In the early 1980s, the designer Tommy Hilfiger met the artist Andy Warhol. “He brought me to his Factory and showed me his art,” Hilfiger recalled on a telephone call. “At the time, I wasn’t in a position to buy it, which is too bad, because it would have been a great investment.”

Three decades later, Hilfiger has become what he euphemistically describes as “self-sufficient” (having sold his namesake company for $1.6 billion in 2006), and he’s emerged as a dedicated art collector.

“I like to buy and sell all the time,” he said. “I’m very interested in knowing who’s who, and what something is worth, and whether or not it would have a resale value.” But, he added: “I never want to buy something and just leave it in storage.”

To that end, Hilfiger, who estimated that he has about 50 artworks spread across his houses in New York, Connecticut, and Miami, is selling five major works at Phillips’ 20th century and contemporary art evening sale on Nov. 16.

Hilfiger’s top lot is a 1987 painting by Jean-Michel Basquiat, Untitled (Devil’s head), which hung in the foyer of his Manhattan apartment. Hilfiger said he bought the work after seeing it at Art Basel Miami Beach.

“I was just totally attracted to it,” he said. “I thought it would look great in my apartment because of the red, black, and silver—it really complements the decor.”

The painting, the value of which is estimated at $3 million to $5 million, was painted during Basquiat’s preoccupation with Pablo Picasso’s art, which, Hilfiger said, makes the painting doubly exciting. “It’s really irreverent and just amazing,” he said. The Basquiat market has recently shown remarkable resiliency. Earlier this month, the artist's 1982 work, Hannibal, sold for $13.2 million at Sotheby's in London; this spring, a massive work from 1982 sold for $57 million, above a high estimate of $40 million, at Christie's in New York.

The second-highest lot is a stained-glass style mosaic made out of butterflies by Damien Hirst: Disintegration–The Crown of Life, from 2006. Hilfiger bought the artwork at Phillips in 2011, bidding, he said, from the auction floor itself. (That in itself is a rarity; high-profile collectors prefer to bid by phone.) At the time, Hilfiger paid just over $1.4 million for the artwork, and now appears willing to break even on his investment. its current estimate is $1 million to $1.5 million.

“Sure, Hirst isn’t at an all-time high,” Hilfiger acknowledged. (Hirst's market plummeted after he flooded the market in a self-organized auction the day Lehman Brothers collapsed. As yet, prices for his artworks have yet to substantially recover.) “But I think it has substantial value.”

The next two lots have identical $700,000-to-$1 million estimates. The first, an abstract figure on fiberglass by Jean Dubuffet, Le Gommeux, hung prominently in Hilfiger's Miami office for several years.

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