Mickey Drexler on Taste, Intuition, and Building Iconic Brands

Hello Monday with Jessi Hempel

Taste might be the most valuable skill in business today. But what is it, exactly? And how do you know if you have it? In this episode, Jessi Hempel sits down with legendary retail executive Mickey Drexler to explore the magic behind great taste—and how it shapes products, brands, and careers.

Mickey is known as the “King of Retail.” Over his decades-long career, he transformed Gap into a 1990s style powerhouse, invented Old Navy, revitalized J.Crew, and launched Madewell. Today, he’s the co-founder of Alex Mill, a fast-growing apparel brand he started with his son.

Jessi and Mickey discuss:

• Why taste is more than pattern recognition—and why AI can’t replicate it

• How intuition, curiosity, and listening fuel creativity and business success

• Lessons from building and reinventing iconic fashion brands

• How to rebound after career setbacks

• The role of taste in spotting products that move markets and shape culture

• How to cultivate your own taste, no matter your field

Continue the conversation with us at Hello Monday Office Hours! Join us here, on the LinkedIn News page, this Wednesday at 3 PM EST.