As we near the end of Fashion Week, we’ve invited some friends and experts to join us in a lunchtime conversation about the origins  and current state of college fashion. We will be using the discussion tool Branch, and the conversation will begin in this post at noon.

Joining us:

Richard E. Press, columnist at ivy-style.com, former CEO of J. Press, consultant at the FIT Museum
Amy Levin, founder/creative director of CollegeFashionista.com
Lawrence Schlossman, editor at Complex and co-writer of the forthcoming book Fuck Yeah Menswear
Scott Lipps, president of model agency One Management
Mary Alice Stephenson, style and beauty expert
Peter Davis, editor-in-chief of Scene magazine

http://branch.com/b/ivy-style-and-the-state-of-college-fashion

Joining us:
Peter Davis, editor-in-chief of Scene magazine
Scott Lipps, president of model agency One Management
Mary Alice Stephenson, style and beauty expert
Kelly Cutrone, of the fashion PR world and America's Next Top Model judge

So check it out here! Our lunchtime Branch conversation on Fashion Week Etiquette.

http://branch.com/b/fashion-week-etiquette

"Manhattan is an ever-evolving island, especially when it comes to real estate," e-mailed Ms. Dannenberg, who will serve as the new publication's CEO and publisher. "In the days of Henry James, the social set lived in what is now known as Greenwich Village and from there they moved to Edith Wharton's Chelsea and onward to the Upper East Side.  [But] we are no longer defined by where we live. We are not an Upper East Side magazine, but a magazine for the affluent household, not defined by neighborhood or by age but by mutual interests and similar demographics. What Manhattan needs is a magazine written and styled for the affluent, stylish, intelligent and savvy man or woman who can and does only exist in New York."

The new publication will cover social events, luxury style and New York personalities. "We will be at every movie premiere, black tie charity benefit, hot night club opening and in the front row of every fashion show from Alexander Wang to Oscar de la Renta to tell who said what to who, and why they said it," said Mr. Davis, via email. "News breaks by the tweet in Manhattan, so expect updates on the digital horizon as well as print. We are fascinated with what's next, whether it be a hotel (we already have the insider scoop on The Standard's new East Village location), to a handbag, to the girl of the second that has the style world swooning. We will keep you talking and guessing all year, and all night long."

"The three of us are thrilled to be given the opportunity to create and entirely unique and unexpected magazine," added Ms. Burns, via email.

Ms. Dannenberg, Mr. Davis and Ms. Burns are all Manhattan natives and Ms. Dannenberg pointed out that they're all ostensibly part of the demographic they're also targeting. "Peter Davis is a Buckley boy, has over 15,000 Facebook followers, and has written for every prestigious magazine on the planet," said Ms. Dannenberg. "He is always the most popular man at the party. Cricket Burns is herself a Sacred Heart girl with two Sacred Heart girls of her own. She has worked at Harper's Baazar, Seventeen, Quest, Luxury Finder.com. and AVENUE magazine."

Ms. Dannenberg spent over 23 years at AVENUE with breaks in-between to work as Publisher at start-ups Manhattan File,and Luxury Finder.com and in-between, she was Publisher at Quest.

"I'm excited to work with a team that has already demonstrated success," Mr. Kushner said, "And I look forward to seeing what I know will be a creative, smart and stylish publication."

Ms. Givens, for her part, has a powerful reason to stay in the city during the summer: she's a full-time, practicing associate attorney at the esteemed Cravath, Swain and Moore firm. Her brother, Matthew Reeve, has also been keeping busy: he's in a three-year graduate program at NYU, which he'll be leaving with dual Master's degrees in film and business, and which includes an intense summer session. "I just realized, I can't take any credit for this event in any way!" Mr. Reeve exclaimed. (A companion affectionately corrected him: "That's not true at all.")

When we asked Mr. Reeve what he'd been reading, he rattled off some very dry-sounding textbooks: The Independent Producer's Survival Guide; Basic Statistical Ideas for Managers. ("Great cure for insomnia," he offered.) Mr. Reeve is well-rounded, though; he said he'd also been reading Josh Waitzkin's The Art of Learning. "He was a former chess champion who then gave up professional chess and started tai chi," Mr. Reeve explained.

