Getting Your Portrait Painted Is Trendy Again, and It’ll Only Cost You $15,000

Once considered a relic of the photography era, the art of portrait painting is making a comeback—think of it as a selfie that takes weeks to complete.

Hedges poses for Davy.

Photographer: Clément Pascal for Bloomberg Pursuits

By his own estimation, James Hedges IV, chief executive officer of the hair salon chain John Barrett, owns at least eight portraits of himself. Some—such as the ones by photographers Carrie Mae Weems and Bruce Weber, who shot him and his son—were gifts.

Others he commissioned from artists as different as Vera Lutter, who specializes in pinhole photography, and the Brazilian artist Vik Muniz, who made a portrait of Hedges and his kids out of Hershey’s chocolate syrup.

On a September afternoon in Brooklyn, N.Y., Hedges, 47, perches on a wooden chair beneath a massive potted philodendron to sit for his ninth. Dressed in a navy blue polo, white pants, and black Nike running shoes, he positions himself in front of TM Davy, an artist who shows his occasionally candle-lit, homoerotic paintings of friends, lovers, and cats at the influential downtown New York gallery 11R Eleven Rivington. “Like this?” Hedges asks, his head turned slightly to the side and his arm over the chair’s back. “Sure,” says Davy, who’s seated in front of an easel with a neat palette of colors laid out beside him. “Whatever feels comfortable.”

Davy’s style, a soft-focus photo-realism, makes faces and bodies look as if they’ve been shot in the most flattering light imaginable—Caravaggio meets John Baeder. Although he’s gained notice for his portraits, Davy prefers to choose his own subjects, and he rarely takes a commission. But when he does, an 8-inch-by-10-inch head study in oil starts at $3,500; a large, full-figure composition can run from $15,000 to $20,000.

For Hedges, getting his portrait done is more than a mere exercise in vanity. “I’m not that interested in seeing pictures of my face,” he says, noting that only the Muniz is on display in his house. “How creepy would that be if I had an apartment filled with pictures of myself?”

Instead, he sees having his portrait done as an opportunity to be a part of the artistic process. “If I were to ask TM if I could sit for 12 hours, watching while he paints, what’s the likelihood that would actually happen?” Hedges asks. “I’m here, participating via this commission.”

Within five minutes, Davy conjures an expressive face on the blank white canvas. After half an hour, the face is recognizably Hedges. Then, for the next two hours, Davy turns the painting from something that merely looks like the man into something that communicates his personality. 

A portrait of Rosselli by Cooper

A portrait of Rosselli by Cooper.

Source: Courtesy of the Artist

Portrait painting as we know it derives from a mostly aristocratic, European tradition that began in the 13th century, born out of devotional and then dynastic purposes. But once it became commonplace among the aristocracy, it “tended to flourish among the bourgeoisie,” says Joseph Koerner, a professor of art history at Harvard. Soon, even tradespeople were getting their likenesses painted, and by the 15th century, when the Dutch artist Jan van Eyck painted the Arnolfini Portrait, in a style Koerner calls “the highest level of technical flawlessness,” portraiture had become its own genre.

Today, portrait painting occupies an unsteady perch, neither cutting-edge nor kitsch. Figurative painting is somewhat anachronistic—Andy Warhol’s portraits in the 1960s mark the last time the genre could have conceivably been called avant-garde—and yet the best portrait painters are still highly sought after, charge massive sums, and command profound respect among the very wealthy. It’s a prolific segment of contemporary art that’s been hiding in plain sight for years.

There’s a tendency to credit portraiture’s rise as a type of aspirational living, but Koerner cautions against it. Even early portraits “weren’t about the subjects’ relations to high-born people,” he says. By Rembrandt’s time, “the whole Dutch portrait tradition was that it was about who you were as an individual, rather than who you were by birth,” he says.

Ultimately, Koerner says, “portraits have long been about fame and the afterlife,” a sentiment that helps explain why the art form endures. “It’s all about coming up with a personal statement about someone’s essence,” says London-based painter Ralph Heimans. “In complete contrast with the selfie culture, which is all about the instant, the [subjects] are aware that this will last.”

