Aug 22
1h 6m
Doug talks with longtime friend Andrew “Andy” Hilfiger about building culture at the intersection of fashion and music, from early retail lessons with his older brother Tommy Hilfiger, to creating Tommy Jeans, and his own brand, Andrew Charles. Andy recounts key moments in his career, including styling hip-hop and R&B artists, launching iconic campaigns with Aaliyah, and how Snoop Dogg ended up wearing his designs on Saturday Night Live. He tells Doug about launching J.Lo by Jennifer Lopez, and remembers where he first met Doug... on Britney Spears' Baby One More Time tour. Andy shares advice on how to start your career in the fashion industry and reflects on changes driven by e-commerce and fast fashion in recent decades.
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Original Publish May 26, 2026
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