Speaking of memoirs, we also chatted with Francesco Clark, founder of the Clark's Botanicals skincare line, who's just released his own. Walking Papers, which details both the spinal-cord injury that left Mr. Clark wheelchair-bound and his painful, remarkable recovery process, arrived on American shelves June 3, and will launch in Russia, China and the United Kingdom in three weeks. The characteristically cheerful and polite Mr. Clark described his ordeal as, all things considered, a positive thing. "I'm getting better — I'm using my wrists now. I'm involved in a research study at MIT, a robotic research study," he said. "I don't know, I forget about my injury... life has to move on. And so my summer feels like your summer."

Apart from actor Hayden Christensen, the event drew mostly gorgeous media types: we spotted Louise Roe, erstwhile Olivia Palermo competition on The City and current host of The CW's makeover show Plain Jane, along with Allure editrix Linda Wells and men-about-town Peter Davis and Kristian Laliberte. But it was Paper's Mickey Boardman we couldn't help approaching; we were drawn to his jewelry. Over a lime-green polo shirt, Mr. Boardman wore an eye-catching, oversized green bib necklace.

Fenton, maybe?, we speculated internally, before Mr. Boardman beat us to the punch. "Joan Rivers for QVC!" he announced proudly. "My mom sent them to me. This color story is 'peacock.' I also have them in pink."

So What's Tinsley's role on the show?

She's playing herself. I think it's sort of tongue-in-cheek. Tinsley lives the life these kids portray on the show only they're much younger of course.

Where was it shot?

It was at a soundstage in Brooklyn, not the Hamptons.

What was the context of the scene?

She said it was a sort of party scene, some kind of party where everyone is in all white. I think it was like a virginal reference not a reference to Puffy, you know alluding to how innocent everyone is, or rather how terrible all these kids are.

Did the producers give her any lines?

In the scene, she interacts with Blair. She has a few lines. I think she's supposed to be like an older version of what they are, almost like a shout out to themselves.

Does this mean she might pursue an acting career now?

I think Tinsley should definitely be an actress and Hollywood needs someone like her, with all the trailer trash out there. I think they could really use a good WASP like Tinsley.

The contest—which gained a bit of heat last week when Page Six reported on socialites' efforts to stack the votes in their favor—closes with four finalists: Publishing heiress, model and bag-designer Lydia Hearst faces off against socialite/style writer Derek Blasberg, and Lauren Davis, socialite and Vogue editor, faces off against Peter Davis, the mocialite-loving ... style writer!

Conclusions? OK, the media totally stacked this thing. And! The mocialites are ascendant. And? Lydia Hearst.

Who can claim the title of 2007’s most socially social New York society clan? In a major year-end party wrap cobbled together by Style.com, the aesthetically-inclined Web site asks—and, thank gawd, answers—that very question.

On one side of the party divide is the Peter and Minnie Davis/Tinsley Mortimer team. (Mr. and Ms. Davis are, for those who didn’t know, Ms. Mortimer’s siblings-in-law.) On the other: Ann Dexter-Jones and her three party-hardy kids—Samantha, Mark and Charlotte.

As Style points out, it’s been quite a year for both clans: Topper and Ms. Mortimer’s wedding got a major write-up in the Times; and Ms. Davis tied the knot with Syriana director Stephen Gaghan. (What they don’t mention, however, is that 2007 was also the year society scribe Mr. Davis found true love in a certain young social, Paul Johnson-Calderon.)

Meanwhile, Mr. Ronson’s single, Stop Me, climbed to the number-two spot on the British charts—no small feat, to be sure. What’s more, Samantha Ronson was, for a while anyway, queen of the tabloids, soaking up the buzz as her friendship with Lindsay Lohan continued to heat up. And then there’s their younger sis Charlotte, who we caught up with not long ago at her Nolita boutique, where she was introducing her 2007 Resort collection. Ms. Dexter-Jones, too, told us all about her new lease on life post-divorce, loving the high-thread-count sheets at her new digs in the Bowery Hotel.

