.

Indeed, when Mr. Capalbo goes to his beloved Bungalow, he is routinely asked “by some young girl” for a portrait.

“I usually say, ‘I’d love to,’” he said, smiling. “And then I find some way to get out of it. I pick the face. The face has to speak to me.”