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Tommy Hilfiger

It's fitting that Tommy Hilfiger's red, white, and blue logo is a riff on the United States flag: His brand is built on the American Dream. The look has always been about clean-cut sportswear, with a knowing twist and wink. His fabrics of choice are the classics of that genre—khaki, madras, and seersucker—and you can always count on him for a rugby sweater or navy blazer in case your arms get chilly in one of his little Ivy League shirtdresses.

In the mid-nineties, Hilfiger's fortunes rose to the heights during a crossover moment in which displaying his preppy logo on the exposed top of your boxer shorts became an early equivalent of bling-bling. Hilfiger courted the hip-hop crowd with million-dollar runway extravaganzas and a heavy dose of trends. In more recent catwalk expeditions—chastened by changing times and tastes and a subsequent fall in his company's stock price—he's sought the approval of the fashion establishment, showing more ambitious separates. But whomever his audience, Hilfiger's love for life and country is as bright and upbeat as his starry front rows.

The second of nine children, Hilfiger was born in the town of Elmira in upstate New York in 1951. Skipping college, he got into the rag trade at the age of 18, when he and some friends piled into a VW Beetle to drive to the city to pick up bell-bottoms and sell them at a profit to the kids back home. Soon they were running a chain of stores called People's Place, but when bell-bottoms went out of fashion the chain went bust. Unfazed, the ambitious and unschooled garmento moved to the city to start his own line. After reportedly turning down jobs designing for Calvin Klein and Perry Ellis, Hilfiger launched his menswear collection in 1985 with an ad campaign infamous for its chutzpah. In it, he counted himself, a totally untested unknown, among Ralph Lauren, Calvin Klein, and Perry Ellis as one of the top four designers in the country.

Fast-forward ten years, and the CFDA was naming Hilfiger its Menswear Designer of the Year. A successful womenswear line followed in 1996. These days, after all the peaks and valleys, Hilfiger still designs. He's an active philanthropist, he's starred on reality TV, and his stars and bars are almost as ubiquitous as Old Glory itself.

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