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.

For more of Andy Hilfiger:

Andy's Instagram

www.AndrewCharles.com

DM Doug:

@DougMelville

www.DougMelville.com

 

Original Publish May 26, 2026

Doug talks with longtime friend Andrew &ldquo;Andy&rdquo; 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&amp;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.
For more of Andy Hilfiger:
<a href="https://www.instagram.com/andyhilfiger/">Andy's Instagram</a>
<a href="https://andrewcharles.com/">www.AndrewCharles.com</a>
DM Doug:
<a href="https://www.instagram.com/dougmelville/">@DougMelville</a>
<a href="https://dougmelville.com/">www.DougMelville.com</a>
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Original Publish May 26, 2026

“DM Me with Doug Melville” is a direct, practical self-help podcast in which Doug Melville answers real questions with clear guidance to help listeners grow and take action on their careers, reputation, culture and life.

&ldquo;DM Me with Doug Melville&rdquo; is a direct, practical self-help podcast in which Doug Melville answers real questions with clear guidance to help listeners grow and take action on their careers, reputation, culture and life.

DM Me with Doug Melville

DM Me with Doug Melville: The Architect of 90's Hip-Hop Fashion - How Andy Hilfiger Combined Music & Fashion with Snoop, Aaliyah and More 

https://api.omny.fm/orgs/e73c998e-6e60-432f-8610-ae210140c5b1/clips/096147a0-9b50-4c41-81c6-b4560087c464/transcript