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Stuart Weitzman almost went into investment banking — and then he didn’t

Only Kate Middleton can play volleyball in skinny jeans and heels — and execute it flawlessly, as demonstrated by a fan edit on my For You Page. The unsung hero, though, was her trusty pair of navy suede Stuart Weitzman Corkswoon sandals, a pair that, apparently, warrants an entire slideshow on the Kate Middleton Style Blog. The slideshow proves that the wedges are sporty enough for volleyball; but also ergonomic enough for some casual shoveling; but also diplomatic enough for charity engagements.

This aspect of feminine functionality has differentiated Stuart Weitzman’s women’s footwear designs in an industry where shoes are more often designed for the starry-eyed male gaze than for actual practicality. At the core of Weitzman’s designs and his entrepreneurial experiences is a genuine understanding of the customer and perhaps more broadly, the human. Whether through his long-established friendships with his celebrity clients (I asked Weitzman who his favorite Kardashian was, to which he said, “I think Gigi Hadid is great!”) or his emphasis on practicality in the shoe design process or his philanthropic efforts supporting Jewish communities, his entrepreneurial successes are in large part because he is willing to listen to — and learn from — the people who buy his shoes. 

Most recently, Weitzman led a seminar hosted by Duke’s Career Center, Duke Innovation and Entrepreneurship and Jewish Life at Duke. The Chronicle sat down with Weitzman to talk about not going into investment banking, his Jewish heritage and how he came to understand his consumer. 

This conversation has been edited for length and clarity.

TC: Duke has this really intense professional culture where everyone feels this pressure to go into investment banking or consulting. I know you went to Wharton and almost went into investment banking. Ultimately, you chose design. What led you to follow your own path?

SW: My hobby was always drawing and making things. I used to do the artwork for Penn’s Mask & Wig, an all-guys musical group, and I helped dress them up for shows. One day, I thought, I gotta do the whole thing. 

Can I have a piece of paper? 

TC: Sure. 

SW: I was going to go to work at Goldman Sachs. I had interned and I was offered an opportunity to start there after college. But this fella of mine asked me to design shoes for his father, a shoemaker. So he brought me his father’s catalog, and I drew 20 sketches and went over to their house for dinner. The old man — Eastern European, gruff guy, hands callused — laid out my sketches like a deck of cards, fanned them out, and picked one up.

Weitzman, imitating his friend’s father, squints at the piece of paper with an eyeful of doubt.

SW: He told me, “I don’t put anything in my collection that’s copied from somewhere else. So I want to know who you copied this from.” I said, “I didn’t, sir. I looked at your catalog and drew what I thought would work with your customer.” And he put my paper up to the light and said, “I see sketch marks. It looks like you traced it.” “I didn’t, but I didn’t come here to sell you anything. It was your son’s idea.”

Weitzman shreds the paper with an authoritative grip. 

SW: Then he just rips it up. About 15 seconds went by, and I’m just sitting there, not knowing what to say. He picked up another sketch, and asked me to sketch it on the spot. So I did, and he told me, “I’ll give you 20 bucks per sketch.” That was $380 — at a time when Penn’s tuition was $1500 a semester. I had made $380 in an hour, and I thought, maybe I should try this.

TC: The most shocking part is how cheap your tuition was. But wow, that must have been so validating.

SW: It was. I called up Goldman Sachs and put it off for a year. Then I saw one of my sketches in the window of a Bergdorf Goodman — and then the store told me they sold that shoe out. That was exciting. So I gave up finance, but I will tell you that the experience at Wharton was tremendously helpful to me in building a business where I was both the CEO and the creative director.

TC: What kind of advice would you give to someone who’s in a similar boat… someone trying to decide whether to be a corporate sellout or to follow their lifelong dream? 

SW: If you have a passion for something, try to do it non-corporately — either with a smaller business, or eventually on your own. I would advise the smaller route: better opportunity, less competition. The finance and tech world is where everyone wants to go, because they’re driven by money. You shouldn’t necessarily take the job that pays you the most. Take the job that thrills you the most. 

TC: What kinds of lessons did you learn from college, even if what you studied wasn’t directly related to designing shoes? 

SW: The best thing I got out of college was great friendships. My college friends are still my best friends. Penn is like my third child.

TC: You talk a lot about supporting the Jewish community and honoring your heritage. Why is that important to you? 

SW: Heritage is so important — we are all Americans, but we are all something else. I come from a Jewish heritage, but I’m not a religious person at all. But it’s a culture, a heritage that I’m so proud of when I see people like Pfizer CEO Albert Bourla, whose parents survived the Holocaust and who helped create the Pfizer COVID-19 vaccine. They survived, and look what he accomplished. 

TC: One of the things that distinguish your brand from so many other womens’ footwear brands is that rather than appealing to the male gaze, you really listened to the woman consumer. So how did you come to understand that perspective?

SW: I’m making shoes for women. What the heck do men know? We had 73 managers and up at my company when I sold it, and 71 were women. That wasn’t by accident. The biggest change in our company occurred when I created our thigh-high boots. And that came about when a young lady, college-aged, told me, “I know you, my mother wears your shoes.” I thought then that I needed to go after these younger generations. Because that became the new market. So that really shook me up to go after a change like that. 

TC: Is my generation hard to understand? How has it been catering to us?

SW: Terrific. They’re the ones who get excited about the product. They see it, they want it. It adds to the thrill of fashion. Our DNA is comfort — fashionable shoes that are comfortable. Louboutin makes gorgeous sexy shoes that kill the feet. We put comfort and fashion together and decided that fashionable shoes don’t have to kill your feet.

TC: Did you ever have to make any compromises working in fashion? 

SW: Even if a shoe was gorgeous, if it didn’t work, we didn’t make it. You put on a shoe, it gives you a blister, you’re not going to come back to my store. Our most famous sandal — the Nudist — changed Hollywood. I drew it in one afternoon. Wasn’t approved for two months. 19 different trials until it finally worked. And when we put it in the marketplace, it did fabulously. 

TC: How is retired life?

SW: I love it. I’m with my kids a zillion times a month. I’m speaking at 19 different colleges this semester. So I’m still busy. I got back into all the sports I loved as a kid. I’m at a ping pong table every day. I’m not having any trouble filling the days. 


Derek Deng | Recess Editor

Derek Deng is a Trinity senior and a recess editor of The Chronicle's 119th volume. 

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