When Stuart Weitzman asks you what shoe size you wear, I now know the correct answer is “what size do you need me to be?” 

Unfortunately, that was not the answer I gave on the evening of March 17, when luxury footwear designer Stuart Weitzman spoke at Wake Forest University’s School of Business. As a result, another lucky girl got to slip her size-nine feet into Weitzman’s infamous million-dollar-diamond-encrusted sandals, first worn by actress Laura Harring at the 2002 Oscars.

Weitzman’s talk was equal parts inspiring and humorous. He incorporated engaging anecdotes to tell the story of his path to success. 

Weitzman’s father introduced him to shoemaking at a young age, putting him to work at the family shoe company, Mr. Seymour, in Haverhill, Mass. As a young adult, he pursued business at the Wharton School at the University of Pennsylvania, where he also drew and painted as a pastime. 

“My creativity was a hobby,” Weitzman remembers. “I didn’t plan for it to be a business… that just serendipitously happened.” 

One of Weitzman’s peers admired his sketches and asked him to draw shoes. He drew 20 shoes, the most iconic of which was a pump with alternating snake and leather print. Over Easter break, as Weitzman was walking down Fifth Avenue, he spotted one of his designs on display in the window of an I. Miller shoe store, America’s premier shoe company at the time.

He ran inside to inquire about the shoe. The salesman told him that the store had sold out and was on back order. Because his name wasn’t attached to the design, Weitzman described the moment as akin to what he imagined Taylor Swift felt when she first heard one of her songs on the radio before she was famous. 

“It had to drive her nuts,” he said. “She was so upset. That’s how I felt.”

After college, Weitzman continued to work at his father’s company, then recruited three peers to help him establish his own brand. Unusually, Weitzman maintained both the roles of CEO and creative director of the company.

Weitzman’s shoes have since become a staple of luxury footwear, often seen on the feet of Jennifer Aniston, Jill Biden, Gigi Hadid, Kate Middleton and Taylor Swift. Taylor Swift was so taken by his thigh-high boots—which were inspired by popular media like the 1990s film, Pretty Woman—that they became her constant companion during her 1989 World Tour. 

“I need to be inspired,” Weitzman said. “I have yet to hear about a designer who can sit in a little room, make his collection and go home. If there is one, I’m positive that his shoes don’t sell.” 

Weitzman’s background in business manifested in his savvy manipulation of the market and granted him a world-renowned reputation in the shoe business.

For example, he launched an ad campaign called “A Little Obsessed with Shoes” in 2002, which featured a Dalmatian with black shoes in place of black spots. The image was so popular that he received numerous requests to produce a larger version for house decor. Weitzman decided to eat the production price of manufacturing the posters in hopes that it would pay itself forward. 10 years later, Weitzman said, his company made strides in the bridal market, which he attributes to women seeing the ad when they were young girls.

In 2013, Stuart Weitzman made the expert decision to task photographer Mario Testino to create an ad for his new line of boots. Weitzman cleverly utilized Testino’s preexisting relationship with famed model Kate Moss to recruit her to be the face of the campaign. The result was a short film titled “Made For Walking” and produced as a favor by James Franco. What could have been a 10 million dollar production only cost Testino’s expertise and partnership. “You want the best. It will end up costing less.” Weitzman explains simply how a series of smart business decisions resulted in, as he described it, “an ad you can’t buy.” 

Weitzman said his legacy manifests itself in love letters and compliments. His favorite fan mail was written by a young woman whose yacht sank after a hurricane in the New Orleans Harbor. It reads: “Yesterday it was raised, and there was not much salvageable, except my twelve pairs of Stuart Weitzman shoes, which were preserved by your meticulous plastic wrapping.” 

Another moment Weitzman remembers feeling satisfied with his career was when a woman approached him at a party and said, “I can’t wear your new shoes. I don’t know what you’ve done. They don’t fit me. I just don’t like them. I don’t even like the designs. I like what you used to do.” 

He responded by saying, “Don’t blame me, I don’t own it anymore.” 

In 2015, Weitzman sold his company to Coach. It exchanged hands last year for $120.2 million and is currently under the purview of Caleres. Weitzman has shifted his focus to philanthropic and educational work in his retirement and plans to continue his speaking tour at other universities across the nation.   

“Do you secretly judge people on their shoes?” I asked Weitzman towards the end of our conversation.

Weitzman responded: “Like Forest Gump said, in the scene where he was waiting for the bus and trains his eyes on the shoes of a man passing, ‘my mama told me, you can tell a lot by a person’s shoes, where they’ve been and where they’re going.’ I think there’s a lot of truth in that.”