Pegasus Footware marks 30th year

Len Sapiro (photo by Dion Ogust)

In an age where one can buy anything with the click of a mouse or the tap of a touchscreen and have it arrive in a day or two seemingly by magic, many brick-and-mortar retail stores find it impossible to compete. That’s where Pegasus Footwear is different. This week, the store is celebrating the 30th anniversary of its humble beginnings in Woodstock.

Owner Len Sapiro got his retail start at a head shop in New Brunswick, N.J., named Pegasus. He sold the usual stuff, pipes, papers, paraphernalia and psychedelic posters in the early 1970s. Fast-forward to 1988, when he moved to Woodstock and opened a small shoe store near the current 10 Mill Hill Road location and the rest is history.

“I started with a shoe store down the street, which has worked into this store for the past 18 years or so,” Sapiro said. Since then, the store has grown each year and there are now three locations. He opened in New Paltz 16 years ago and Rhinebeck six years ago.


“I love shoes. I don’t know why. I think it’s the colors and the texture and the feel of them and the fact that I’m actually doing something good for people by putting them into good shoes,” he said from his back office in Woodstock, occasionally sneaking a glance into the retail space.

Between the three stores, he employees about 18 people both full-time and part-time.

“It’s hard to believe it’s 30 years,” he said.

A competitive edge in the Internet age

Sapiro said he can think of three main reasons why he can still keep the doors open and the lights on in his stores.

“One is we really work hard and enjoy picking what shoes we sell here. The buying is the most important thing,” he said. “My staff helps me do some of the buying, but we really search out, not just the major brands that we carry but we search out really interesting smaller brands.”

Sapiro said having a good employees is key. “I’m blessed with a really good staff in all three of my stores. They all love shoes and they’re really into helping people get the right shoes as opposed to just selling them anything, which is really appreciated.”

And the third reason is what Sapiro calls his “wonderful, loyal base of customers” who prefer a small-store experience to surfing the web. Pegasus does not do any online sales, though it spreads the word on social media, including Facebook and Instagram and has a robust email list built over the years.

“I focus on my three stores. I try and put all my energy into making all three of them the best shoe stores I can,” Sapiro said. “We have three good stores. All of them are profitable to one degree or another.”

Sapiro tries to make sure inventory is stocked in each of his stores to keep efficiency high and costs down. Inventory is cross-checked regularly on the computer and each Tuesday, shoes are swapped via van between the three stores.

He also tries to keep his prices a buck or two lower than

Employee test-driven and approved

The technology of footwear has changed dramatically over Sapiro’s 30 years in the business and continues to evolve, so the store is constantly testing new product lines.

“Every one of the shoes we have in here is test driven by one of our staff,” Sapiro said. “Somebody tries it on, walks around in it, whether we’re at a shoe show or we’re here,” he said. “They tell me these feel really great or they’re too hard here or they don’t fit here. We base the majority of our buying experience on that. We want people to try on shoes and say I love these shoes, not just sell them any shoes.”

That’s the difference from buying online or even at the big chain stores.

“We see people walk in here all the time with the wrong fitting shoes. I can’t say anything to them but they obviously bought them at [another store] or something, tried them on themselves, saw they looked good and walked out, but they’re not that good,” he said.

“My staff is really into making sure people get the right fit. Do we do it 100 percent? Probably not, but we get pretty close to making sure people walk out of here with the right fit.”

Sapiro said keeping good relationships with brands and vendors helps him keep a quality selection that keeps customers coming through the doors. 

“I have a very, very good rapport with all the companies we deal with. They respect me. They respect our stores, and we have a very good working relationship, which gives me the advantage of procuring what’s the best stuff,” he said.

The three stores stock a combined 20,000 pair of shoes ranging from sandals to clogs to shoes to boots. Styles change with the season, so Sapiro has a shoe school for his employees.

“We have [one] in the fall and in the spring again because the product mix changes,” he said. “Hopefully my staff has as much information about shoes as they can.”

Besides style, employees need to learn about fit. As we’ve all experienced, shoe sizes can very by brand.

“Even within brands, different collections fit differently,” he said.

“Birkenstocks were huge when I started here in ‘88,” Sapiro said. “Then they died off for about 10 years and now the last three or four years, they’ve come back to be even stronger than they were the first time,” he said. “Birkenstock is now being sold to mothers, grandmothers and the kids.”

UGG boots and sandals were all the rage about 10 years ago and now they’ve been in a steady decline. “I think they made the mistake of selling to everybody,” Sapiro said. “We still sell them, but not the numbers we used to. We used to get a warehouse full of them. We don’t do that anymore.”

Sale to mark 30th anniversary

On August 10-12, all stores are having a 30 percent off sale on summer shoes and sandals. “Except Birkenstock, which simply won’t allow us to discount their shoes. They’re too good,” Sapiro said.

Pegasus locations are 10 Mill Hill Road, Woodstock; 3 East Market St., Rhinebeck and 27 North Chestnut St., New Paltz.