Heimans, who was the only artist chosen to paint Queen Elizabeth II for her Diamond Jubilee, relies primarily on commissions, which start at $250,000. They usually come via well-connected representatives, such as Lady Penelope Mountbatten, who was married to Lord Ivar Mountbatten, a direct descendant of Queen Victoria and Catherine the Great. Similar networks operate in Hong Kong and Dubai. “When you paint one person, you enter into a milieu, and that leads to more work in that community,” Heimans says. “They’re often people who have extremely good networks and who know a lot of people who might be clients.” 

Once he accepts a commission, he’ll spend several days with his subject. (The queen was an exception, he says, because he got only one sitting with her.) “I did a portrait of a Hong Kong family, and they took me on a holiday to start,” Heimans says. “I went with them to their chalet in Switzerland”—a trip that involved a midnight toboggan ride along a mountain cliff, which the family thought would be fun. But it’s not just about bonding. “It’s also to understand the best setting for a portrait,” he says. “Many families have different homes in different countries, and you have to find the place that feels like the most natural fit.”

After the client agrees to a location, she’ll sit for one or two preliminary sessions, at which point Heimans will send drawings for approval. After those are approved, there will be one or two more sittings. Given the travel involved and that Heimans has only one studio assistant, each painting takes about a year to complete. (He paints about four large-scale portraits a year.)

Pets can also be a source of lucrative commissions. Tom Palmore, an artist represented by the LewAllen Contemporary gallery in Sante Fe, N.M., has been painting hyperdetailed portraits of animals for most of his 30-year career, after a negative experience with a Chelsea gallerist turned him off human portraits. Palmore specializes in evoking the pathos of pets both domestic and exotic.

Heimans’s "The Boyers"

Heimans’s The Boyers.

Source: Courtesy of the Artist

Of the 20 paintings he does every year, about four will be commissions, he says. Depending on the size, his portraits of pets range from about $25,000 to $35,000. “When I was younger, I would ask for 50 percent upfront and then the 50 percent if they were happy with the painting,” he says. “But now I do the sketches, then the painting, and if they’re not happy with it, I’ll just sell it in the gallery.”

Palmore’s process is much the same as in traditional portraiture, though for obvious reasons, he can’t do a live sitting. Instead, he’ll visit the pet with a professional photographer, make a preliminary sketch, and then paint the animal’s portrait. He receives more commission requests than he can agree to—and some animals he just won’t do. “I have to want to paint it,” he says. “It would take an enormous amount of money for me to paint an elephant seal, because I don’t like the way it looks.”

His business is all word-of-mouth. “I sold a painting to a man in Las Vegas [of] a reclining English bulldog,” he says. “The next thing I know, three of his friends want me to do their Great Pyrenees.”  

Where does one find these portraitists? Often, people get the idea after seeing a picture in the home of a friend.

Joanna Coles, the editor-in-chief of Cosmopolitan, commissioned paintings for both of her teenage sons after meeting the portraitist Hilary Cooper near her vacation home in rural Connecticut. And even though painted portraits are “something people really value,” she says, “it’s just, how on earth do you get one?”

Coles at Cooper’s studio in Connecticut.
Coles at Cooper’s studio in Connecticut.
Photographer: Clément Pascal for Bloomberg Pursuits

On a Saturday afternoon in late summer, Coles is sitting for her own portrait in Cooper’s attic studio in a rambling, 1850s hilltop house in Lakeville, Conn., which Cooper shares with her husband, the lawyer-turned-author Chris Crowley. The walls of the studio, which overlooks a lake and the surrounding woods, are covered with Cooper’s portraits of friends and acquaintances: a large oil painting of a 19-year-old heir to the Mellon fortune hangs on one wall; nearby, a watercolor of Patty Hearst is propped up in a corner; a bronze bust of the late novelist James Salter stands on a table in the studio.

“Hilary paints WASPs, don’t you?” teases Coles, who is dressed in a navy blue blouse, white pants, and silvery Birkenstocks. “You’re the WASP portraitist.” But that characterization isn’t completely true—on another wall is a massive portrait of a policewoman whom Cooper saw in a cafe and asked to paint, and she’s also done a series of wheelchair-bound subjects from various walks of life. Nonetheless, for a certain set that bounces between New York, Aspen, Connecticut, and Paris, Cooper is their artist of choice.


