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Building on the success of his first shop, People's Place, Hilfiger had established a chain of 10 speciality stores in upstate New York by the age of 26. During the Seventies, he turned to designing and for a period worked for Jordache before launching his own label in 1985. An astute businessman with a talent for publicity, Hilfiger's first ad campaign, which cost him $3 million (??1.8m), prompted a flurry of interest, after it proclaimed him as one of the "Four Great American Designers for Men", along with Perry Ellis, Calvin Klein and Ralph Lauren. By 1990, sales of Tommy Hilfiger clothes had topped $25 million (??15m).
Until the early Nineties, Hilfiger's market profile was similar to that for Calvin Klein: predominantly middle-class, middle-aged, mid-American white males. However, after his designs were picked up by young Afro-Americans, gangsta rapper Snoop Doggy Dog appeared wearing a Tommy Hilfiger shirt on the premier US TV show Saturday Night Live in 1994 and his sales rocketed overnight. The implications were not lost on Hilfiger. He quickly began to design baggier, more casual clothes to meet the new demand for the emergent streetwear styles. In 1995, Hilfiger was named Menswear Designer of the Year by the Council of Fashion Designers of America.
Today the growing Hilfiger fashion empire, supplemented by fragrances and other merchandising spin-offs, is worth more than $400 million (??240m) a year. Meanwhile Hilfiger is known to spend much of his spare time including his 50th birthday in March 2001 - and money on the Caribbean island of Mustique.
In July 2000, he announced that he had "mutually and amicably" separated from his wife of 20 years, Susie. The two have four children together.