In the end, though, there can only be one winner; (as Heidi Klum might say, “You’re either in or you’re out.”) And in this case, Patrick McMullan must pick the winning bunch—“that ultimate litmus test of social visibility.” While the Dexter-Jones/Ronson squad racked up an impressive 422 photos credits on the social shutterbug’s Web site, the Davis/Mortimer clan reigns supreme. The trendy trio said "cheese" for Mr. McMullan’s lens a whopping 732 times.

“Going to India for a month without phone or Internet access was even more appealing as I could finally escape any association with that site,” he wrote in an e-mail on Nov. 28. Mr. Blasberg said that he was now in London, where he’d stopped off for a few days after traveling in India with his friend, the model Jacquetta Wheeler.

The plan didn’t go quite as smoothly as he might have liked. Days before his trip, he sent out a mass e-mail informing his many friends that he would be out of e-mail and phone contact. One recipient, Lauren Davis, mass-replied, according to socialiterank.com, inquiring “how Socialite Rank would be updated now that he is gone in Taj Mahal land.” The site went on to speculate that the slight would set off a feud of epic proportions.

Indeed, in today’s socialite milieu, there are few worse things than to be fingered as the author of the anonymous Web site.

“It’s become something that is pitting friends against friends,” said a certain “It” boy who asked to remain anonymous. “You see someone you know and you like, and you have to wonder: ‘Wait, can I talk to that person? Is he involved in the site?’ It’s made going out much less fun.”

Bring on the suspects!

“I am a full-time publicist, not a part-time blogger. I don’t even have a computer at home,” said Bonnie Morrison of KBK, who has also been named as a suspect. “My friends and I are always hazarding guesses about who’s behind it. One time a friend had a laptop sticking out of her bag at a dinner party, and we all started make jokes that she was doing socialiterank.com.”

So who is behind the site? The Web site only conducts interviews by e-mail “due to our strict confidentiality,” someone wrote from its e-mail address, and its proprietor signs its e-mails “SR Team.”

“It really has become the best parlor game of the season,” said Ms. Morrison. “I’ve heard people say Peter”—that’s Peter Davis—“but I’ve also heard people say Hud Morgan. And he always accuses me of doing so, so I’m going to give it right back to him and go with Hud.”

Men’s Vogue writer Hudson Morgan would not comment for this article.

“All I know is that I don’t do it,” said Peter Davis, a fashion features director at Fashion Week Daily. “I heard that it’s hosted in Germany and registered in Pennsylvania, so whoever’s behind it has obviously gone to lengths to cover their tracks.”

“People think that it’s me because Tinsely [Mortimer] is rated No. 1 and she’s my sister-in-law,” he said.

“Derek Blasberg is the kind of talented Mr. Ripley who would write this,” said one boy about town.

“I don’t even know how to blog,” said Douglas Friedman, photographer and regular partygoer. “It’s a ridiculous site to begin with; I have nothing to do with it.”

Faran Krentcil, a Fashion Week Daily chick, is another suspect. Some believe she writes another anonymous socialite blog. “You can polygraph me and make swear to every deity in the world,” said Ms. Krentcil. “I think if you read everything, you’ll see it’s not my style.

“Plus,” she said, “I would have ranked Julia Roitfeld a lot higher. She would have been my No. 1. I think she’s fabulous.”

“It’s a great, great guessing game,” said full-time hostess-helper Andrew Saffir. “They very nicely profiled me. They just e-mailed me from a nebulous e-mail.”

“What I think is kind of cool is that they’ve kept it anonymous,” said Olivia Palermo, 24, who, when she is not wearing expensive dresses, is studying history at the New School. “You’ve got to give them props for that.” Ms. Palermo is currently lurking at No. 25 on the list.

Mr. Davis recently attempted to clear his name by offering an expensive group meal to the individual who outs the Socialiterankers.

“Dinner for 12 at Waverly Inn to whoever outs SR. XXOO. Let the game begin,” he wrote in an e-mail subject line. The text in the body of the e-mail was a recent Radar Online article titled “Poorly Ranked Socialite Hires P.I.”

But was she really so poorly ranked? Multiple sources have said to The Transom that Lauren Davis had indeed hired a shamus, a bloodhound, a flatfoot to investigate the site. “It’s pretty much common knowledge that she’s the one who hired the private investigator,” said one source.

