In this episode of The Retail Pilot, we sit down with Gene Pressman, a third-generation leader behind the iconic Barneys New York, to unpack how a single store became a cultural force. From redefining American fashion to championing emerging designers, Gene shares the behind-the-scenes decisions, risks, and creative instincts that shaped Barneys into more than retail—it became an experience.

Gene reflects on growing up inside the business, learning from his father and grandfather, and helping transform Barneys from a men’s discount store into a global destination for innovation, humor, and uncompromising taste. The conversation spans pivotal moments like discovering Giorgio Armani, building the women’s business, creating unforgettable windows and advertising, expanding globally, and navigating the realities of rapid growth.

This is a candid, thoughtful look at creativity versus data, risk-taking versus safety, and why true merchants don’t give customers what they ask for—they give them what they don’t know they want yet.

Show Notes

• Gene Pressman’s role in transforming Barneys New York into a cultural and retail icon

• Growing up in the Pressman family and learning the business from the ground up

• How Barneys introduced American audiences to designers like Giorgio Armani, Comme des Garçons, Dries Van Noten, and more

• The shift from men’s fashion to building a groundbreaking women’s business

• Why humor, irreverence, and creativity were central to Barneys’ DNA

• The decision to take advertising and creative in-house and what made Barneys’ campaigns unforgettable

• Expansion to Madison Avenue, Los Angeles, and Tokyo—and the challenges that came with growth

• Balancing creative vision with financial realities in large-scale retail

• Why data can’t replace instinct in merchandising and brand building

• Reflections on legacy, culture, and what Barneys represented beyond shopping

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For the full story behind Barneys’ rise, challenges, and lasting impact, check out Gene Pressman’s memoir They All Came to Barneys.

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