Sam Edelman’s Wild Ride: From Aspiring Actor to Footwear Design Legend

Hit maker, comeback king, showman. Sam Edelman has been called many things in his 40-plus-year career in the footwear business. Although, on this particular Thursday in late August, he’s proving to be especially tough to pin down.

Not only existentially — he’s known for his multifaceted wizardry as a salesman, marketer and designer — but because he’s late for a cover shoot in the midtown Manhattan showroom for his eponymous brand.

It turns out that his day is already well under way. The shoe legend arrives in a dark T-shirt with gym bag in tow.

Sam’s wife, muse and longtime business partner, Libby Edelman, characterizes him as the ultimate go-getter. “He’s definitely Type A — Type A+ even,” she told FN. And she ascribes much of his success over the years to his unusually diverse range of talents. “He’s a great thinker, designer; he’s a great forecaster and great at creative. He’s 360 degrees of what you need to run a business.”

As president of the brand he co-founded with Libby in 2004, Edelman, 67, is intimately involved in almost every aspect of the operation, from shaping the look of the spring ’20 collection to expanding the firm’s retail portfolio (which now includes 13 doors across the United States). Recently he even took over developing the concepts for its advertising campaigns, departing from the glossy poolside vistas of recent ads and, instead, returning to the brand’s whimsical and irreverent origins.

In fact, after Edelman gamely poses for a few portraits and sits down to talk about his life and career, our conversation is halted briefly when the new face of the brand — model Alicia Herbeth — pops by to prepare for a shoot the following week. Edelman greets her like a long-lost niece (he considers every member of the company to be like part of his family) and shares the vision for the campaign in upstate New York.

That knack for storytelling is at the heart of Sam Edelman’s tremendously successful formula. Team members note that each season, the brand’s design process involves creating a complex narrative around a fictional woman and her elaborately crafted lifestyle.

But few of Sam Edelman’s story lines are as fascinating or as unexpected as his own.

Sam Edelman - CEO Sam Edelman Shoes, Photographed in the Sam Edelman New York City showroom August 22nd 2019
Sam Edelman.
CREDIT: Brad Trent

Born in New York’s Greenwich Village in January 1952, Edelman came of age at the beginning of the city’s counterculture movement, attending progressive schools like The Little Red Schoolhouse, where at a young age he learned Italian and French (he is still proficient in the former and fluent in the latter) and fell in love with creative writing and acting. He then studied theater at Sarah Lawrence College in Bronxville, N.Y., where he aspired to become an actor.

That is, until he went to his first audition in New York and found himself among dozens of other boys. “I realized the competition to be an actor was so tough, and I was not a good dancer and I couldn’t sing,” said Edelman. “So the actor thing stopped that day.”

At the same time that he was pursuing his creative aspirations, Edelman also exhibited a flair for business, which he attributed in part to his father (“a professional actor and a brilliant salesman”) and his maternal grandfather, who both worked in the family’s leather company.

“My grandfather was a Russian trader who came to this country with nothing,” said Edelman. “He had a true business acumen and educated me in numbers when I was a little boy. Driving in the car, we would do multiplication, percentage, markup. I thought he was an amazing man and dreamt of having a custom-made suit from Saks Fifth Avenue like he wore.”

Edelman developed his first entrepreneurial scheme when he was 13 when his father bought him a bicycle from a store on 7th Avenue and 12th Street. “I went back to my room and dreamed about buying the store. I had ideas to enlarge it and fix bikes and make a profit. Buying and selling was interesting to me even then,” he said.

Later, in college, Edelman kept money in his pocket by trading in horses via ads in The New York Times. “I’m very proud of the fact that I never had to eat in the dormitory cafeteria,” he boasted.

That passion for horses led to his first fashion venture: Horseshoes, a line of English riding-inspired footwear that he launched with his father in 1975. The collection quickly garnered press attention and caught the eye of execs at Ralph Lauren.

“Stuart Kreisler, the president of womenswear at Ralph Lauren, called us and asked us to do the shoes for their fashion show. We did it, and then Ralph suggested we license the shoes,” recalled Edelman, adding that the partnership, though short-lived, cemented a lifelong friendship with Kreisler, who was the best man at Sam and Libby’s wedding and is godfather to one of their children.

