Designer Stuart Weitzman discusses balancing creativity and business

Weitzman, founder of the iconic shoe brand Stuart Weitzman Shoes, visited Yale as a featured speaker in the Yale INSPIRE Series.
Shua Hahm
Contributing Reporter

Shua Hahm, Contributing Photographer
Stuart Weitzman, founder of high-end shoe brand Stuart Weitzman Shoes, spoke to the Yale community at the Tsai Center for Innovative Thinking on Monday evening.
The event was part of the Yale INSPIRE Series, a series of talks with esteemed entrepreneurs and founders from varying backgrounds open to all Yale students. Weitzman, whose shoes have graced the feet of global icons from Beyoncé and Kate Middleton to Taylor Swift, spoke about his passion for designing and his road to a founder, entrepreneur and creative director.
“Pay attention to the road less traveled, so much of what I’m going to tell you is not traditional, but boy did it work,” Weitzman said.
Weitzman spoke about the importance of trial and error, advising the audience, many of whom were undergraduates, to learn by doing, instead of in an academic setting. He emphasized that experience in the real world itself is vital, and in his mind, the better alternative than returning to school after college.
He then shifted the talk to the time he spent working for another shoe company after graduating from The Wharton School of Business at the University of Pennsylvania, which he credits gaining much of his business expertise from.
“Before you do your life’s work, work somewhere else first,” he said. “If you do work somewhere else first, you will gain experience that is invaluable. We made a lot of mistakes, and I never paid for any of them.”
Weitzman then transitioned to speaking about the core traits he believes are essential to any entrepreneur, adding numerous anecdotes for each one. He referred to these traits as “truisms.” Weitzman’s business partner, Barbara Kreger, who was also in attendance, shot up and said to the audience and shouted, “or what we called Stu-isms.”
His first “Stu-isms” was about risk: the importance of taking them and how they had shaped his journey and his company.
“It’s like buying a lottery ticket, if you don’t buy it, there’s no chance you’re going to win the lottery ticket”
Weitzman said that when he first started making designer shoes, a custom shoe market was not in existence. He had an idea to enter the custom shoe market through award shows — thinking along the same vein of how celebrities wore custom dresses — and took his first big risk by calling a stylist he knew from a previous job, asking if he could create said custom shoes for any celebrity.
The celebrity happened to be Aretha Franklin, who showed off his shoes to the world while receiving her American Music Award in 1983, launching Stuart Weitzman’s name into a global fashion.
“Within two months, there wasn’t a stylist in Hollywood that didn’t call to make shoes for their A-list celebrities … and we hadn’t yet even put our shoes in stores you would recognize.”
In an interview with the News prior to the event, Weitzman discussed various life lessons he learned throughout his career, from the real secrets he learned in school and how he decides what charities to support, to what inspiration looks like for him.
Weitzman said that his most important value was imagination and urged people to keep hold of it, even as one grew older. When asked how he would introduce himself, Weitzman spoke solely on his personal life, omitting all mentions of his career.
He spoke on his current values in life, and how he had made it a mission to spend time with his daughters. Outside of this, he emphasized his love for tennis and ping pong.
After the event, Miffy Wang ’28, also an artist, discussed what it meant to hear from someone who had succeeded in the industry, emphasizing his ability to blend creativity into his business model.
Samantha Kuo SOM ’26 spoke to the News, emphasizing Weitzman’s approachability.
“I own thirty pairs of Stuart Weitzmans,” she said, “So it’s really cool to finally see this mysterious man. Sometimes there can be barriers to understanding these really well known and high profile people, but with him, it’s like your grandpa telling stories before bedtime.”
The TSAI City building located on 17 Prospect St. opened in 2020.
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