Stuart Weitzman on the power of creativity, luck and risk

Image courtesy of Makenna Brown ’28.

Unlike most boys growing up in America during the mid-20th century, Stuart Weitzman did not play catch with his dad. Weitzman was not swinging a bat around in his backyard, either. He did, however, have a creative hobby that Seymour Weitzman, his father and shoe factory owner, gave a thumbs up: drawing. “It was the Jon Gnagy drawing course… It was a course that taught you how to draw real things, and then the next chapter in the book was how to draw non-realistic things, to use your imagination. And that was great. It became my hobby,” Weitzman recalled in an interview with The Miscellany News.

Weitzman, the founder of the world-renowned shoe brand that shares his name, spoke about this connection with creativity and his entrepreneurial journey in a lecture at Vassar on Sept. 25. The event was co-sponsored by the Center for Career Education, Contrast Magazine, Vassar Business Club and the Vassar Innovation and Entrepreneurship program.

Founded in 1986, Stuart Weitzman—both the brand and founder—had a distinct, clear goal from the start: “I wanted to make the opening price point of footwear in a high-quality setting. So if you went into Bergdorf Goodman, our shoes would be right next to [Christian] Louboutin, or Manolo Blahnik, or Jimmy Choo or Prada. I never wanted to be the most expensive on the lower price floor. I wanted to be the opening price point on the designer floor, because it carries [an] image for you,” Weitzman told The Miscellany News.

An understandable, logical goal. The question, or perhaps challenge, was: How would Weitzman pull this plan off? The answer: celebrities. Standing at the front of the Villard Room with a grin on his face, Weitzman explained to the crowd that he has always had muses. Marilyn Monroe. Audrey Hepburn. Women who occupied one end or the other on the spectrum of glamour to subtlety, of innovation to timelessness. 

“I needed a niche to make me stand out. On the red carpet, I noticed every actress had a different dress, but everyone had the same shoes. Everyone was making custom dresses, but no one was making custom shoes. I thought, wow, if I could do in footwear what people are doing in dresswear, maybe that could be my entrance into fashion,” Weitzman explained to the Vassar students who had come to see him speak. 

One red carpet in particular turned Weitzman’s idea into reality. It was 1983 at the American Music Awards (AMAs), and one of the greatest muses of all—the “Queen of Soul” herself, Aretha Franklin—took off her shoes when accepting the award for “Favorite Soul/R&B Album” for her 28th studio album, “Jump to It.” In her left hand, she held the crystalline AMA award up. In her right, Franklin held her shoes up, a pair of Stuart Weitzman for Mr. Seymour—Weitzman’s father’s company—d’Orsay pumps.

“Aretha Franklin took off her shoes, and not only showed them to the audience, but also to 30 million people. And she said, ‘I would like to thank Stuart Weitzman because these shoes are so comfortable and so beautiful.’” This moment, Weitzman explained to a wide-eyed audience, forged the path for the brand to become known as the shoemaker for the stars. “It was luck, but it wasn’t luck,” Weitzman exclaimed.

This mantra about luck applies to facets of Weitzman’s journey beyond his brand’s relationship to celebrities. Luck but not luck—this is how Weitzman determined the manufacturing location for his brand: Elda, Spain. When deciding where to manufacture his shoes, Weitzman planned tours in both Spain and Italy. 

“I got to Italy, they had a four-hour strike at the airport. We couldn’t get our luggage. The next day, hotels had a four-hour strike. Then, the shoe factory I was supposed to see that was recommended, he was closed in the morning for a strike,” Weitzman recounted to The Miscellany News with a laugh. “Next day, I fly to Spain to visit factories. My plane was delayed, and I got there [at] 10 of one. Well, in Spain, they have a siesta, and they’re closed from 1 p.m. to 3:30… I spoke to the owner, I said, ‘I have to catch a plane tonight at 6 o’clock. Can’t you keep it open and we’ll go to siesta, maybe four?” 

The owner’s response? To Weitzman’s surprise, a gleeful, “Yeah, sure!” Luck, persistence and compromise—this balance has provided Weitzman with silver linings and unlikely success throughout the years.

When luck and compromise are not enough, one four-letter word motivates both Weitzman and his business decisions: risk. Risk is a core pillar of what Weitzman calls the “truisms” of business, entrepreneurial and creative advice that Weitzman asserts are universally true. Weitzman himself took one of the biggest risks of his life when he was the same age as many of the Vassar students that comprised the lecture’s audience. When he was a student at the Wharton School for Business at the University of Pennsylvania (Penn), Weitzman had a job lined up postgrad to go to Wall Street and work for the investment banking company Goldman Sachs. This plan was all despite the fact that Weitzman, from his childhood drawing with the help of the Jon Gnagy course up until his time at Penn, had loved both sketching and shoes. 

But just as he was about to go off into the world of investment banking, a classmate introduced Weitzman to his father, a freelance shoemaker who was in a creative rut. Weitzman sketched 20 shoe designs, one of which was torn up by the shoemaker who did not believe Weitzman had created the sketch; Weitzman was asked to recreate his original drawing and, to the shoemaker’s surprise, he did. The man paid Weitzman $20 for each of the designs he produced. This fast-paced decision that rewarded artistic expression shifted Weitzman’s thinking about Wall Street. “It [Wall Street] would be so boring compared to the life I’ve led. The fashion industry is so much fun.” 

Weitzman cited other “truisms” for his success too, including imagination, inspiration and the fact that it is impossible to be successful without the help of others. All of these may not be possible, however, without taking that initial risk. “Sometimes people are doing things in school that they feel they have to and they’re not going to have a happy career.” Stability is exceedingly tempting. But betting on yourself—betting on risk itself—can be promising too. Weitzman continued, “You want your heart to sing when you’re doing something after university or college. That’s what you need. And if it doesn’t make your heart sing, go find the tune somewhere else, because that’s what you need.”

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