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Paul Mittleman, former VP of Design and Creative Director at Stussy, joins Justin Jay on The Plug for an in-depth conversation about the real origins of streetwear, skateboarding, and subculture.

From collaborating with Shawn Stussy to helping shape the creative DNA behind Supreme with James Jebbia, to working with Adidias and Converse, Paul offers a rare insider’s perspective on how authentic creativity and underground community built modern street culture.

He reflects on the early days of Stussy’s surf and skate roots, the rise of Supreme in downtown New York, the misunderstood label of “streetwear,” and how Instagram and algorithm culture have transformed personal expression.

Whether you’re a designer, sneakerhead, or student of culture, this is an essential conversation on authenticity, creative integrity, and the people who shaped the language of modern streetwear.

Chapters
00:00 Intro – Without Stussy, there’d be no Supreme02:30 Connecting Shawn Stussy and James Jebbia to NYC’s creative scene06:00 The rise of Supreme and its Stussy influence09:30 Why Stussy and Supreme stayed authentic13:00 The “rude” Supreme store culture explained16:30 The birth of drop culture and limited collabs19:00 “Future Landfill” – The dark side of hype22:30 Why “streetwear” is the wrong word26:00 Can subcultures still exist in the algorithm era30:30 From downtown discovery to TikTok trends36:00 Instagram, identity, and creative curation46:00 Integrity over corporate success49:00 Paul’s pick – “Subculture” by Dick Hebdige

About The Plug
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The Plug w/ Justin Jay is a bi-monthly arts and culture podcast featuring unfiltered, long-form interviews with the artists, entertainers, and innovators shaping today’s world. Each episode explores career challenges, inspirations, and the stories behind music, sports, design, and politics.

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Follow the audio podcast of The Plug w/ Justin Jay every other Thursday → https://www.theplugwithjustinjay.com

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Topics: music production, New York City history, hip-hop history, creative process, professional surfing, comedy, photography, arts & entertainment

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