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Tommy Hilfiger started his retail career with a store called the People’s Place in his native Elmira, New York. It expanded to a chain of ten locations before going bankrupt. He then moved to New York City and launched his eponymous label to almost immediate media interest. He also gained the interest of the rap community, who took to wearing his clothes many sizes too large.

“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.” – Style.com

Here’s his 2010 Spring Collection:

Source: New York Fashion