Sam & Libby Edelman on How to Succeed in Business & Their Biggest Mistake

On a Monday afternoon in July, Sam and Libby Edelman are sitting at a dining table in the lobby of their New York showroom with more than a dozen company interns. As the group converses over a home-style lunch — surrounded by furniture and decor plucked straight from the couple’s residence — the Edelmans seem more like doting parents than bosses to the college juniors and seniors gathered for an impromptu meeting.

“Our personal life is our business life, and our business life is our personal life,” Libby said as she and her husband reflected on the decades they’ve spent in the shoe business. “We’ve worked together for a long time, so it’s 
become something that’s just natural for 
us. We complement each other.”

Sam chimed in to complete his wife’s thought: “I think a couple sharing an interest helps with the relationship. Libby and I love fashion. That gives us an extra bond in our 
relationship.” (Sam, who co-founded Kenneth Cole Productions and launched Esprit’s shoe division in 1983, started his career at companies such as Ralph Lauren and Candies.)

Indeed, both their professional and personal pursuits — driven by an unwavering proclivity for shoes — have stood the test of time. Together, they’ve built two companies — Sam & Libby, founded in 1987 — and the thriving Caleres-owned Sam Edelman business, launched in 2004.

Sam & Libby, Sam Edelman
Libby and Sam Edelman
CREDIT: Annie Tritt

“Sam Edelman sales are up more than 115 percent over the last five years due to the team’s talent and the consistent investments we’ve made in the brand,” said Diane Sullivan, chairman, president and CEO of Caleres, which acquired the label in 2010. “It was an easy decision to invest in Sam Edelman — the brand and the person. [He] has been a visionary and legend in the footwear industry for many years, so when he and Libby launched the Sam Edelman brand, we had great confidence that they would create something special, and we wanted to be a part of it.”

Another testament to Caleres’ faith in the pair was its decision in 2012 to buy 
the Sam & Libby brand and 
reunite it with its founders, who sold the business in 1996 — a move Sam calls “the biggest mistake we ever made.”

“They say you shouldn’t switch horses midstream for a lot of reasons — and we should’ve stayed with that horse,” Sam said of his first big shoe project with his wife.

After its launch, Sam & Libby enjoyed blockbuster success: Its bowed ballet flats gained a cult following, selling 7 million pairs in six years. But in 1991, the momentum started to decelerate. After they took the brand public, sales continued to go south, and eventually, they sold Sam & Libby 
to Maxwell Shoe Co. An injury Sam suffered while horseback riding in 2001 would further delay a return to the world of shoes. But as with any true love, the twosome couldn’t stay away for long.

Sam & Libby, Sam Edelman
Libby Edelman at the Sam Edelman HQ.
CREDIT: Annie Tritt

“We don’t spend our weekends watching baseball or football games,” Libby said. “It’s something we just have inside ourselves — this passion for fashion. The most exciting thing [for us] is opening a magazine and seeing a point of view — whether it’s advertising or editorial — or visiting a fabulous city.”

The Sam Edelman brand — which in 
2017 blossomed into a lifestyle collection that includes athleisure, sleepwear, outerwear, 
dresses and denim — has enjoyed an incredible run. But the road has not been without challenges. Perhaps the most daunting of them all is the current climate — defined by erratic consumer spending patterns, fast-fashion 
dominance and the endless aisle of Amazon.

“I sleep worse today than I did in the last 30 years,” Sam said. “[We have] a very important contemporary brand with a tremendous following in a time of complete and total [upheaval] in the world — whether it’s political, economic [or if it has to do with] consumer spending habits. [It’s challenging] staying on top of what’s happening and how we can stay relevant and keep it going.”

Sam & Libby, Sam Edelman
Sam Edelman at the Sam Edelman HQ.
CREDIT: Annie Tritt

Nevertheless, years of positive reception 
at stores like Nordstrom and Dillard’s — 
undoubtedly driven by its founders’ persistent capability of reinvention — should pacify racing nighttime thoughts.

