We sit down with Mickey Drexler — the retail legend who built the modern American wardrobe. Over an 18-year run he grew Gap from $400 million to $14 billion in sales, founded Old Navy and turned it into the fastest brand ever to hit $1 billion, personally bought the Madewell name for $125,000, and later ran J.Crew. Steve Jobs put him on Apple's board, where he helped design the Apple Store — and then called him the night before Gap fired him with one day's notice. Today he's chairman of Alex Mill, the brand founded by his son.
Mickey opens up about his cameo on Breaking Bad, why Jackie Kennedy was his muse at Ann Taylor, the Paris moment that gave Old Navy its name, why Gap Kids was a mistake, the loudspeaker he installed at J.Crew headquarters, and why he thinks AI will never replace human taste. He also explains the one thing he says he'll never stop doing — and the rule he lives by that made khakis cooler than jeans. Plus: his pick for the best fashion brand he never worked for, and the advice he'd give anyone going into business with family.
CHAPTERS:
0:00 - Intro: Mickey Drexler on Building Gap, Old Navy & J.Crew
1:38 - Mickey Drexler's Breaking Bad Cameo, Explained
4:47 - Mickey Drexler, Ralph Lauren & Calvin Klein: The Bronx Fashion Story
11:51 - Mickey Drexler at Ann Taylor & His Jackie Kennedy Muse
14:09 - How Mickey Drexler Turned Gap From $400M Into $14B
23:33 - Why Mickey Drexler Says Gap Kids Was a Mistake
25:41 - How Old Navy Got Its Name & Took On Target
37:45 - How Mickey Drexler Bought Madewell's Name for $125,000
41:29 - Mickey Drexler & Steve Jobs: Designing the Apple Store
48:05 - How Steve Jobs Warned Mickey Drexler He'd Be Fired From Gap
49:27 - Mickey Drexler on Running J.Crew & Being a Micromanager
54:45 - Old Navy's American Flag T-Shirt & the Business of American Style
58:42 - Mickey Drexler on Why Fashion, Food & Fitness Live on Fads
1:04:08 - Mickey Drexler: Why AI Can't Replace Human Taste
1:06:19 - Mickey Drexler on Alex Mill & Working With His Son
1:07:29 - Rapid Fire: TJ Maxx, Best Business Book & Timeless Style
1:10:52 - Mickey Drexler's Takeaway on American Fashion
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