The Best One Yet - 🇺🇸👕 “American Crew” — Interview with Mickey Drexler, ex-CEO of The Gap & J.Crew

Episode Date: July 2, 2026

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.Crew1:38 - Mickey Drexler's Breaking Bad Cameo, Explained4:47 - Mickey Drexler, Ralph Lauren & Calvin Klein: The Bronx Fashion Story11:51 - Mickey Drexler at Ann Taylor & His Jackie Kennedy Muse14:09 - How Mickey Drexler Turned Gap From $400M Into $14B23:33 - Why Mickey Drexler Says Gap Kids Was a Mistake25:41 - How Old Navy Got Its Name & Took On Target37:45 - How Mickey Drexler Bought Madewell's Name for $125,00041:29 - Mickey Drexler & Steve Jobs: Designing the Apple Store48:05 - How Steve Jobs Warned Mickey Drexler He'd Be Fired From Gap49:27 - Mickey Drexler on Running J.Crew & Being a Micromanager54:45 - Old Navy's American Flag T-Shirt & the Business of American Style58:42 - Mickey Drexler on Why Fashion, Food & Fitness Live on Fads1:04:08 - Mickey Drexler: Why AI Can't Replace Human Taste1:06:19 - Mickey Drexler on Alex Mill & Working With His Son1:07:29 - Rapid Fire: TJ Maxx, Best Business Book & Timeless Style1:10:52 - Mickey Drexler's Takeaway on American Fashion Hosted on Acast. See acast.com/privacy for more information.

Yetis, untuck your T's and cut off your quarters ifs. Because today's guest is the former CEO of The Gap, J. Crew, and the Apple Store, basically. We're interviewing Mickey Drexler, the inventor of all-American style. Old Navy? He launched it. Made well jeans? He created it. Outdoor voices?

Yeah, he chairmaned it. If George Washington needed quarter-oys, he'd probably call Mickey D. The Mickey D. Because Mickey's style is so fundamentally American, he makes Ralph Lauren look Canadian. Besties, no one. in business has influenced our national wardrobe quite like this man. So when Steve Jobs launched the Apple store, he asked Mickey for design advice. And no big deal.

Mickey was on Apple's board for 16 years. So he was basically Steve Jobs' boss. And in the age of AI, his tastemaker status has never been higher. Because this is the mind who made khakis cooler than jeans by tweaking a stitch. So today, on top of his wild career story, Mickey will tell us how we got the American uniform we are all wearing or right now. And he'll tell us why. ignoring the data is the patriotic thing to do.

Oh, and how to beat AI, you got to be cool. He's the Pharaoh of fashion, the chairman of Chino's, the prince of the popped collar. Jack, how about Miranda Priestley of American Prep? I'll take that. Does that work? That works? Besties, please welcome Mickey Drexler to the best one yet. This interview is the best looking one yet.

Mickey, great to have you with us. I mean, that is exciting, high energy, and I'm in it. Thank you. We've got to print that on some leather. Turn that into a purse. So we did some research on you, Mickey. And the thing that jumped right out to us is that you made a cameo on the Breaking Bad TV show. You starred on Breaking Bad?

How do you pull that off? That was my proudest moment. I'll tell you the story. You've added a lot of this stuff anyway. So I'm having lunch with a friend years ago. And he said, do you ever hear of Breaking Bad? He says, watch it. So I watch it.

And I'm in love. I'm addicted. So I call a friend of mine who then worked for Sony who owned whatever. And I said, Rob, this is the greatest show in the world. Does anyone know about this? He said, well, it's doing very real. I said, it's fantastic. So he introduces me to the CEO of whatever the entertainment company was.

Got a little friendly with him. And after about a year or so, he says, would you like? to do a cameo on Breaking Bad. Sold. I said, no. A year later. You're like, I don't want to go to New Mexico. It's hot. Because I get nervous about things like that. And he said, again, I said, why not? It could be fun. So I go to New Mexico. I go to the trailer, and I was in the trailer. Nine takes. I was a customer in the car wash.

Customer number two. Yeah. And the irony is... Wait, were you a customer? to get your car washed? Yeah, I was getting my car. Okay. Or for the other business. A real car wash place. And I was getting the car washed.

And I went to pay, and it took nine takes. Oh, only two of my fault. And she gave me the people that were laundering the money. Yeah. You know, her and Brian Cranston. So she says, oh, excuse me, you gave me too much money, and she gave me back. The overpayment. And these are people who have the cash loaded in the safe at the car wash.

So the irony is she was honest with that. And so that's it. Not bad. Not too shabby for a fashion guy. It was fun. Well, I'm not a fashion guy. I am who I am, you know. Now a quick word from our sponsor.

So you're a New Yorker is what you are. And we're interviewing right now in New York City, home of Jay Peterman, fictional fashion guy from Seinfeld. Jay Peterman, I thought he was from Chicago, but he was fantastic. Well, he's also Elaine's boss in Seinfeld. And he's famous for the urban sombrero. Remember that? Yes. Oh, he was amazing.

And Ralph Lauren, famous for the polo shirt. So what article of clothing is Mickey Drexler famous? And I should point out, Jack is famous for the linen shirt ever since he got back from his Italy vacation. It's always been wearing linen. I'll tell you what I'm most proudest in hope become I've become famous for we, Alex Mill. Yeah.

