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Stuart Weitzman: Building a Shoe Brand Meant Taking the Road Less Traveled

Fashion mogul and entrepreneur started making a name on the red carpet, but his journey led him to even larger realms of success

Stuart Weitzman is best known for the designer footwear that carries his name, shoes as distinctive and beloved as glamorous stilettos, gladiator-inspired sandals, and chic espadrilles. Celebrities such as Beyoncé, Kate Middleton, Meghan Markle, Taylor Swift, and Jennifer Lopez have helped propel his brand to the upper realms of luxury shoe design. 

Having recently sold his company, the former CEO and creative director of the Stuart Weitzman business shared lessons from his career with aspiring entrepreneurs at Tufts on February 22. His presentation, “An Entrepreneur’s Journey on the Road Less Travelled with Stuart Weitzman,” was co-sponsored by the School of the Museum of Fine Arts and the Derby Entrepreneurship Center. 

The title, Weitzman explained, is an homage to his “mantra,” taken from the closing lines of Robert Frost’s poem "The Road Not Taken," which ends, “Two roads diverged in a wood, and I—/I took the one less traveled by,/And that has made all the difference.” Weitzman encouraged his listeners to take unusual paths rather than expected routes.

“When you do something … [if] you don't want to take the straight line, figure out a way to get there roundabout,” he told a rapt audience of Tufts students. “You'll have more fun. You will be noticed in a greater way.”

Below are a few selections from Weitzman’s many experiences as he walked the path “less traveled by.”

On Risk

Weitzman recognized early on the priceless value of risk in an industry “cluttered with too many brands, too much product. I needed to find a niche,” he said. 

That niche, it turns out, began by noticing that, at red-carpet galas, “every dress was different, but many shoes were the same.” While designers were making custom dresses for celebrities, “nobody was making them custom shoes.”

“Wow. If I could make a shoe exclusively for these wonderful ladies, maybe just maybe, I’ll find my niche and get noticed very quickly and not take a half a dozen years for me to get recognized,” Weitzman recalled thinking. “So I took this risk.” 

The risk: gambling a third of the money he’d earmarked for a major business by investing it in “a little shoe factory that would make one-of-a-kind shoes. … And nobody is even going to pay for the shoes I’m making,” he said. “That is not good business sense, but it is good savvy sense if I'm going to create a niche.”

Weitzman reached out to celebrity stylists he had never met, and the one who called him back was signed on by Aretha Franklin for the Grammys. As luck would have it, Franklin won a Grammy wearing Weitzman’s stylish custom shoes. “She thanked her mother and her songwriter, her agent and all that,” said Weitzman, “and she takes off her shoes, shoves them into the camera and said, ‘and I want to thank Stuart Weitzman for making me these beautiful and oh-so-comfortable shoes.’”

“It was really luck that she won it,” he said. “But if you're not out there playing the game, how can you ever get lucky, right? If you don't buy a lottery ticket, is there a chance you could ever win the lottery? Of course not. We bought the lottery ticket.”

On Imagination

Weitzman illustrated the power of imagination as he described his path to reaching broad public awareness. He wanted people “to know Stuart Weitzman, the brand, not Stuart Weitzman the shoe necessarily, yet”; his aim was “to advertise our brand and our DNA and how well we love this product.”

Chelsie Wei A24, models diamond-encrusted sandals, a design idea actress Laura Harring debuted at the Academy Awards. Weitzman followed up by inviting retailers in Europe, Australia, and in Asia to see the "million-dollar sandal" during fashion week in Milan and Paris, and orders were soon pouring in. "That shoe opened that entire market for me," said Weitzman. Photo: Glenn Kulbako Photography

The full page magazine that resulted honed in on the DNA with striking simplicity: a single photo of “Stuart’s dog”—a Dalmatian whose “spots” were black heels and the tag line “a little obsessed with shoes.” The ad won the first Cleo Award for print advertising and was wildly popular as a stand-alone design, Weitzman said. He received thousands of requests from mothers for a poster of the ad to give their young daughters. 

“I made 8,000 posters and I sent them out to these ladies and those kids were, maybe 10, right? [But] 11 or 12, 10 years later, how old were they? And what brand had they known all during their teenage years? Stuart Weitzman,” he said. “And I think that's how we started to get the bride and many other customers because this ad had more legs than I thought it had.”

On Inspiration

Muses are everywhere, you just need to know where to look, according to Weitzman. Take the popular Teva sandal. One season, “they put the ankle strap on it and then the young girls were buying it like crazy,” he said. He was inspired to make the gladiator sandal. 

“The last time I had seen a gladiator sandal was on a statue in Rome on somebody 2000 years old,” he said.

What elevated his sandals into the hearts and minds of the wider public was Weitzman putting them on supermodel Kate Moss. “We put it out in the right places,” he said, adding that the sandal went on to enjoy three spring seasons. “That's how successful it was.” 

The lesson, he said, is to “keep your eyes open, always for inspiration, wherever it might be, and not necessarily on the road that's always traveled, but more on the road that isn't traveled.” 

On Why You Can’t Do It Alone

Weitzman’s success was not due to his ideas and drive alone. In several instances, he advanced the brand by making connections with famous people. 

He wanted, first and foremost, to be where they bought their shoes. That paid off with Jennifer Aniston falling in love with his espadrille and Kate Middleton with his five-inch platform wedges. “You can’t send shoes to people like this,” he said. “You can’t ask them to endorse you. You have to find out where they buy their shoes. … You have to think about how people can help you improve, not just your life, but your career, your work, your business. You can’t do it alone.”

Similarly, when he wanted to open a store in the fabled IFC Mall in Hong Kong and was rebuffed by the mall manager, he set about designing a store with the “queen of architecture,” Zaha Hadid. “If she will design a store for me, I thought maybe that will open the market, not because of my shoes, but because of Zaha,” he said. The Milan boutique, featuring sinuous display shelves, opened the week before Fashion Week, and the manager of the IFC Mall, “like anyone else in his world, has to come to fashion week,” said Weitzman. The manager was impressed by the boutique, as Weitzman had hoped, and offered him “the best location” for a Hong Kong store. 

Weitzman's words of advice: “You have to research what will motivate. I had to think about: What is the answer? What's the other way? Because … I couldn't get through his door. I couldn't get in IFC until Zaha built me a store that interested this guy. That was a very, very great lesson for me.”

On Community

The arc of Weitzman’s career would not be complete without his commitment to wider causes. “When you're successful, I want you to bear this in mind: try to be part of the community,” he said.

One of the causes he chose to support was the Susan G. Komen breast cancer research foundation. He did so first by enlisting the support of actresses. He sent them each a single white satin high heel pump and asked them to “decorate it, cut it up, add something.” Then the shoes were sold at auction. “The first season we collected $300,000 from 25 works of art by actresses,” he said. “The next year we did men. The year after that we did musicians and finally athletes.” In total, the “designed shoe” campaign raised $1.3 million. 

The rewards of thinking about community, said Weitzman, go well beyond the dollar amount. “The charity got something unexpected. The actresses and actors had great fun creating something. So many said to me, ‘How much did my shoe go for?’ They were proud. Our company had such great press from it. We had so much fun doing it. And the public, they got a work of art. Maybe the only one that Oprah ever made,” he said. He suggested that people look for creative ways to give back. “You don't just have to think about writing a check but do be part of the community,” he said. “The pleasure you get: incredible.”