“I have absolutely no comment about it,” said Ms. Davis, when asked whether she’d hired the P.I. “I feel bad for you and your editors and your readers. There are much more important things in the world.”

Ms. Davis did, however, reveal an up-to-date knowledge of the postings on socialiterank.com. She did not wish to comment on the site further.

Ms. Davis is currently ranked at No. 12, down from her earlier ranking of 7.

“It’s almost good that I offered this dinner, ’cause people are really turning up the heat,” Mr. Davis said. “I just thought it was funny to raise the stakes.”

Controversy centers on the talkback section, in which readers are allowed to post their comments. For instance, the Oct. 20 “Blasberg and Davis Exchange Nastiness, Start a Huge Feud” post received 124 comments.

“I can’t fault him for disliking Lauren, though … who doesn’t?” wrote in someone calling herself (or himself) Caroline Bingley.

The nastiness of the comments has weight for these gal-abouts, because many of the people reading and possibly commenting are members of their social circle.

“I think it was kitschy and sort of fun in the beginning, but the person or persons that started it have allowed the site—particularly the comments boards—evolve into something hurtful and, for a forum that reports and prides itself on being connected to the upper echelons of American society, completely classless,” said Mr. Blasberg.

“Everyone reads it, of course,” said Fabiola Beracasa. She is currently ranked at No. 2 on the site.

“Paris Hilton brought to light the existence of the socialite to Middle America and the world. Before, it was either models or actresses—but socialites were, most times, born into this lifestyle. That’s what fascinates people. It’s a continuous lifestyle that people are fascinated by. But it’s not all the media’s fault,” she said. “You know, it’s us posing for the cameras and going out and exploiting the spotlight for our careers.”

Alfie

It was a rough holiday for Fabiola Beracasa. New York’s No. 2–ranked socialite recently lost her right-hand man, a longhaired Chihuahua named Alfonso, when he was struck by a car at 64th and Lex.

The accident happened on Nov. 14. Alfie was two years old. The family butler had been transporting him to the vet. He had Alfie cradled in his arms as they approached the doggie hospital’s entrance.

“I guess when Alfie saw that they were going to the hospital, he squirmed and tried to make a run for it,” said Ms. Beracasa, who is the creative director for Circa, an antique-jewelry firm. “What happened was he ran into the wheel of a passing car and broke his little neck.”

Ms. Beracasa has spent the last week recuperating at the family house in Palm Beach. She had been planning to go to Japan, but she was too distraught and canceled the trip. “For a while, I couldn’t get out of bed. There’s such an incredible bond you make with a dog.”

“He was the sweetest dog,” said Ms. Beracasa. “I would be just holding him and I would tell my boyfriend, I would be like, ‘Jason, I want to change his name to Neo because he’s like the One. He was like a person, not a dog.”

Ms. Beracasa holds no ill will toward the butler, who has been with the family for over 15 years. “It could have happened to anyone,” she said.

By random coincidence, her boyfriend, Jason Beckman, had only recently bought a longhaired Chihuahua for himself. “He’s been trying to give her to me. He sees me crying and he’s like, ‘I don’t want you to be sad.’ We might name her Anouk. There’s a model named Anouk, but it’s not after her. I just like the name.”

—S.M.

Trumpsgiving

The Trump family deviated from tradition this year and spent Thanksgiving dinner at the Mar-a-Lago clubhouse. It wasn’t the same as Grandma Trump’s famously enormous home-cooked turkeys—“Sometimes they wouldn’t fit in the oven, they were so big,” said Eric Trump—but the vast buffet at the Palm Beach club had its advantages.

“We always joke that our family are all big saucers,” Mr. Trump explained. Eric, 22, is the youngest of Donald and Ivana’s brood, the little brother of Donnie Jr. and Ivanka. “We love drowning our food in gravy, so we were grateful that it was buffet style—otherwise we’d constantly have to be ordering more gravy, which would be kind of embarrassing.”

