Tommy Hilfiger collects fast cars and contemporary art and loves European travel and his Mustique villa, as well as Italian food, tennis and yoga, but admits, “My biggest luxury is my jet. I can just get up and go myself. I’ve had it 10 years.”
And while his jet gives him the freedom to roam the world, he frequently finds himself in his private hideaway on the Caribbean island of Mustique, a private enclave for royals, celebrities and the otherwise superrich. Hilfiger’s villa, dubbed “Palm Beach,” is next door to Mick Jagger’s home — which Hilfiger rented on his first trip to Mustique in 1985. That’s when he fell in love with the island and its ideal weather.
In the early Nineties, Hilfiger bought the old beachfront cottage next to Jagger’s. He started renovating it, but quickly realized it was more than a fixer-upper, so he rebuilt it. The six-bedroom home with five guest cottages, all in sea coral stone, were designed and built by the late Swedish architect Arne Hasselquist, based on an Oliver Messel design. (Messel and Hasselquist were famous for their work on the island.)
The villa’s decor reflects a British colonial sensibility, with antiques from London, including some from the sale of the Duke and Duchess of Windsor’s estate, purchased at a Sotheby’s auction in 1996. Nowadays, Hilfiger and his family travel to Mustique about five times a year.
When in New York, Hilfiger and his wife, Dee, along with their one-year-old son, Sebastian, spend time at their 6,000-square-foot duplex on the 18th and 19th floors of the Plaza Hotel. The European-influenced apartment has four bedrooms, 4.5 baths, a library, kitchen, “dome room,” living room, foyer, home office and terrace. Hilfiger also enjoys the amenities of hotel life while he’s there, such as maid and concierge service, valet parking, limousine service and fresh flower delivery.
“I love living in a hotel,” he admitted. “I love the room service.”
His home base, however, remains Greenwich, Conn., where he has owned several multimillion-dollar estates over the past two decades — a far cry from his modest upbringing in Elmira, N.Y.
This past spring, Hilfiger purchased the former Hirschorn estate, a 15,000-square-foot home situated on 22 acres in Greenwich, for $31.4 million. It’s a prewar French Normandy with two double-gated driveways; rolling lawns; rose, boxwood and flower gardens, and a stone lion in front. The house has eight bedrooms; a master suite with dual bedrooms and dressing rooms; a kitchen with a breakfast room; billiard, exercise and media rooms, as well as both an indoor and outdoor pool, a gazebo and a greenhouse with a fireplace.
“I really love Connecticut,” said Hilfiger. “We like Greenwich, especially the back country. The house overlooks the Long Island Sound and the city.” Asked if he is handy around the house, Hilfiger admitted: “I’m not handy. I’m usually out playing tennis.”
His other Greenwich homes have included Denby Farms, where his ex-wife, Susie, lives, and houses on Riversville Road (across the street from Denby Farms), Mayfair Lane and Round Hill Road. In November, Hilfiger sold Stone Hill on Round Hill Road (a favorite stop on the charity house tour circuit) for $20 million. That 20,000-square-foot Georgian mansion was set on 4 acres and had eight bedrooms, nine baths, a movie theater, 2,000-bottle wine cellar, indoor basketball court, tennis court, gym, sauna, spa-treatment room and pool.
Born into a close-knit clan of nine children, family has always been important to Hilfiger, who enjoys spending time with his brothers and sisters, as well as his own brood. When initially asked if he collects anything, he smiled and said, “Children.”
Besides Sebastian, Hilfiger has four children from his previous marriage: Ally, 25, an artist and stylist for Nary Manivong, a young designer; Richard, 20, who’s a musician in Los Angeles; Elizabeth, 17, a high school senior, and Kathleen, 15, who’s in boarding school. Dee also has two sons, Alex, 16 and Julian, 14, both tennis players and away at boarding school in Italy.
Artwork is another passion. “I was always interested — now it’s an obsession,” he said. “I love Andy Warhol, Jean-Michel Basquiat, Richard Prince and Keith Haring.” His favorite piece? A Basquiat/Warhol collaboration that he bought in Switzerland.
A lover of Pop Art and pop culture/memorabilia, Hilfiger houses some of his artwork in his New York apartment and other pieces in Connecticut. In Manhattan, Andy Warhol’s portraits of Grace Kelly and Elizabeth Taylor are displayed in the living room. He owns more than 20 Warhol paintings in total, including those of Marilyn Monroe and Mickey Mouse. Hilfiger commissioned Hilary Knight, who illustrated the “Eloise at the Plaza” children’s book, to create a mural for the Plaza Hotel apartment. The apartment also boasts Harry Benson photographs of Truman Capote’s Black and White Ball that took place at the Plaza more than 40 years ago.
Cars are another hobby. “I used to have a large car collection, but I never drove them much. My favorite is a red Ferrari Enzo,” said Hilfiger. “I have a collection of cars that I enjoy.”
While Hilfiger spends a few weeks every summer in Mustique, this summer he took the family to the Italian Riviera for a month.
“We chartered a yacht and went from Saint-Tropez to Portofino, Capri and Corsica. We had the baby and all the kids,” said Hilfiger. They spent their time Jet Skiing, waterskiing and swimming, and shopped and dined at different ports.
“We fight over who gets to play with the baby. He’s so quiet and happy. All the children love him,” said Hilfiger. He said Dee’s ex-husband, Gianni, is Sebastian’s godfather, and his ex-wife, Susie, is his godmother.
Although Dee cooks, Hilfiger employs a chef, who specializes in organic cooking and travels between Manhattan and Greenwich. While Hilfiger wouldn’t exactly call himself techy, he does have a few gadgets he can’t live without, such as his BlackBerry and iPhone 4. “My son Richard lives in L.A., so we talk and get to see each other,” he said.
An integral part of Hilfiger’s lifestyle is to give back. The designer devotes a great deal of time to philanthropy and youth education. In 1995, he founded the Tommy Corporate Foundation, which gets involved in numerous charities. Most recently, he was named the First Millennium Promise MDG Global Leader as part of his commitment to Millennium Promise, a nonprofit organization dedicated to halving extreme poverty by 2015.
For the most part, Hilfiger considers himself a homebody, despite hitting the charity circuit frequently. He doesn’t even go out to the movies much.
“I’d rather watch them on DVD at home. I go out a lot for charity events, so it’s nice to stay home,” he said. On the weekends, he enjoys going places with his young son. “He loves swimming in the pool. We like taking him to the Central Park Zoo. He goes everywhere. He’s been to more countries in a year than most people have been in a lifetime,” said Hilfiger, citing the tot’s itinerary: Turkey, England, Italy and France, and Mustique.
Hilfiger said he enjoys traveling to Italy, France, England and Asia, but “I like the food in Italy the best.” His favorite restaurant in Greenwich is Rebecca’s in Glenville. Hilfiger stays in shape by doing yoga three to four times a week, playing tennis and bicycle riding. “I watch what I eat. I go bicycling in Mustique. Dee does yoga, too.”
Hilfiger met the former Dee Ocleppo through his yoga instructor on the beach in Saint-Tropez in 2005. “I invited her to a party on a yacht that I was chartering,” he said. They were married in December 2008.
Dee was born in Rhode Island and attended Southern Methodist University. “She was discovered on campus and went to Paris to model. She was represented by Karin Models,” he said. But she has since given up modeling.
“She’s my private muse and model,” he grinned. “For the fashion show, I did the Dee boot, the Dee bag and the Dee dress.”
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