Is the lanyard holding the iPhone and the leather is Italian leather? The phone lanyard. Yes, yet he's for everyone just listening right now, not watching on YouTube. Mickey's wearing a extremely fashionable leather strap around his neck like a necklace that's holding his iPhone. It's an alternative to a fanny pack. It's part of my uniform in a way. It's a manny pack. And I never leave home without this.

It's on and around all day, every day because or else I misplace my iPhone. Brilliant. Speaking of Ralph Lauren, he's one of what Nick and I are calling the Bronx Bombers. Yeah, yeah, yeah. You, Calvin Klein, and Ralph Lauren, all born in the same borough of New York City within five years of each other. So what was it about that moment and that place that led to three of the most iconic names in American fashion? Well, you know, I appreciate that, but I never planned it. I'm still even today.

Did your parents plan? My parents, my role model, no. And, you know, I did a little research on Calvin, and I found that interesting story because I always didn't. Those were the two guys. They were the ones. Calvin and Ralph. Yeah, and then there was Perry Ellis and a few other people who were amazing. and Calvin's grandmother was a dressmaker.

Okay. She sewed, she tailored, she was a dressmaker. Checks out. His mother was extremely stylish and had a lot of style and taste. And his first job was working for coat manufacturer in New York. And he was in a freight elevator one day with the coats on Iraq. A woman from Bonne would teller who was a merchant buyer. I love those coats.

Where can I get them for Bonne would tell her? He said the name of the company. And she said, who designed them? And he said, I did. Wow. So that was that. He quit his job. He went to start this company, a design company with his partner then.

And that's the beginning of it. But then you were a Bronx kid who's into math. You went to Bronx science, which is like the ultimate math public school in New York City. How did you get into that same industry? I don't know. I always cared. I don't know where this came from,

but I always cared about how things looked. And I think it's because I lived in my fantasies a lot because I didn't like living in my home a lot. And I'd run to my cousins down the street. I was always escaping my environment. And I think part of the creativity comes from the fantasy and the escape. because I didn't want to be there and my mom was ill.

My father was what he was. And so it was very depressing for me. So I always like daydreamed a lot in school. I was in, I never liked school. I daydreamed in school about things and how things maybe should be. So I, in terms of getting in, I worked in the garment. One good thing my dad did is he not graciously made me work. Yeah.

And I work in the shipping room of the coat company, and I put tickets on coats on the buttons. And I worked hard. I went to get coffee, a chock full of nuts. I did whatever they wanted. And I always took my work, as I do today, very seriously. And I pushed myself. I didn't know all this then. And so I was in a Garmento world.

I sold razor blades. First time I ever did an entrepreneurial thing, there's Wilkinson. sword razor blades then. The razor blade was called a sword. No, Wilkinson sword. It put a sword on their first. They could have run with that. And I don't know where I found this out, but they were the best

razor blade. You could hardly get them. It's kind of like Coorsbyer. Mickey's a good salesman. I'm interested in this razor blade now. So I sold them on the street because I bought them I don't know where. And I had a little side hustle. Nice.

Wilkinson. Anyway, that was a minor thing. So I did that and I worked always Saturdays and I always was forced to work. But it was good. It was very good. And so I'm a worker. And I never give up on things now, now a million years later. But getting into the business, I did that. And when I was in college, I got a summer job at Abraham and Strauss, a now defunct department store group. part of the Bloomingdale's group, et cetera. And I went and I had nice summer salary. It was in Brooklyn.

And I loved Ken Hirsch, the buyer of jeans. And I had great time. I was working all day, being part of the mix. I had to do a project and why millinery was going out of style. I did that. And I did seriously. So after that, they liked me a lot. And this is interesting.

In your life, a moment or two will change your. your life. So having worked at Abraham and Strauss, I thought, oh, when I finished college, they all like me. I knew the team. I'll work here. So I interviewed, and then a guy in my class, I don't even remember his name, said, oh, can you set me up with an interview at Abraham and Strauss? So I called the head of HR, who I knew. And he said, oh, sure. So I run into the guy later on. I was back at school or whatever. He says, well, thank you. I got a job offer at Abraham Srauss for $11,500 a year. I was offered $11,000. I was effing furious. And I couldn't explain to myself why. But that led to me interviewing at Bloomingdale's taking the job and that was $11,500.

Now, $500 was no small thing for me. I had no money. but I like the interviewing, I like the environment, I like the people I met, and there was a great energy. And by the way, I always tell people, you got to feel that for a company you want to work for. You're a competitive guy. Actually, one thing Jack and I noticed was you had these early insights in the fashion industry.

Like when you get your big break at Ann Taylor, you said that your muse when you were having clothes made and designed was Jackie Kennedy. What is a muse exactly? We've referenced it on the pot, and should every business, no matter the industry, have a muse? I have, she was in those days the fashionist with her sister, whose name Lee Razwell.

And I would, she, her kid went to school in the upper, well, her kid who I knew then, went to school in the Upper East Side at Brerely. And I lived on East. Is her kid, JFK Jr.? No, no, it was her daughter. Okay. Carolyn. Yeah.

But she was in that neighborhood. I lived in those days in a not nice apartment on East End in 81st. You know, whatever. And I would see her once in a while around the neighborhood. I followed her once because Jackie Kennedy, you know. Yeah. And I always, and I sent her, I knew she lived at 1040 Fifth Avenue. So she was on the catalog list.

