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>
&nbsp;
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

The World's Most Dangerous Morning Show, The Breakfast Club, With DJ Envy, Jess Hilarious, And Charlamagne Tha God!

The World's Most Dangerous Morning Show, The Breakfast Club, With DJ Envy, Jess Hilarious, And Charlamagne Tha God!

The Breakfast Club

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

This week, Doug answers a listener question from Jasmine in Washington, D.C. about breaking into the luxury industry. He explains that luxury has distinct culture and philosophy from fashion and operates within an unwritten hierarchy. He shares five tips for getting your foot in the luxury door, including that the hiring process can take up to a year.

DM Doug:

@DougMelville

www.DougMelville.com

This week, Doug answers a listener question from Jasmine in Washington, D.C. about breaking into the luxury industry. He explains that luxury has distinct culture and philosophy from fashion and operates within an unwritten hierarchy. He shares five tips for getting your foot in the luxury door, including that the hiring process can take up to a year.
DM Doug:
<a href="https://www.instagram.com/dougmelville/">@DougMelville</a>
<a href="https://www.DougMelville.com">www.DougMelville.com</a>

Breaking Into Luxury: Secrets and Strategies for Success - A Mailbag Episode

https://api.omny.fm/orgs/e73c998e-6e60-432f-8610-ae210140c5b1/clips/9aab8883-6d05-478b-933f-b4c6008009e2/transcript

Everyone is talking about AI—but are you actually getting better at using it?

In this mailbag episode of DM Me with Doug Melville, Doug answers a listener who wants to improve their AI skills but doesn’t know where to start. His answer: create your own AI Fingerprint.

An AI Fingerprint is the unique process you develop for using AI to think, research, create and make decisions. Doug breaks down how to build yours—from defining the problem and choosing the right AI platform, to refining prompts, comparing outputs across different models and adding the one ingredient AI can’t replicate: your own judgment, experience and point of view.

You don’t need to become an AI expert. But in a workplace increasingly shaped by AI, you do need to understand how you work with it.

AI literacy may soon matter as much as knowing how to use email, PowerPoint or Google - and the leaders who develop their own process now could have an advantage later.

DM Doug:

@DougMelville

www.DougMelville.com

Everyone is talking about AI&mdash;but are you actually getting better at using it?
In this mailbag episode of&nbsp;DM Me with Doug Melville, Doug answers a listener who wants to improve their AI skills but doesn&rsquo;t know where to start. His answer:&nbsp;create your own AI Fingerprint.
An AI Fingerprint is the unique process you develop for using AI to think, research, create and make decisions. Doug breaks down how to build yours&mdash;from defining the problem and choosing the right AI platform, to refining prompts, comparing outputs across different models and adding the one ingredient AI can&rsquo;t replicate:&nbsp;your own judgment, experience and point of view.
You don&rsquo;t need to become an AI expert. But in a workplace increasingly shaped by AI, you do need to understand how&nbsp;you&nbsp;work with it.
AI literacy may soon matter as much as knowing how to use email, PowerPoint or Google - and the leaders who develop their own process now could have an advantage later.
DM Doug:
<a href="https://www.instagram.com/dougmelville/">@DougMelville</a>
<a href="https://www.DougMelville.com">www.DougMelville.com</a>

Need to Improve Your AI Skillset? Create an AI Fingerprint. Here’s How - A Mailbag Episode

https://api.omny.fm/orgs/e73c998e-6e60-432f-8610-ae210140c5b1/clips/0c18bee4-d3bc-4988-b4c9-b4bf006b8827/transcript

Doug answers a mailbag question from Janelle, a New York City professional who lost her corporate job and is struggling to find a new full-time role in this brutal job market. Sharing five practical tips drawn from his Stanford GSB reputation management teaching, Doug emphasizes that reputation precedes you, urging a Google first-page audit, and considering private social media settings. He notes that “ghost jobs” are on the rise, and with them, the rising importance of referrals. Doug advises proactively activating your network and understanding whether you’re in the “tennis” or “golf” phase of a career.

DM Doug:

@DougMelville

www.DougMelville.com

Doug answers a mailbag question from Janelle, a New York City professional who lost her corporate job and is struggling to find a new full-time role in this brutal job market. Sharing five practical tips drawn from his Stanford GSB reputation management teaching, Doug emphasizes that reputation precedes you, urging a Google first-page audit, and considering private social media settings. He notes that &ldquo;ghost jobs&rdquo; are on the rise, and with them, the rising importance of referrals. Doug advises proactively activating your network and understanding whether you&rsquo;re in the &ldquo;tennis&rdquo; or &ldquo;golf&rdquo; phase of a career.
DM Doug:
<a href="https://www.instagram.com/dougmelville/">@DougMelville</a>
<a href="https://www.DougMelville.com">www.DougMelville.com</a>

How to Find Your Next (And Hopefully Last) Job - A Mailbag Episode

https://api.omny.fm/orgs/e73c998e-6e60-432f-8610-ae210140c5b1/clips/d7063811-3194-4b13-8b68-b4b8007d0922/transcript

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

DM Me with Doug Melville

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