And Edelman, at the time around 24, also soaked up many lessons from Lauren, whose star was already on the rise. “I was so impressed by him, not that he was Ralph Lauren because he wasn’t that big a deal yet, but he set a standard for excellence, a standard of style,” said Edelman.

Sam Edelman - CEO Sam Edelman Shoes, Photographed in the Sam Edelman New York City showroom August 22nd 2019
Sam Edelman.
CREDIT: Brad Trent

It was during these years that the young entrepreneur had a fateful encounter with a young editor from Seventeen magazine.

“We met in the June shoe show [in 1979] and then really fell in love in the August shoe show,” recalled Libby Edelman. “We got married in May of the next year, so it was a very fast courtship. But he’s a fast guy. When he makes a decision, it’s like, let’s see if we can get it done yesterday.”

Over the years, the Edelmans’ love affair has been well documented, not only in the press, but in ads for the brands they have created together. Theirs has been both a very public and very profitable union that has lasted four decades and produced two brands, three children and now three granddaughters.

“Libby is the balance to everything I do; she’s my muse,” said Sam. “Living up to her standards isn’t always easy, but in the end, my goal is always to live up to what she represents in the world.”

Their partnership has weathered many of life’s ups and downs, the first of which came quite soon after their marriage.

Around 1980, the Edelmans closed their footwear company, and Sam turned to friends for help with his job hunt. “I called Kenny Cole and said, ‘I’m newly married, I’m broke, I need a job. Can you put in a call for me?’” recalled Sam. “And in Kenny’s inimitable fashion, he said, ‘No. You’re only going to work with me if you’re in the shoe business.’ ”

So he headed to Candie’s to work with the Cole family, and then in 1982 joined his friend to help create Kenneth Cole Productions. Edelman describes the experience as one of the most exciting of his life: “Kenneth was a great influence on me because he believed he could do anything. He didn’t worry about financing or the outside world. He really is a man with no fear.”

Once the initial startup work was complete, though, Edelman began to crave a new challenge. That arrived in 1983, when Doug and Susie Tompkins lured him across country to San Francisco in order to launch shoes for their thriving Esprit label.

“We moved to California on April 1, and Libby said this could be the greatest April Fool’s joke or not,” he recalled.

It was not. As head of footwear, Edelman built it into a $55 million business, making Esprit the No. 1 junior’s shoe brand in America. He traveled the globe with Susie Tompkins and her design team, gaining exposure to rich cultural experiences and getting a master class in manufacturing.

Along the way, he linked up with Bob Goldman at Cels Enterprises. “The shoes I couldn’t make in Brazil, Bob made for me in Taiwan. I learned a tremendous amount about shoemaking from him, and we did a couple million pairs together,” said Edelman. “He’s still one of my best friends.”

The young Esprit executive also began sourcing footwear with Brown Shoe Co. in St. Louis, the company that decades later would become his corporate home. (Brown Shoe — now Caleres — began investing in his Sam Edelman label in 2007 and fully acquired it in 2010.)

Sam Edelman - CEO Sam Edelman Shoes, Photographed in the Sam Edelman New York City showroom August 22nd 2019
Sam Edelman, photographed for FN in his midtown Manhattan showroom.
CREDIT: Brad Trent

After four years with Esprit, Edelman faced another career turning point, this one not of his making. The Tompkins announced they were divorcing and turning over management of the company to a new executive, who had other plans for the footwear operation. “He interviewed my parents’ best friend for my job — while I was still there,” recalled Edelman, who quickly made his exit, taking with him Libby, who was overseeing children’s shoes.

Now in his mid-30s, Edelman was wooed by the Marciano brothers at Guess and by Ed Finkelstein at Macy’s, and he considered returning to Kenneth Cole Productions.

But while driving Bob Goldman’s fresh-off-the-rack BMW from Germany to the Netherlands, he had an epiphany: “When I got to the hotel in Amsterdam, I called Libby and said, ‘Let’s do it. Let’s start a company called Sam & Libby.’”