“It’s exciting that customers continue to respond well to Sam’s product . . . After all these years, [he’s] still a student of the business, is always in our stores and freely calls with feedback,” said Kristin Frossmo, EVP and GMM of Nordstrom’s shoe division. “He has adapted as the business has evolved over the years. We would consider Sam Edelman one of our more digitally savvy brands. He never rests on his laurels and is a classic merchant who has figured out how to thrive in a new retail world.”

But it’s not just retail partners who admire the business Sam and Libby have built. Longtime competitor Steve Madden said the label’s success has become a goal post of sorts for his own footwear empire.

“I have so much respect for Sam — he’s just this force of nature I have to deal with,” Madden said. “We’re friends, yet we’re rivals, but more importantly, we respect the hell out of each other. I feel his pain, and he feels my pain because we’re both shoe warriors, and there are not many of us left. I know if our shoes do better than Sam’s, we’re beating the best.”

Skechers founder and CEO Robert Greenberg has also found inspiration from his longtime shoe industry peer.

“I have watched and admired [Sam] for as long as I can remember being in the shoe business,” Greenberg said. “The guy is a cut above the norm with a knack for fashion that not many can equal — and classy to the max.”

As the Edelmans plot the path forward, Caleres is setting robust objectives for the brand, which is seeing momentum internationally. The company enjoys a profitable partnership with Lane Crawford that puts its shoes in stores in Hong Kong, Shanghai, Chengdu and Beijing, China. It’s also landed product placement in the Middle East with Bloomingdale’s Dubai [United Arab Emirates] and Kuwait. In Europe, the label is on the shoe floor at Harrods and Selfridges, and in Central America, it’s available at the El Palacio de Hierro department stores. “We expect international sales for Sam Edelman to triple in the next five years as the brand develops new partnerships in more key cities around the world,” Sullivan noted.

On the home front, the couple’s oldest son, 
Jesse, is steering the brand’s junior’s offshoot, Circus by Sam Edelman — a line that Sullivan believes has “tremendous runway.” The decision to bring their son onboard is consistent with what Sam and Libby wholeheartedly consider their life’s charge: Molding the next generation of shoe industry talent. (The Edelmans are chairing this year’s Two Ten gala and plan to rally the industry around celebrating future leaders.)

“[Jesse] would say he’s been in the [footwear] business for 35 years — that’s how old he is,” Libby said. “He’s one 
of our young people, so he’s also learning. He’s part of our senior management team, so he’s got a big responsibility, and he’s taking charge.”

Similarly, Sam effortlessly recounted his son’s accomplishments: “He’s very independent and runs his own business, [which is] highly profitable,” he said. “Jesse is a tremendous help to us. I don’t think it’s something I’d trade for the world. He balances me and Libby beautifully. He’s a born-and-bred shoe man.”

While they’ve found immense value in surrounding themselves with a team of young people — evidenced by the group of college students who have joined them for lunch on this rainy afternoon — Sam and Libby understand that the millennial generation is decidedly different from their own.

“It’s very hard for people our age to understand why you wouldn’t want to buy or drive a car, or buy a house ­— and why you wouldn’t want to work 15 hours a day or give up all your weekends,” Sam said, directing his response to the students gathered in his showroom. “It challenges us to learn about a new generation and the way you communicate with each other. If someone tells me they just talked to somebody an hour ago — that means they texted them and the text was three words. But that’s normal now.”

As if on cue, a student tossed out an unexpected question: “Would you guys ever do a men’s line?” he asked.

“We haven’t thought about doing men’s for a while — it’s not natural for us to think about,” Sam responded contemplatively. “But if I could find a way to do something for men that would make them happy, it would be innovative, whimsical and have quality and integrity and some kind of moral intelligence to it. But that’s the good thing about working with young people — you bring up ideas like that.”

Libby interrupted her husband with the intern’s newest assignment: “That could be your project for 
the rest of the summer,” 
she quipped.

More From Our Brands

Access exclusive content