“We’ve got a phenomenal chef down there,” he said. This was by phone, on Nov. 28. The Transom is pretty sure that his mouth had begun watering and that he licked his lips at least once while talking turkey. “It was delicious. There were yams, stuffing, cranberry sauce, delicious peas and carrots, cakes—and they’ve got one of the best pastry chefs in the world at Mar-a-Lago. It was just an amazing, amazing meal.”

There was no mention of wine. The Trumps don’t drink.

Rounding out the Trump table in the main dining room that night was 8-month-old Barron, in a “standard baby outfit,” and Donald Sr. and Melania. All were in formal dress. Ivanka was off traveling in Chile. Donnie Jr. and his pregnant wife, Vanessa, were celebrating their one-year anniversary in Mexico.

They were there in spirit. “There was a lot of talk about the baby. You know it’s certainly going to transform the family. You know he or she is going to be the first in a whole new generation of Trump. We’re all very excited.”

But on that night, it was just two half-brothers of the same generation, the original baby brother and the new baby brother, all going head to head against the gravy boat.

“He’s a typical Trump: He was slamming down those mashed potatoes,” said Eric of his new little brother. He was about to walk into a meeting on a building or a new project or some such. “We’re all big eaters in our family. I can tell that Barron’s going to keep up that tradition. My mom used to joke that it was more expensive to feed me than to pay for my education.”

Oh, you know you’re curious!

Eric graduated from Georgetown last May. He took a couple months off to travel and, just a couple months ago, quietly started working for dad. It’s what he’s always wanted to do. He feels it in his veins.

“I always say it’s the Trump gene. As far back as I can remember, I loved Legos, and I’d always erect the most elaborate Lego cities,” said the bright-eyed, baby-faced new executive when The Transom ran into him at one of his first public events earlier this month. Like Donnie, he has an ample head of hair, but his is blond and he spikes it up. “It’s just something that’s in our blood.”

He said he’s currently working on projects in Chicago, Dubai, Las Vegas and Mexico. “I’m constantly traveling, and I really enjoy it.”

And he’s thrilled to be working side by side with his big brother—particularly now that he has the advantage when it comes to horseplay. “Donnie, being six years older, beat me up all time and, you know, I loved it and we’re still best friends to this day.” Today, li’l bro has at least three inches and 20 pounds on Donnie Jr. “It’s a lot of fun now that I’m bigger than him. We still push each other around a little bit. It’s great, it’s healthy, especially when we work together 24/7.”

All the young Trumps have their defining interests and characteristics: Donnie enjoys the outdoors and rock-climbing, Ivanka likes clothes and stuff, and Eric has his tool collection.

“I was always fascinated with tools. I still love tools. I always tell people: ‘For Christmas, I want gift cards for Home Depot,’” he said.

It wasn’t easy for the young lad to choose a favorite amongst his vast collection. He said it would definitely have to be a woodworking tool. He hemmed and hawed for a nearly a minute. “I really like my chisels,” he said.

—S.M.

The Transom Also Hears ….

On Monday night, outside Lovely Day on the Lower East Side, Mary-Kate Olsen and her scruffy arm candy, Max Snow, were having a private party in her enormous blacked-out S.U.V. A witness reports that the couple were acting about as sloppy as one of those awesome bag-lady dresses the diminutive twin favors.

“They were yelling stuff and laughing,” said the observer, who also noted that Ms. Olsen was wearing a fur coat, a fedora and some Balenciaga boots. “Then four of her girlfriends came out of Lovely Day, and they all got in the S.U.V. Before leaving, they threw a bunch of crap out the window—some cups and bags, but also a whole roasted duck. Like the kind you see in Chinatown. It was totally gross, but also kind of funny, because of course what else is Mary-Kate going to do with a roasted duck?”

Out west on Saturday night, the Spur posse was once again regulating on La Cienega. The über-bachelor crew of Leonardo DiCaprio, Kevin Connolly and Lucas Haas showed up at Hollywood’s AREA after 1 a.m. A guest reports: “Leo and his friends acted like they owned the place. They demanded a booth and had Lily Semel kicked out of hers so they could sit. Her dad runs Yahoo! Those guys need to check their egos. They’ve gone from being the cute young actors that are the life of the party to a few old guys trying to score with young babes. It’s kinda pathetic.”

—S.M.

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.”

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.”