What came next is a well-told story: The couple sold his Porsche, a prize-winning horse, their subdivided backyard and everything else but their house to create their own label, which Edelman described as a “young Joan & David.” With authentic marketing starring themselves and their family — plus their now-iconic ballet flat — the brand took off like a rocket, catapulting from $3.2 million in sales in 1987 to over $25 million the very next year.

By 1992, when it filed its IPO, Sam & Libby had revenue of more than $85 million and a year later sold its 7 millionth pair of the Chelsea Bow Ballet. But soon after that, trouble began.

“I think we grew too fast, and we probably were too young to manage the kind of success we had,” said Edelman, adding that he regrets ever taking the brand public. “When you have a bad quarter as a public company, it’s a really big deal. I got a lot of pressure from my board and my underwriters, and I didn’t stick with what I knew I should do. If I’d stayed in our lane, I would’ve pulled out by the third quarter, but there was so much pressure.”

In 1996, the couple sold the brand at a loss to Maxwell Shoe Co., in a move that to this day Edelman describes as the worst thing to happen in his life.

Bruised from that experience, the family attempted another foray with the Naked Feet brand in 1999. When it failed to take off, they left the fashion industry behind and refocused on their ventures in the equestrian world. Sam once again became a full-time horse trader.

Then disaster struck.

Sam & Libby
A Sam & Libby ad campaign featuring the founders.
CREDIT: Courtesy of Edelmans

In 2001, Edelman suffered a terrible horseback riding accident that required seven surgeries over two years that would help him walk again. While some might have been demoralized by the experience, he instead found himself with ample free time to reflect on his past and the state of the shoe business. “It gave me an opportunity to realize how important it was to continue my career, that I didn’t like where I stopped with Sam & Libby, and I wanted to prove to myself that I could do it again,” he said.

Indeed, he has replicated that success with his Sam Edelman lifestyle brand. However, launching his own venture wasn’t the original plan; initially he hoped to go work for Steve Madden. “I really didn’t want to start my own business; I wanted to help Steve explode his. But he didn’t want to do it.”

Eager to get back to work, Edelman also approached PVH and got an audition for the Calvin Klein shoe license. He recruited a young Parsons designer, Megan Key, and nailed the presentation, but when PVH’s lawyers called requesting a $10 million royalty guarantee, the deal fell through.

Once again, the executive turned to his wife: “It was the same conversation from Amsterdam. I said, ‘Let’s start a brand called Sam Edelman,’ and she said, ‘OK.’ ”

They officially launched the business in 2004, and with their team have turned it into one of the top names in the contemporary women’s market, with hit shoe after hit shoe, from the streamlined Gigi thong to this summer’s omnipresent Bay slide sandal.

Since 2017, they have expanded in other lifestyle categories, such as dresses, denim, sleepwear and outerwear.

Edelman credits the brand’s success, in part, to its parent company, Caleres, and to CEO Diane Sullivan. “Diane — and before her, Ron Fromm — they both gave us the runway to truly manifest our talent and our vision, and neither of them ever questioned any part of that plan,” he said. “It was just lights on, gas on, go for it.”

Caleres also gave the Edelmans a gift when it acquired Sam & Libby in 2012 from the now-defunct Jones Group and put it under the couple’s direction. “I didn’t ask Diane to do it; she came to me with it, and she knew it was the right thing to do,” said Sam, now plotting to reinvent the ’80s icon in a way that is “very baby boomer-driven, but with an edge.”

As for his eponymous brand, he has fittingly grand goals: “I’d like Sam Edelman to be a $1 billion brand, and I think we’re well on our way.” Additionally he is continuing to build the Circus by Sam Edelman junior’s line and aspires to make an entrée to the men’s market. “Most of all, I want to see the brands have longevity,” he reflected. As the interview wraps up, it’s clear that Edelman still loves being at the center of it all. “The thing that makes me most excited every day of my life is to get up and work with young people in the fashion business. I don’t think I’ll ever retire.”

Two Ten Gala
Jesse, Sam and Libby Edelman chaired the 2018 Two Ten Footwear Foundation Gala.
CREDIT: Courtesy Image

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