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Tommy Hilfiger

A conversation with the fashion mogul and pop-culture connoisseur.

Tommy Hilfiger’s global fashion empire is rooted in a long-standing love for American pop culture. His designs reflect his early obsession with pop art and rock and roll, which he continues to cultivate today as an enthusiastic collector of everything from Warhols to vintage guitars. Also a longtime reader of Robb Report, Hilfiger recently took a break from his busy work and travel schedule to discuss his passion for all things pop.

What attracted you to pop art?

When I came to New York [City] in the late ’70s, I met Andy Warhol and was very impressed with his pop-culture view on life. I loved how he brought fashion, music, and art all together and almost made a spoof on it. I started collecting his work back then and became a more serious collector later on in life. I have many of his portraits, and I especially like the one of Grace Kelly because she reminds me of my wife. We have Muhammad Ali, Liz Taylor, Uncle Sam, John Wayne, Mick Jagger, and Annie Oakley. They all represent American icons or world icons. I love Andy’s use of color and the way he would mix brights with fluorescent colors sometimes, and then scribble over them. His use of color has been very inspirational in all of my fashion collections. I also collect art from Jean-Michel Basquiat, Keith Haring, Richard Prince, Tracey Emin, and Jean Dubuffet.

Do you have a favorite piece?

It is a self-portrait of Basquiat and Warhol from the day they met. Basquiat met Warhol, and he painted himself and Andy on a canvas and delivered it to Andy’s studio when it was still wet, and that hangs in my apartment in the Plaza. I have a few Basquiat and Warhol collaborations—two genius artists of the 20th century painting on the same canvas.

What drew you to rock-and-roll memorabilia?

When I started my first business in 1969, I was 18 and went into the fashion business because I was obsessed with the rock music scene and loved the way musicians dressed. I opened a store called People’s Place in my hometown of Elmira, New York, selling bell-bottoms and fringe vests, and hippie-rock-style clothes of the time, and I started collecting rock memorabilia. I have clothing, photographs, guitars, and gear from years past that are on display in my homes and office. It gives us inspiration for designing clothes and stores and keeps us connected to that spirit and time.

Tell us about your car collection.

I was collecting American classics like Woodies, and then in the late ’80s I became interested in Ferrari. The one I love the most is my Enzo Ferrari, the 2006 limited edition, and it is as important to me as one of my paintings because it has an aesthetic and at the same time it is one of the fastest street cars in the world. I used to take it on the back roads of Connecticut, and I brought it to the Grand Prix track in Mont-Tremblant. It is like an F/1 car for the street, and one of the most important cars Ferrari ever built. I have others, like a Bentley, a Fisker, a Mercedes from ’69, and a Range Rover Autobiography, but the Enzo is my favorite.

Where do you like to spend your free time?

I love the beach, and being on the beach is one of our favorite family pastimes. We have a home in Mustique, and it is a real isolated getaway where we play beach volleyball, bike, hike, paddleboard, and snorkel, and have beach picnics, or sometimes just lie in a hammock and read a book. We also love Miami. It is an incredible city, and there are great restaurants and shopping, and interesting people, music festivals, boat shows, and galleries.

How do you define luxury?

Luxury now is time with my family more than anything else. In this busy lifestyle, it is nice to settle back and do very little for a few days on the beach with the family. That is the ultimate luxury.