She never bought a thing from us. But you'd still send her the catalogs. Oh, yeah, of course. Even though you knew they were getting rejected every time. It doesn't matter. You know, to me, she was who I felt I wanted us to be. And that's what amuses. And that's what amuses, yeah.

And does every industry need that? Like, every business, should you have a muse so you're designing for one person? I can't answer it because a muse has a lot of different definitions. She was an inspiration. And then over time, you have inspirational people. people. It's not a democratic process on who becomes amused. It's someone who inspires you. It's what they do. It's what they design. It's emotional. Yeah, it's all an emotion to me has always been the driver of my world and the world. And I always say to people, emotional is, they say,

why do you like someone or something? I said, I can't explain it. I said, why don't you like chopped liver? It's like, how do you explain? How do I explain why I like linen shirts? Yeah, you don't have to. So, Mickey, you're a hardworking kid from the Bronx. You're emotional. You fantasize about things you don't have. You basically started in the mailroom. You worked six days a week. And eventually you become the CEO of Ann Taylor at the age of 39. 35. 35. But what makes you famous to the American public, to the fashion industry, to the business pages of the Wall Street Journal, is you take over the Gap.

Yes. The famously 1969 Gap jeans in San Francisco, California. And you were the turnaround artist. Well, I don't like that word, but go ahead. Tell us what was happening at the Gap and what you did to fix the company. Yeah, you fixed it from $400 million in sales to $14 billion by the time you left. But I didn't leave voluntarily. Spoiler.

Right. I was fired with one day notice. First of all, the first three years I was there, we went from an apartment on the Upper East Side to San Francisco. Peggy, my son, Alex, was then six years old. Last day at Ann Taylor was a Friday. I was on a flight Sunday,

checked into a hotel there, and I'm thinking, I was so nervous, anxious, ended up being quite depressed for the first few years, adjusting to the environment, the culture, and San Francisco. I stayed at Campton Place. I take a cab who knew from Uber's or cars, and it wasn't like I had an apartment, which was fine. I was checking in and out of a hotel every weekend for six months. But I never thought about negotiating the big. shot moved that people. Oh, oh, I got an apartment. So I went to the office. Now, this is the other

cultural shock. Ant Taylor office was on 57th Street at the corner of Fifth Avenue above the N. Taylor's store. I go to San Bruno Office Park. First time I was there and like... Is that south of the city? Yeah, it's south. Oh, and the view is the airport? Not glamorous. And it hit me. what the F am I doing? And it was extraordinarily difficult for me and for Peggy to adjust. And then working in San Bruno in a strange culture and the gap was fall into the gap. I used to remember it on the ads. And there I was.

I fell into the gap. Yeah. And I got there and I could only say the adjustment personally, I was very depressed adjusting to this public company where the stock was dropping because I was taking markdowns where the founder was my partner across the hall reminding me, you can't take this. And he was okay. And he built all the stores. It's a great partner.

But I would commute to the city and back. And the people in the company, they say, oh, there's the noon flight to Hong Kong. Taking off. Because he could see the airport. No one would believe this. You need the airport schedule. And I'm looking at I was there Monday through Friday

from I started Thanksgiving week and my family and my Peggy and Alex moved in June and I would commute every week. And it was like, oh my God. So back then, the company had 400 million in annual sales.

That's a little more than Albury. I never really thought of, I thought of it as a famous name as I felt about J. Crew, fall into the gap. It was crappy but famous. And I didn't like it. You know, at the age, I didn't know from anything other than what I thought. So what was the first thing you did at the gap? I sized up the culture very quickly. In fact, the first visit I took, I went to, and this says it all, you know, little way. So I travel around. So I rented a car. I rent cars. I was in Houston, Texas. I wanted to see the stores. You have to talk to people on the ground with customers. But for some reason, I end up in Houston Galleria. It wasn't fun to travel. But there's a drive I always had, and I wanted to win the race and get there. So I walk in, so I'm in the parking lot. I see windshield

flyers on every windshield. So I look at it and says, today only 30% off at the gap. Oh boy. That tells you everything. So I walked in, Hector was the store manager. I hacked her on Mickey, da, da, da. I said, what's with the 30% off?

Oh, we do that when business gets slow. That's all you need to know. Yeah, yeah. Discounting. Yeah. Everything was discounted. Fall into the gap. Levi's 2 for 26.

Everything was on sale. So what I did, I always do this. I mean, I get together with the team and I look at all the merchandise. I do that first and I meet the people. Because without the right team, I can't do this alone. No one can do anything alone. So I religiously, intensively went through every single style we owned. And I knew what I was up against it.

I mean, but I didn't, you know, but all I could think of what has to get done, I didn't think about what the fuck am I doing here. Yeah. But it was part of that. And I was miserable because the challenges and the culture and everything about it. And having a founder across the hall where the company's stock is dropping. And he said to me once, he said, well, you know, we're going to have a terrible earnings report for the first quarter because you're taking all these markdowns. I get emotional.

And, you know, but he was okay. He didn't mind. I said, if we don't take markdowns, we'll have no cash to pay the bills and buy fresh goods. You've got to convert it anyway. So the stock dropped, it probably dropped in half. Oh, boy. Now, I'm running a public company, and it was a nightmare. It was pure.

