The Monday Media Diet with Mickey Drexler

On the garment district, the art of merchandising, and an inspiring Paris Bar

We’ve long admired Mickey Drexler (MD) for being a businessman that can read the tea leaves of culture. He’s built and/or overseen some pretty iconic brands: Gap, Old Navy, as well as JCrew and Madewell. What I also respect is his astute read of when trends are beginning to crest, and knowing how to ride them, as evidenced by the Liquor Store + Ludlow jacket + Michelle Obama-era period at JCrew. He’s also a masterful merchant: read our pal Nick Paumgarten’s essential New Yorker piece on him to understand what this means. Some of the WITI crew (Reilly, Sam, Noah) have gotten to know him recently and he’s a wonderful raconteur and a super curious person. We’re very much excited to have him on the page and share his positive sentiments toward the French series, Le Bureau. Have a great week. -Colin (CJN) 

Tell us about yourself.

I grew up in the Bronx as an only child - my dad was a piece goods and button buyer in the garment district, and my mom worked as a secretary at the YMHA until she passed away when I was in high school. 

I believe that my ambition and drive was from a few factors stemming from growing up with a dad who wanted to be successful but never was - along with the environment I grew up in, for example a tiny apartment where I slept in the living room. I would probably also connect my career, either by genetics or experience, to my father's as he worked in the garment district and growing up I worked in the shipping department at the coat manufacturer where he worked on Saturdays and Holidays. 

A turning point in my life came when I was fortunate enough to get into The Bronx High School of Science which actually gave me a different outlook on life in terms of being in school with very smart kids -- I never liked being there because it was so fiercely competitive with many kids who always seemed to get better grades than me. I’m thankful to have gone there because it became a non issue regarding going to college, which was not a family value of my family and extended family.  

Aside from having great jobs, I also had the good fortune to be on the board of Apple for 16 years - I so loved Steve Jobs and admired him - it was a once in a lifetime experience to be a board member of Steve’s, along with being his friend. 

For the last few years I've been a major investor and advisor at Alex Mill-- a brand my son Alex started in 2012. To this day, I'm as involved in the same intense and detailed manner that I have been over the last 40 years of my running companies. I’m known to be a notorious kibitzer and schmoozer. Definitely one of my hobbies. 

Describe your media diet. 

I read a lot, but I don’t have a huge attention span, so I don’t read just one thing consistently. I don’t read many books. I mostly read newspapers, and all media that would be connected to our world of garments at Alex Mill, along with many other businesses in the retail and fashion world. I like to read about people and gossip, and real estate, which is a passion of mine. 

I am addicted to true life crime and mystery shows and movies on AppleTV, along with 48 Hours and Dateline. 

But most importantly I read everything my wife, Dr. Peggy Drexler writes, plus watching her documentaries, her latest being The Fight, which is a David and Goliath story about the ACLU and some of the cases during the Trump administration. Also My Name is Pauli Murray which is about a civil social rights activist. 

What are you reading (or watching) now?

The Bureau, a French series on Amazon Prime. And I recently started reading a new book- Disloyal by Michael Cohen, a story about him as Donald Trump's one time lawyer. 

What’s your reading strategy when you pick up a print copy of your favorite publication?

I highlight the articles of what I might be interested in or save them, mostly when reading the newspaper- I like the Wall Street Journal, particularly the Mansion and Off Duty sections. 

Who/what should everyone be reading or watching that they’re not?

The Bureau and the Fran Lebowitz Special on Netflix, Pretend it’s a City. 

What is the best non-famous app you love on your phone? 


Plane or train?


What is one place everyone should visit? 

The David Sheldrick Wildlife Trust in Kenya a home for orphaned elephants. 

Tell us the story of a rabbit hole you fell deep into. 

The reason Old Navy is in business today is because of an article I read on page 3 of the New York Times Business Section 26 years ago, about Target starting a brand called EveryDay Hero. It was supposed to be a less expensive version of The Gap according to the story - so the rabbit hole began. 

I flew to Mall of America to look at the store as soon as it opened - I walked through for maybe two minutes - that’s basically all it takes in my opinion to get a sense of a store environment, merchandise, etc, etc. I thought it was a very poor version of The Gap. BUT I started to think a lot about it.

On the way back to San Francisco, I stopped in Chicago for about an hour looking at two of our Gap stores that had lots of sales and were not in what I considered good Gap locations. Spoke to the teams and they said the reason they sell a lot on sale is that Gaps prices were too high for them. It blew me away as I thought Gap was always fair and moderately priced with good value - but everything is relative. 

My obsession continued - I did some research and found that 80% of the jeans in America sold for less than $30, and Gap's price point started at $34.50 (26 years ago). My last bit of research - I gave 10 selected Gap associates $200 each and asked them to shop discount stores including Target, Kmart-Sears, Ross Stores, WalMart. etc. etc. I assigned them each a category and met a week later to go through their findings and experience. By the end of the meeting, I had a strong instinct about starting a new company. They had said everything I hoped they would in terms of what they were looking for, nice merchandise, good value, service, and respect. None of them mentioned the store environment. but I was thinking it had to be a very exciting and cool environment, but that was always a given for me. 

One of the most difficult things is to name a new company. In Madewell's case, a company which I also founded, I purchased the name from a defunct workwear company in Bedford, Massachusetts. I sold it to J. Crew when we started Madewell a few years later. 

During this process, I was visiting a few cities in Europe as I usually did for inspiration, etc. I was in Paris on my way to the airport and  passed a bar on Saint Germain (now closed). The bar's name was Old Navy. 

Thanks for reading,

Noah (NRB) & Colin (CJN) & Mickey (MD)

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