Written by Adam Rathe

Michael Kors by Michael Vollbracht

It’s fitting that fashion icon Michael Kors’ prized portrait was done by another sartorial star, illustrator and designer Michael Vollbracht. “I fell in love with his illustrations as a fashion-crazed teenager,” Kors says. This picture, a gift from Kors’ husband, Lance LePere, shows the masterful hand that landed Vollbracht as an illustrator at Henri Bendel and Bloomingdale’s. Kors notes his astounding eye, saying, “He captured the moody side of me perfectly.”

Written by Adam Rathe

Diane Von Furstenberg by Anh Duong

“A lot of artists tend to accentuate the glamorous,” Diane Von Furstenberg, the decidedly dazzling designer, says. “But Anh is very probing, honest and forthcoming in her work, which I love. I think she captured my vulnerability.” Von Furstenberg liked the portrait so much that she hung it in her New York headquarters.

Written by Adam Rathe

Peter Brant by Urs Fischer

While his wife, Stephanie Seymour, has inspired works by artists including Maurizio Cattelan, media mogul Peter Brant isn’t as open to having his portrait done. Still, he was won over by this wax statue, created by Urs Fischer for a 2010 show at the Brant Foundation Art Study Center. “It was important to Urs and to the show,” Brant says.

Written by Adam Rathe

Salman Rushdie by Francesco Clemente

Soon after Salman Rushdie relocated to New York from London, his friend Francesco Clemente, the Italian artist, painted this portrait. “I used to joke that it was too gloomy—I’m not that gloomy,” says the author and intellectual. “But that’s how Clemente saw me that day. His later portraits of me seem to have cheered up.”

Written by Adam Rathe

Christy Turlington Burns by Alex Katz

“Being painted is different from being photographed,” Christy Turlington Burns says, and she would know. The supermodel-philanthropist appreciates the collaboration that goes into a portrait like this one, which hangs in her Manhattan home. “There’s more time to talk throughout the process,” she says. “I think it feels like the essence of who I was at that particular moment in time.”

Written by Adam Rathe

Written by Adam Rathe

Lapo Elkann by Ian Berry

Dapper Italian marketing man (and Fiat heir) Lapo Elkann insists one of his prized possessions is made of denim. “It was a total surprise, organized by a close friend of mine,” Elkann says of the piece by Ian Berry, a.k.a. denimu, whose medium is the fabric. The portrait made such an impression that Elkann installed it over his desk.

Written by Adam Rathe

Paris Hilton by Marguerite Moreau McCarthy

As a child, Paris Hilton was inspired by films depicting grand mansions with portraits hanging above the stairs. “I always said that when I bought a house, I would do that,” Hilton, who runs 42 eponymous boutiques, recalls. This painting now hangs in her Los Angeles home. “I love that I look so proper, refined and elegant,” she says.

Written by Adam Rathe

Rex Reed by Bryan Organ

“Very few people can paint me,” says film critic Rex Reed, “but he got the youth, the petulance, the ennui.” Reed must have been particularly inspiring, as Bryan Organ is said to rarely paint Americans—and he offered to do this one for free.