So what did I do? I had a list. The first thing I did there is every time I spoke to someone, I had no idea what they were talking about. And I knew that if I don't know what they're talking about, talking about, then no one does. Yeah. So I put on every desk in headquarters. You know, there's a keep it simple, stupid.

I put KIS, keep it simple. Yeah. The plaque on everyone's desk. I don't know if it did any good or not, but I said, I don't understand what you're saying. Yeah. And, you know, and so I just day by day, dug in through great personal

difficulties more than anything. And I just did what I had to do. You purged the bad inventory that wasn't selling. That was your first move. And I went to Levi's and said everyone in the world was mine washed Levi's, except Gap. That was the first. I started on Levi's only. And they're doing rigid washed Levi's two for 26.

And I went to Levi's and I just changed. I said, we're buying the washed goods. So you improve the genes to be Levi's quality at least. Then you eventually launch Gaveyes. Gap Kids. And, you know, it's funny, I'm a Gap Kids alum. And it's popular these days to say that you grew up chubby. People think it's like a cool thing for, yeah, they do. They really do. Jack keeps telling me this. Especially when you're handsome, good looking, great show. I was chubby. So I have a litmus test to see if people were really chubby when they were young. Here's the trivia question. I hope you know, because you launched Gap Kids. What is the largest boy's gene size that Gap Kids makes? Every childhood Husky kid knows the answer to this question. I don't know.

16 Husky. That's big. I like, I clung to those 16 huskies because I didn't want to go to like the men's department. I was only like 11. We started Gap Kids for the following reason. And it was a big mistake. We can't really. We made no money in that business.

Really? Even with Jack's family? He has three brothers who were in this husky boat. And I did Jake, crew cuts. Both mistakes. Hard to make money. Too distracting. On kids, I thought parents would be willing to pay. We thought that was a profit puppy. The reason I did gap kids. I used to take Alex shopping. Your son. Six years old. Before nursery school, I got him his wardrobe. It was always an Ashkosh by gosh, overall, which still would be great if they have and a plaid shirt. So I went to Emporium, which was no more. It was a department store in San Francisco, doing the back-to-school.

shopping, I guess in September or August with Alex who was going into the first grade. I couldn't find anything to buy, nothing. And I had a meeting back at the office. And part of it's the white space. You don't learn this how to do this. So I got together the mothers because most of them were women and mothers or a couple of fathers. And I said, as everyone, tell me about your experience buying kids' clothes. At the end of the meeting, I said to myself, we're doing Gap Kids.

So why did that not work? To make a kid's, say you want that shirt in kid sizes, it's expensive. All the details are the same, except it's less fabric. It didn't work, and kids is very much a kind of a discounty kind of business. But in the early days, we should have stopped at 10 or 15 shops, maybe. And then it's a distraction. You know, the more things that you have to do, you know, the main thing is the main thing, and kids wasn't the main thing. Interesting.

Same thing with J. Crew, in hindsight. So after Gap Kids, you would go on to launch something that worked really well. Oh, yeah. This was like the OG disruptor of fashion. It became the fastest fashion brand to hit $1 billion of sales. First brand to feel like 50 bucks, but really cost 15. Old Navy. Yeah, Old Navy.

This is a very interesting story, and it could take up the whole podcast. I'm serious. That's my favorite. Well, the Made Well, too, was another interesting story, and all of it's about how I felt. I don't want to hear negativity on this, that. So one day, I used to read in New York Times Business Section when it was worth reading. It's 25 years ago, whatever. And there was an article in it buried, maybe page four.

There was a quote, Dayton Hudson, now Target, was starting a company called Everyday Hero. And it would have prices named someone who was quoted cheaper, less expenses than Gap. Oh, boy. So it was basically a Gap knockoff. A dupe. I get on an airplane. First week it opened in Mall of America. I said, I want to see what's coming here.

Because, you know, I'm always threatened by it. This is a great story. I want to reset the scene here. Talk to me, Jack. So the predecessor to Target was launching something that was obviously intended to undercut the gap in price. A gap dupe, the early gap dupe. And so you went to Target's home state of Minnesota. Only I read the article.

Yep, only because you read the article. On page four of the time. And if they didn't have that quote, there'd be no old neighbor. And you're the first guy to scope the product and say this is a threat to the gap. So you kind of faced the innovator's dilemma there. No, this is a threat. No, when I walked in after 10. seconds, I then said, I'm not worried.

Okay. But Dayton Hudson, because we were part of the same buying group at Bloomingdale or wherever, they always did a lot of research, focus groups, this, that, I don't do any of that because I don't believe in it. I said, you know, Dayton Hudson does a lot of research to myself. He talked to yourself. I said, I wonder what went on with this thing. And I stopped off in Chicago on the way back to San, sent one.

day and I visited two stores that were in lower demographic locations. I wanted to visit the stores and I schmooze. So I went into the first shop and this wasn't a planned strategy. It was just, oh, I'm going to go to. A little detour on the trip to Midwest. I always speak to the store people. I said, why do you have so many markdowns here? She goes, this people said they can't afford our clothes. And I said, wow, bingo did the second store in another Chicago area. Same thing, bingo. Get back on an airplane. And when I got back, I don't know how I found out this statistic.