Check out 14 of Palmore's favorite commissions, which can run to more than seven-feet wide and go for $25,000 to $35,000 a pop.

Perhaps it’s her style. Her pictures look informal and feel more contemporary than what you might find in a state capital rotunda. And her brush strokes are just abstract enough so you see a subject’s tie, for instance, but not the pattern. She does about 10 portraits a year; a “basic head to hands” costs about $15,000, and her watercolors are about $5,000. Her portrait of Coles, however, isn’t a commission—Cooper requested that Coles sit because “she’s so wonderful-looking,” Cooper says.

This is Coles’s third sitting, and the painting already looks to the untrained eye almost complete. She perches in a delicate, modernist wooden chair bought at a Conran Shop and stares out a huge picture window into the woods. Cooper, wearing an apron, dances back and forth at her easel. “It’s a nice process, sitting in Hilary’s chair,” says Coles, who has a country house a few miles away. “It’s very mellow and relaxing. I’d much rather do this than sit with a therapist.”

The conversation soon turns to the nature of portrait painting and why, in Coles’s estimation, it’s experiencing a resurgence. “Luxury now is about having time,” she says. “For a portrait, part of its value is that it took the artist time, and it took the sitter time, and that’s unquantifiable. It’s so different than having your photo taken.” Friends of hers “hired a war photographer to follow them on their vacation in Rome and take pictures of them when they (in theory) didn’t know they were having their pictures taken,” Coles says. “It was literally the most absurd thing I’ve ever seen. There are all of these gritty pictures of them eating pasta in the Piazza Navona. It’s like, This is Rome, not Sarajevo,” she continues. “I thought, Why didn’t you spend money having oil portraits done?”

Another of Cooper’s clients, interior decorator Bunny Williams, has a country estate nearby, where a portrait by Cooper of Williams’s husband, antiques dealer John Rosselli, hangs in the living room. “There’s certainly a stuffiness with portrait painting,” Williams says. She gestures to the portrait, which shows Rosselli holding one of their rescued mutts. “Though this is not a stuffy painting.”

Heimans's "The Coronation Theatre: Her Majesty Queen Elizabeth II"

Heimans's The Coronation Theatre: Her Majesty Queen Elizabeth II.

Source: Courtesy of the Artist

The perception of formality—that portraits are just for retiring judges and university presidents—is what one company, Portraits Inc., is trying to change. Founded in 1942 by a New York socialite named Lois Shaw, the company acts as an agent for almost 100 portrait artists across the country. Not quite a gallery, Portraits Inc. is closer to an agency, connecting artists with patrons, negotiating sitting times, and coordinating payment.

The company, which has headquarters in Birmingham, Ala., and satellite galleries in New York and Flat Rock, N.C., will facilitate 500 to 600 portraits a year, says its executive partner, Julia Baughman. Oil portraits start at $3,000 and can go as high as $100,000, she says. “It’s based on artist and size.”

While acknowledging a “strong portrait tradition in the South,” Baughman is adamant that New York and its suburbs offer a rich vein of subjects eager to be immortalized in oil. Instead of hyperformal, stiff-backed paintings, Baughman says she’s seeing a transition to “cleaner pieces” that feature simple clothes—a cocktail dress instead of a ball gown, say—and a plain-colored background. “I think that’s definitely influenced by contemporary art,” she says.

Davy, Hedges’s portraitist, works in this aesthetic. He’s not quite Portraits Inc. material, as his art is informed by gay and lesbian themes, and it subverts (and sometimes amplifies) the drama, humor, and eroticism of Renaissance portraiture.

As Davy and Hedges finish up their three-hour sitting, Hedges looks at the painting. “I know exactly what I’m going to do with it,” he says. “I’m moving into an apartment that is extremely contemporary, white terrazzo flooring, white cabinetry, white walls, and this is going to look like a rich, Old Mastery jewel.” He pauses, staring at his likeness. “It doesn’t really matter that it’s me.” 

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