Hilfiger's first job was at 12 years when he began selling jeans in his brother Tommy Hilfiger's store. Hilfiger’s other love is music and he has been playing bass guitar since he was a teen. In 1982, Hilfiger moved to Manhattan from upstate New York where he began to further pursue music. Andy toured with members of the Ramones, Kid Rock, and Blue Öyster Cult.
In the 1990s, Hilfiger started a division at Tommy Hilfiger USA, Inc. styling and dressing some of Hollywood’s movie stars and rock and pop musicians and sponsoring concert tours. Hilfiger also started the accessories division for Tommy Hilfiger USA, Inc., where he designed hats, bags, and outerwear, creating a multimillion-dollar business.
After a decade of work at Tommy Hilfiger, Hilfiger started a new company called Sweet Face Fashion where Hilfiger played a major role in launching the JLO by Jennifer Lopez brand. Hilfiger eventually helped to build the company to gross $250 million in sales and launched the fragrance Glow by J.Lo. Currently, Hilfiger is a partner in Star Branding, along with Tommy Hilfiger, Bernt Ullmann, and Joe Lamastra. Star Branding is a partner with Li & Fung USA in a company called MESH, under which the Andrew Charles fashion line was developed.

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