From the ‘60s-zeitgeist clogs of Woodstock to the hiking and climbing boots of the Shawangunks and snow boots for our robust winters, shoes are a chief component of Mid-Hudson Valley life. Keeping up with everyday footwear as well as style trends and recreational models is Pegasus Footwear, a member of the community for 25 years.
The brainchild behind the Pegasus empire is laid-back Len Sapiro. It was a circuitous route he took to be the wizard of Woodstock footwear, from a Masters degree in sociology to a stint in his father’s auto parts store to managing a head shop in the early ‘70s in New Brunswick, NJ. He dubbed his first solo business Pegasus.
When a restaurant fire next door burned the shop to the ground in 1978, Sapiro reinvented himself, opening a new store nearby for blue jeans and tops. This venture was also named Pegasus. It was a success. In the early ‘80s he opened a second store across the street dubbed Pegasus Too and offered Frye boots and wooden clogs.
“This was my first foray into footwear.” Little did Sapiro know how prominently footwear would figure in his business career.
After working at the Omega Institute for a few summers, Sapiro fell in love with the Valley and relocated to Woodstock in 1988. That summer, he opened Pegasus Footwear in a tiny 400-square-foot store on the edge of Woodstock.
The new enterprise was not an immediate success.
“The first few years were a struggle,” Sapiro recalled, “as I was running the store by myself, with some part-time help. I was working six days a week. The store was so small, I had to keep some inventory in my garage, and when I began to date the woman who lived in the upstairs apartment next to the store, I kept inventory up there too.”
The woman who offered storage space would eventually offer her heart; the pair has been married for 23 years.
Better times were soon to come. Pegasus moved to its present location in 1998. In 2002, a second location opened its doors in New Paltz with a greater square footage than the Woodstock store. In the summer of 2012, Sapiro opened Pegasus KIDS Shoes, right next to the New Paltz store.
Pegasus Shoes currently offers more than 75 brands, serviced by a staff of 14—seven full-time and seven part-time.
“All of my staff is really ‘into’ shoes, and it shows,” Sapiro said. “Most of my full-time staff has been with me for several years. It takes a good bit of time and energy to train our sales associates to enhance the customers’ buying experience.”
In 1999, Pegasus launched a website for online sales to sell their shoes beyond the Valley. Sales grew steadily every year, attracting customers across the globe. However, profits began flagging in 2007, as chain store conglomerates gobbled up the majority of online sales. Sapiro was forced to downsize his Internet sales operation and now only offers clogs online.
However, there is still room for growth: This March, Pegasus Footwear will open the doors to a third store in Rhinebeck.
Len Sapiro admits, jokingly, that a shoe fetish guides his business philosophy.
“Shoes are my passion. I don’t exactly know why—maybe it has to do with colors, textures, shapes, and mechanics. I still get excited when I see the next season’s collections. I have traveled all over the world searching for the most innovative footwear. For me, the buying process is the most fun.
“I love shoes, and tend to buy more shoes than I should,” he admits. “This is great for our customers, but sometimes not so for the bottom line.
My goal for Pegasus Footwear has always been to simply have the best shoe store I can.”
Pegasus Footwear
10 Mill Hill Road, Woodstock: 845-679-2373
27 N Chestnut St, New Paltz: 845-256-0788
3 East Market St, Rhinebeck: 845-876-7474
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