Beginning From a Sketch
World-renowned shoe designer Stuart Weitzman recently visited the Fairfield University Quick Center, sharing insights on creativity, entrepreneurship and the power of imagination. The event was presented in collaboration with the Dolan School of Business Fashion Marketing Program and WSHU, an NPR radio station owned by Sacred Heart University. It highlighted Weitzman’s inspiring journey from a young apprentice to an industry icon.
Weitzman’s career began in his father’s Massachusetts shoe factory, where he worked during high school. His first design, a sketch he submitted to his father, marked the beginning of a lifelong passion. By 1986, he had launched his eponymous shoe brand, quickly gaining a reputation as one of a few designers who was also a patterner. His philosophy was clear: “A beautiful shoe is useless unless it feels as wonderful as it looks.”
Though he retired in 2017, Weitzman remains deeply involved in visiting colleges and universities to share his experiences.
Entrepreneurship
Weitzman emphasized the importance of building a career on a solid foundation. He advised students to work somewhere else first, whether through graduate school or gaining industry experience, spending five to six years learning from the best before venturing out independently. He credited his success to the years he spent meeting suppliers, learning from industry experts, and understanding business before launching his own brand. He said, “I learned over time, not through textbooks, the truisms and nuances of entrepreneurship.”
He outlined several core truisms of his:
- Risk: Describing risk as “your best friend,” Weitzman stressed its necessity. He drew parallels to icons like Andy Warhol, highlighting how his 1964 Pop Art portrait of Marilyn Monroe, “Shot Sage Blue Marilyn,” sold for $195 million. He advised, “Weigh what will the benefit be and will I afford the loss.”
- Imagination: To stand out, Weitzman relied on bold creativity. Inspired by haute couture, he sought to make shoes as exquisite as Valentino dresses. His daring advertising campaigns – such as the infamous ad featuring a Dalmatian with heeled shoes for spots or the Halloween ad in Vogue magazine with a bulky fold-out insert – became legendary. In fact, 91% of people referred to the Halloween ad two months later when asked about recent fashion ads.
- Inspiration: Weitzman drew from art, music and pop culture, looking beyond the fashion world for ideas. The thigh-high boots Julia Roberts wore in “Pretty Woman” became an iconic fashion statement. His custom thigh-high boots for Taylor Swift’s “1989” tour sparked 800,000 customers for the $1,000 boot. He explained that, “Some places can be dead ends. Some places can be four-lane highways.”
- You Can’t Do It Alone: Weitzman stressed the importance of collaboration. When he wanted Jennifer Aniston to wear his shoes, he discovered she only shopped at Scoop in Los Angeles and did not typically do shoe ads. Instead of giving up, he tracked down the boutique, persuaded them to carry four of his styles, and soon after, Aniston bought and fell in love with his espadrilles.
- Solve a Problem: Problem-solving was at the heart of his business strategy. When thirty percent of celebrities changed their outfits last-minute on the red carpet, leaving his shoes unused, Weitzman created a versatile shoe that could be dyed any color– gold, white satin and metallic silver and gold. This practical innovation made the shoe a red-carpet staple for over a decade.
- The Tipping Point: Weitzman understood the power of perception and publicity. To generate buzz, his company created “the most expensive shoe ever made” – a million-dollar sandal adorned with 464 diamonds and a 14-karat teardrop diamond dangling from the center. The extravagant design made headlines and proved that creating a memorable moment could drive global attention.
- Repetition – Repeating a product or idea in different contexts can lead to massive success. Weitzman described how Kendall Jenner’s thigh-high boots and Cara Delevingne’s platform version of his shoe became media sensations. When Delevingne was voted best dressed of the night, Weitzman’s shoes became a lottery-winning success, selling out rapidly.
- Perception: The Cinderella shoe Weitzman created from plexiglass was initially dismissed as inferior to leather. He shelved the design for fifteen years. When Broadway’s Rodgers + Hammerstein’s Cinderella debuted, he re-released the shoe – this time pricing it $65 higher than a leather shoe. “It was no longer a plastic shoe; it was a novelty shoe,” he explained, illustrating the power of perception.
Timeless Advice
To the students, Weitzman offered parting words of wisdom: “I hope they find something they absolutely love. They have to love it. If it makes your heart sing, you will be better at it than the next person.”
When hiring, he revealed that he prioritized hiring “nice, smart and communicative” people, never putting experience on the top of the list. This is an encouraging reminder for students who may feel anxious about job interviews or lack of extensive experience.
With millions of pairs sold worldwide, Stuart Weitzman’s legacy continues to shape the fashion industry – one remarkable step at a time.



















