Mickey Drexler on Taste, Intuition, and Building Iconic Brands

Hello Monday with Jessi Hempel

Careers, Business

4.8 • 1.1K Ratings

🗓️ 18 August 2025

⏱️ 32 minutes

🔗️ Recording | iTunes | RSS

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Summary

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.

Transcript

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0:00.0	LinkedIn News
0:02.1	I was on a Charlie Rose show years ago, and he asked me a question like that.
0:10.9	How did it feel to be fired like that?
0:13.6	I said, it's their opinion and not mine.
0:18.3	And who knows what went behind that?
0:21.3	And I never thought of that before.
0:23.7	But hello.
0:27.5	From the news team at LinkedIn, I'm Jesse Hempel, and this is Hello Monday.
0:32.0	It's our show about the changing nature of work and how that work is changing all of us.
0:39.3	Today, friends, we're going to talk about taste. What is taste exactly? Well, it's not pattern recognition. It's not merely studying.
0:46.9	If those things matter to taste, artificial intelligence would be pretty good at it, and we all know
0:51.3	that AI bombs at taste. Now, taste is something magic.
0:57.9	It involves talent. It involves intuition. It involves a little bit of everything. And something
1:04.3	else, something that cannot quite be described and measured. Today's guest is among the most significant tastemakers of our time.
1:13.9	He's Mickey Drexler. Now, as I was coming up in business reporting, I always knew of
1:19.3	Mickey and even at the beginning of my career, he was already legend. He's the reason that
1:24.4	Cackeys and Button Downs became a thing in the 90s.
1:30.2	He invented Old Navy, if you can believe it.
1:34.0	And after all of that, he got fired.
1:41.7	And just in that moment when he would think that he could back into an easy career of golf games and martinis in the evening, Mickey leaned in.
1:45.0	He took over Jay Crewe and built it into a powerhouse. He launched Madewell.
1:46.0	Half the jeans in my closet are made well.
	...

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