Gap genes were 3450. Every other gene in America under 30 was 80% of the marketplace. And we didn't play in that arena. We were 3450, maybe to 4450. that was a bingo. And then when I got back, because you want to know from the people, so I gave,

I don't know, it was a lot of years ago, I think maybe 200 bucks to 10 people of demographic salary and all that who worked at the gap was a big corporation.

And I signed them discount stores and I said, go and shop Mervyn's. Kmart was then, Walmart, shop, and it was stores

that are out of business. Just go spend money. And I said, spend it. And I think I gave them a category. I'm not sure. About a week or two later, they're back. And I had, you know, it was 10 of them or so. And I went around the table. And I said, report now every experience you had. They all talked about clean stores. I asked them, I used to say, Walmart used to have 987, 1322. I said, it's a matter that they have odd prices? We're pricing. Yeah. We don't care. We just want a good value, good price, and nice clothes, clean stores.

And we went around and I'm thinking, and the white space I felt early on was respect to all customers, no matter if it's discounty or not, treat people with the respect or whatever you call it. And at the end of that meeting, I was sitting there with a fellow I worked with Jeff. I didn't talk to the company about this. It was kind of my own little project. And I said to Jeff, I said, we're doing this. And that was the beginning of Old Navy. And how'd you come up with the name? So we didn't have a name. I'm in Paris. Have you heard the story? So I used to go to Europe. You get ideas. You know, being creative is exposing yourself and seeing things that inspire you. in everything.

And that's why I was inspired by this thing for need. The phone lantern. The phone landed on your shirt. I was in Paris driving back to the airport with a woman I worked with. I'm in the backseat of the taxi or whatever on Rousse Saint-Germain. And I saw a head like a movie marquee with lots of neon bulbs. And we just drove by. I said to Maggie, I say that's the name, Old Navy.

That's what was on that. A dive bar. It's a, old Navy's named after a dive bar in Paris. Yes. You saw on a taxi ride. And I checked the next day back in New York or California. Call your lawyers up. About, no one owned it.

Yeah. So I registered immediately now. Talk about things in corporations. The board didn't like them. Oh, boy. And the board's your boss. Yeah. Right.

Right. They can fire you. And they probably want to do a focus group on the name. Yeah. It's totally common. Yeah. Higher consultants. I mean, it's totally common in that sense.

But you won that battle? I'll tell you how I battled for a lot of things. When you have a family control business, I say they were great partners, but it wasn't always so easy. So the gap was a publicly traded company. Yeah. But a San Francisco family controlled. controlled by the family. And I'm still friendly with the three sons, the founder.

But so they didn't like the name, Old Navy. And then they said they, I'm not mentioning names because there are names involved here. That's fair. That's fair. And they said, well, the Gap's famous. And no one's going to know what Old Navy is. I said long story short. You know what the store opened up being called?

What? Gap Warehouse, Old Navy. That was the original name. I don't like Gap Warehouse. That's very wordy. It does not roll off the room. And I said there will be no gap in five years. Yeah.

You call the Pepsi, the Coke, and that back down. This kind of reminds me of J-Crew Factory, which I also don't like. Because I bought, for the record. When I was strapped for cash, I bought J-Crew Factory sweaters thinking they'd be J-Crew quality. But it wasn't. No? Never. And I think a similar thing could have happened to the Gap there.

If it was called the Gap warehouse and people bought it. Then the Gap... That would have cannibalizing your business. That would have cannibalized. Right. And it was a different thing, too, because the Old Navy did have more surprising things. Like, I have a bag that's made out of basketball leather, like it has the little dots on it from the Old Navy. That never would have been a Gap product.

I still have it. I still get compliments on it. You know, and this is one of the things I'm most proud of it, Old Navy. The first store that opened in Manhattan was on 18th and 6th Avenue. And I fell in love then with Schwinn bicycles. They were all very retro. They were this. So we had a Schwinn bike department around the escalator.

At Old Navy? Yeah. Sold out probably the first three or four days. Wow. And then I knew the, owner of Schwinn, a corporation, they said, we can't sell you anymore because the Schwinn dealers want people to take the bikes back to them. The Schwins, they were all yellow.

So I still have one in my garage. Sold that, but that's the kind of thing. The unexpected. The treasure hunt. It's always better than the expected in anything. My family went to that 6th Avenue store and did like, we would do halls. And you could spend like six hours there finding something like a bag. Like a basketball.

Did he maybe have shopping carts or were there big bags? I'm remembering big bags. It's a good question. I don't remember. Well, you were getting all the Husky clothes, yeah. Your family was loaned up with the four sons. I didn't make a mistake. I always wanted to have a little coffee shop in a shop.

So we put on the second floor, we got together with this restaurant guy who I'm still friendly with. We opened up a coffee shop. Well, launching kind of cooler sister brands underneath the big parent company is kind of your thing. Yeah. Like Madewell is like a multi-billion dollar jeans brand, all American brand right now. But it started in this insane way with you like personally buying the name.

TLDR. Mickey moves on from the gap to J.Crew. And Madewell is his baby. But before you start at J.Crew, you personally acquire the name Madewell. How did that go down? Well, I have a friend May, rest in peace, Dave Mullen, great guy. He was a wash expert in jeans. He worked with us at Gap and then Jay Crew.

