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Hilfiger grew up one of nine children in an Irish Catholic family in Elmira, a small town close to Cornell University. His initial foray into fashion was a store called "The People's Place." The store was a big draw for the local teen crowd in Elmira because it often held live broadcasts from local radio personalities, sold rock and roll related clothing including Kiss and Aerosmith belt buckles, and had a discreet head shop upstairs which sold drug related paraphenalia such as bongs, roach clips, and incense. After the business went bankrupt, Hilfiger moved to New York in 1979 to pursue a career as a fashion designer.
The building in which his store was located was torn down in the late 1990s to make way for First Arena, home to the United Hockey League's Elmira Jackals. Hilfiger reportedly contributed funding to the building of the arena, but declined to have it named after him, according to news reports from the time of construction.
In 1984 he founded the Tommy Hilfiger Corporation (NYSE:TOM), introducing his signature menswear collection. By 2004 the company had 5400 employees and revenues in excess of $1.8 billion. Hilfiger was named Menswear Designer of the Year by the Council of Fashion Designers of America in 1995. In August 2005 Hilfiger announced he was selling his company. The company was purchased by Apax Partners for $1.6 billion, or $16.80 a share, all in cash.
In 2005, a CBS TV reality show called The Cut tracked the progress of 16 contestants as they competed for a design job with Hilfiger in similar fashion to Donald Trump's The Apprentice. In the end Hilfiger chose Chris Cortez. Tommy's daughter Ally Hilfiger produced and starred in a reality show for MTV titled, Rich Girls.
Hilfiger is married and has four children. His daughter Ally Hilfiger was featured in the reality MTV series Rich Girls.
In 2000, a chainmail rumour was circulating the internet claiming that Tommy Hilfiger has made a racist remark on Oprah. The rumor was along the lines that he didn't want Asians wearing his clothing. (http://www.snopes.com/racial/business/hilfiger.asp)
In a January 2001 press release, the Tommy Hilfiger company denies that their founder ever made such a statement: "The facts remain simple and cannot be disputed. Tommy Hilfiger did not make the alleged comments, he has never appeared on The Oprah Winfrey Show and, in fact, Ms. Winfrey herself, on her January 11, 1999 program, stated Tommy Hilfiger has never been on her show nor has she ever met him.
"Most importantly, Tommy Hilfiger wants his clothing to be enjoyed by people of all backgrounds and his collections are put together with the broadest cross-section of individuals in mind. To reinforce this, he features models of all ethnic backgrounds in his fashion shows and advertisements." 
Designer Definition (from U.S Department of Labor)