Terrific. His job was, he was a wash expert. He's a ripped jeans connoisseur. I have a faux tear in my back pocket. Yeah. That was precision that he did. That was his art and his signs. So David calls me one day.

He shows me a wooden sign with made. made well logo it's wood and since 1937 he said what do you think of the name I said I love that it reminded me

made well it was an old workware company defunct a new bed for mass wow so he said would you want to buy it I said pence on the price because he wasn't in a position to do anything with it and I said

yeah, I would like to buy it. Oh, and the price? That was very... Can you share the price? It was $125,000. So you bought the name made well, which was based off a factory in New Bedford, Massachusetts, for $125,000.

You personally just bought it because you liked the sound of the name. And finding a great name, like Old Navy, it's a great name. Yeah. Name has to belong to the product. Namesstorming. And it's, what do you call it? Namestorming.

that. Yeah, coming up with the names. But if you think about the name, even when we name products, I want every name to be personal in a sense because they're your friend, if you remember it. And I'm trying to get the team to now just say, like we did Ludlow suits at Jay Cruz, it was Ludlow Street. Yeah, and Lori Side. And, you know, I want things to be named after streets, after this, after names that connect. It reminds when we interviewed the Harry's founder, he said branding is attention and it's a feeling at the end of the day. And each of those names, you don't need to know what they sell. They give you a feeling no matter what.

Everything is emotion. If you look at something that you want to buy, I measure. I said emotion is the most important. I don't know if it's a secret sauce. Yeah. But my heart, I said I have something inside here that tells me the bell goes off or whatever. Now a quick word from our sponsor. So, Mickey, you have gotten your big break at Ann Taylor, Jack's mom's favorite brand.

You've transformed the publicly traded Gap Company into a $14 billion. From a loser to a winner. Behemoth. Then you launched, created, invented Old Navy after a taxi ride in Paris. And you personally bought the Madewell name and turned it into the coolest jeans brand in history. Yeah. But we want to. to talk about perhaps the coolest moment we're aware of of your career, which is a phone call

you get from Steve Jobs. Yeah, because you've just been at a wine party and nap, a whining and dining and schmoozing with the guy. You know, Steve, and to this day, I couldn't love him more and just so smart, driven, and we lost a great asset in this world from him. So we met at a, a birthday party in that, but we had a home there. He was at the party. Dot, dot, da, da. And we schmozed. And I'm thinking, you know, Steve Jobs, you know, we're schmoot. That dot, dot, da, was a lot of cool stuff. Was his black turtleneck a gap? No, no. Was he wearing it at the wine party? He wore newbound sneakers and Levi's 501 was his uniform. Okay. And, but we met.

And, you know, Steve was, this is many years ago. So you two bond over both being micromanagers. Right. Well, his mission, he had a mission. And he, for a year, we chatted. And I said no about joining his board. Because, you know, at that point, I was stupid. Steve, wait, Steve Jobs asked you to join the Apple board.

And he said, he said, no, that is stupid. You said he denied his job. Because as far as I'm aware, being a. board member of a publicly traded company is three to $600,000 a year in salary. It's a good gig. For six to 12 meetings a year. Am I summarizing this incorrectly?

There's all the stock there options. Not too shabby. I was very fortunate and luck at it and think about that part of it. But, you know, it's a real part. So after a year, he calls me up and says the magic words. he said, if you join my board, and he hated boards, I'll join the GAF board. Oh. I said, deal.

And the reason is, they were all insiders. I had no say. I knew Steve, if nothing else, would be Steve Jobs. Irreverent? A little rude. Late or not showing up. Uh-huh. And it only lasted until I was fired.

It was about a year. And he's the one. So anyway, he wanted to be designed the store. What star? The first Apple's. He had a story show him. He was really ugly. So Steve Jobs shows you a design for this Apple store concept, and you think it's ugly.

It was ugly. Wow. And I said, it's too much going on. Keep it simple. And let it be timeless and let the product speak. So I suggested we get a warehouse. and build a store in the warehouse. Like a real potential Apple store.

Yeah, which we designed together. And he had an architect, whatever. And then we did it and it was the same store as today. Yeah. Because timeless for me in clothes in design never goes out of style. But I got to ask you, we've all been to the Apple store. The Apple store has not changed in decades at this point. It's the same.

Wooden tables, white walls. A lot of beautiful glass everywhere. Jack and I always say retail's not dead. Bad retail is dead. What is it about the Apple store that you designed? What resonated? What is the eternal deep feeling that we all get walking to an Apple store? That's the reason that Apple hasn't changed them in the 20 years since you designed.

You know, it's kind of like the chopped liver question. There's no answer to that. It's kind of you feel it's it couldn't be simpler, more classic, and it'll never go out of style. And style never goes out of fashion. Fashion can go out of style because fashions of the moment, you build something that looks right and perfect. You can't improve on the best.

And I think I'm not saying, you know, because I designed it or whatever, but Steve and I, that was it. Let the product speak for itself and don't look at a busy background, this, that, and the other. Keep it simple, stupid is what I always say about everything. That would have been such a great Instagram collab post. When you and Steve Jobs announced you're moving into each other's boards.

Oh, yeah. That would have been great. I can picture the photo out now. So, Mickey, you've brought Steve Jobs to the Gap board. He's brought you to Apple's board. And then the Gap fires you. They give you a one day notice and you're gone. Steve called me first.

He did? They wouldn't tell him because we were friends. and he, you know, as Steve is, he didn't go to the board dinner the night before where I show the goods. I knew the turnaround was in. We had a bad year, whatever. So I get home at 9, he goes, call Don, you're getting fired tomorrow morning. Wow. I said, no wonder, they didn't look at me at all tonight.

We were showing the best goods. I knew it was a turn. You know, and there's three companies, you know, and I looked. all that. And of course, so I go and I get handed at one sentence piece of paper. Whatever. That was, next day was my last day. But you bounce back from that and you kind of get the last laugh because you end up at J. Kru and you end up taking them public eventually. All of the growth that you sustained at the gap transitioned to J. Kruh once you started there.

And the gap started flatlining, right? I think the gap's still doing the same volume they did 20 years ago. Yeah, about $16 billion. The first thing you did at Jay Crew, we noticed, though, is you did something we've never seen another CEO do. You put a PA system into the headquarters. Loudspeaker. Loudspeakers.

Like on every floor, you know. This is Mickey chiming in. Like the principal in the middle school. Happy Friday, everybody. I didn't do it before. Why? What is it? Why did you have?

Because that seems like a micromanager kind of move. I am proud to be a micromanage. Okay, you do this and you speak to the people who speak to the customers. Now, the thing with the loudspeaker, what happened, I get there, they're ready to go, whatever, J-Crew, a disaster. And I get there and they have an office for me, a closed office. I sat there for a day. I'm bored out of my fucking mind. I'm trying to get people, I call people voicemail, this and that.

And you know something, the clock was ticking there. It feels like it's wasting time. And so I said I moved my office into an open space right outside the closed office because I hated being there alone and I was in the middle, which I did a gap towards the end. And I said, I want a loud speaker because no one's returning my call. Well, Mickey, we're publishing this episode on America's 250th birthday. Well, the annual tradition of the Old Navy American Flag Tea, that is literally American style, because you have splattered it right on there.

But, you know, we see you as also the more general visionary of American style and fashion. So more broadly, like, what is American style, Mickey Drexler? I don't know what it is. I know what style is, but about American style, I think to me, style is is defined by, what I feel or what this, you know, designing a store or designing a car. You know, look to me, the greatest brand in the world in cars is Jeep. Mm-hmm. Yeah.

But they haven't, I mean, if you think about Jeep should be the number one car, utilitarian, a workhorse, you know, consistent. And, you know, the jeeps, they redesign them except maybe for the old-fashioned one. You know, the Grand Wagoner. I mean, the Woody, they should still be doing a Jeep Woody. Oh, that would be classic. What's old is new today. Give them old and it's new. Why do you think vintage clothes look like crazy?

Yeah. So why pay the prices? Look at designer clothes pricing. And what do you get for? It's like we say the 20-year rule of nostalgia. The nostalgia moment becomes novelty. I would love to have a Jeep brand. See, the same thing connects to Gap and J. Crew.

in a way. There's a sense of brand and emotion and what you have to do, try to bring it back. Well, there is one catch there, and it's something Jack and I call the three Fs of Fads. We believe, after studying business news for 10 years, daily shows we've told you, that fitness, food, and fashion, the three Fs are the three industries most vulnerable to Fads. Time and time again, we have seen that in fitness, food, and fashion, what's hot, today probably won't be in a few years. As a Lulu Lemon shareholder, I can tell you that first hand. So we were curious, as a fashion leader, do you agree?

I'm sick and tired. What was the vegetable that everyone was eating? Was it kale? Cale? Are we on? Are Brussels sprouts? Guys, are Brussels sprouts still in? We're asking the production team.

You know, but it's true. You can't, I don't like being in that business. But you're in that business. You're in that fashion. So how do you, yeah. You know, a lot of stock market investors might avoid these engines. because it's seen that it's not possible to sustainably be profitable. You always hit a wall, but if you don't reinvent, but see, I look at products, well, look at the Levi-501, 1849, you know, they can't kill it.

It hasn't changed. That's timeless. That's unique. But no, I don't think that way. I think, look, I've had fans. My mistakes, Fast Fashion was a fan. I blew it on this. And then I have a bad year.

Stock market punishes you with a bad week. Everyone's forecasting earnings. But I don't think that way if I did, I'd get into trouble. So the way you defy fads is just constantly reinventing? Because I can, is that the answer? I'm trying to think what a fad is. There's a million of them out there. Like I look at some, without mentioning names, I look at names on a sweatshirt.

It's a fad. It'll die quickly. If it's a name on a sweatshirt. The more you show people of scarcity and I don't want to see themselves coming and going. Look at the designer logo business. It used to be, in my opinion, all due respect to my friends who were designer people, not at that level anyway. You see it coming and going. When I was a kid, young guy, starting out, it was a big effing deal when I bought my first pair of the Gucci buckle shoe in Florence.

the slip on or whatever. I walked down saying, I'm rich now. You know, because it was, but now what's unique is scarcity. And it's no longer scarce? Well, nothing,

a logo unscarses. I mean, you know. But I can see your style of reinvention right now because for the Yeti's listening, Mickey's coming here impeccably dressed in a classic Alex Mill

fashion style, but he's also wearing this leather lanyard to hold his iPhone, which you would never associate with that brand, but which they also sell. That's constant reinvention. In this case, you design for an iPhone case. And the hard thing about this business is you've got to keep doing it. Okay, but then how do you make that decision? Because what we find fascinating is Jack and I always ask our guests, you know, how do you make decisions? Metrics versus magic, information versus intuition, grass versus guts.

How much of it is imagining versus engineering? Do you go with your gut? But it starts with vision. And look, I don't. Do you look at the data, basically? Of course. The data tells me everything I need to know. I was very good in math, not science, probably. But, you know, if you look at, I don't know if AI does this,

if you feed in information that's today, it'll forecast it out. But what I do on every style, I say, what could you have sold if you didn't run out of your two best colors. Data is religious to me. Best sellers every single day tell me a story. Every day I'm nagging them to buy more of the best colors because it's not a democracy when it comes to colors or things you sell and Navy. We're out of Navy some things. They said, what's the most famous popular color for men in the world? It's Navy. And then they buy, and I asked this morning. First question, I said, how many of these did you buy of this color? And I said, give me the numbers. And they said, well, how many? I said, you should have bought at least 40%

of the buy in this color. How do you know that? You know it. So 90% of your decisions are data-based? They're always part of, because it's DNA. I look at the information. That's your gut. I always look at what's sold, even if it's three or four years old. And then there's a gut. Bring this back. On this one, it was once you, we got it, it was database. And if you sell 150 of something, you have to say, not forecasted, how many would I have sold if I didn't run out of stock in a week or two?

And that's the data that you need to look at. It's the things you didn't have and you have to estimate, and it's not a sign. but you have to forecast how many you think would sell, and then you have to protect the downside. But data is absolutely for me religion. Mickey, you mentioned AI a moment ago, and there's a quote, Jack and I love that you said. You said, AI will not write songs that move us.

So why can't style be automated? Can AI just not have taste? It doesn't have emotion. It can have taste. Well, one thing AI is, I could not do is play a salesman on Breaking Bad season two. It couldn't have pulled that off. Never. And I got $800 for that. And the residuals keep coming in. The checks are coming in. So, Mickey, to wrap up your epically fashionable resume, Abraham and Strauss, Bloomingdale's, Ann Taylor, The Gap, Gap Kids, Old Navy.

You've covered every generation. We'd love to wrap it up with some rapid fire questions. Yeah, we got some special ones whipped up, Rick. What is a timeless fashion piece that every man needs? Five pocket pair of jeans that fits him in the right wash. He needs white shirts. See, I wear this shirt, 2014. You bought that in 2014? It's still wearing.

It's custom from Hong Kong. They need white shirts. They need classic blue and white striped shirts. I always have the argument, blue and white stripe, men and women, they sell the best. He needs, I like fun socks now. The best timeless fashion piece every woman needs. You know, and I'm not a fashion designer, I think apparel, it's all about simple, elegant, no one wants to walk around saying, oh, they're wearing that purple shirt.

You don't want to be the guy or the woman. Color is critical. And I'm not qualified to say that. I know it when I see it always. But, you know, I like things that have forever. What's the best fashion brand that's not one of the ones you've worked for? Which doesn't leave many by process of elimination. I'll tell you who I say the best fashion brand is T.J. Max.

Oh. You know, what? It's worth $60 billion. They have real prices. And if you look at our industry today, I always say don't give them the credit card when you're buying something. Go online first to see where I can buy it for less. Best business book you've ever read. You know, I just finished Phil Knight's book 10 years too late.

Shudad, great book. I'm not a big reader, but I like that. I like to stick the detail. What's the best restaurant in New York City? I have none best. I don't have the best. Best restaurant in the Bronx? Well, it's probably an Arthur Aapner, but I don't go there anymore.

What about the restaurant where you control the playlist? Oh, San Ambrose. Oh, lovely. I like that. Prenchy Pacea Cake. Yeah, you know, that's... Best business leader you admire. Well, I love Steve.

Steve the best. And he was quirky and difficult. But he cared about the products that was first and foremost in every board meeting. He'd cover it with a gray cloth. and then he'd make the presentation. Wow. And he was, and look what he's done. I miss him.

We miss him too. And if you, Mickey Drexler, we're a stock and we're going to IPO, you personally, what would be your three or four letter ticker symbol on the stock market? That's a hard one. You know, Shoe, I think we should tell everyone to drink every time he says simple. So maybe SMPL. Yeah, SMP. Cote?

Cote works too. Yeah. Or Hamisha. That's too long. And finally, Mickey, before any guest leaves, we always ask them to whip up the takeaway. So what's the takeaway on Mickey Drexler, an American fashion? I never had a grand plan to be who I am today. In fact, when I'm objective, I'm quite anxious about keeping.

it up. So every day I have to beat myself and what I did yesterday. So the takeaway is it ain't easy to do this and be true to the business and yourself. And a lot of angst goes with what I am and what I do. But make today the best one yet. Oh yeah. Like every day I want to beat myself, not beat, but every day I need to do better than I did yesterday. Every day. And And I explain that to people. Well, Mickey, as a profound micromanager, we've agreed to hand over this recording to you so you can pick it apart and choose the parts that you prefer. Oh, really? Is that what you do? Thank you, Mickey.