By Kenneth Pastushyn

For generations, Diane Shoes has been a Windsor institution, proudly family-owned since its founding 135 years ago. Now, after four generations, this storied chapter is coming to a close.

“We’re the oldest family-owned shoe store in Canada and probably the oldest family-owned small business in Windsor,” says Jerry Weingarden, the 91-year-old third-generation owner, from the shop’s familiar 1329 Ottawa Street location.

The story of Diane Shoes began in 1891, when Jerry’s grandfather Isaac immigrated to Canada from Russia and opened a family clothing store specializing in footwear. Named “The Model Store,” it was located on what is now University Avenue East, just steps from today’s casino.

In the 1920s, Isaac’s sons Max and Dan launched their own women’s shoe stores along Ouellette Avenue. The name “Diane Shoes” was coined by Max in 1928, inspired by seeing Joan Crawford play Diane in the silent film “Our Dancing Daughters.” Max thought the name was elegant, and it fit the trend of giving women’s shoe stores feminine names. Max and Dan also owned Sally, Marilyn, and Baker Shoes.

Their pricing—$1.99, $2.99, and $3.99—was accessible at a time when five dollars was a week’s wage for many. “My uncle and dad made their money during the war years,” Jerry recalls.

As a young man, Jerry joined the business, starting as a stock boy for his father.
In 1950, Sally, Marilyn, and Baker Shoes were consolidated into Diane Shoes. He moved the business to Ottawa Street, which, along with downtown Ouellette Avenue, was one of Windsor’s shopping hubs at the time.

“We’ve always tried to be a step ahead,” Jerry explains. But change was constant: in 1970, the opening of Devonshire Mall and other suburban shopping plazas forced Diane Shoes to adapt again, shifting focus to high-grade shoes and specialized sizes. “We went from popular shoes to high-grade shoes and specialized sizes,” says Jerry, who by then had taken over from Max and Dan.

Throughout the decades, the Weingarden family-built Diane Shoes’ reputation on quality merchandise, a wide range of sizes, and attentive service—offerings that set the store apart from chain shoe retailers. “Most chain stores don’t carry the proper width sizes,” Jerry notes.

What’s the secret to Diane Shoes’ longevity? “Persistence and stubbornness,” Jerry answers with a smile. There were good years and tough ones—like the late 1980s, when a new Ouellette Avenue location was opened but ultimately closed in the mid-1990s due to declining American customers.

The tradition continued with Carl Weingarden, Jerry’s son. Like previous generations, Carl began as a stock boy, then became a salesman and manager. After 9/11, they shifted the store’s focus toward casual footwear. Carl also purchased Al Boulaine Shoes, renamed it Arden Shoes and moved to Ottawa Street. For a decade, Arden and Diane Shoes co-existed before merging. Jerry entered semi-retirement, still stopping by in the mornings and enjoying golf by noon.

Now, as Diane Shoes marks 135 years, the family prepares for its final chapter. Carl, now 66, is looking toward retirement. The decision to close—driven by high inflation, the rise of online shopping, and lingering pandemic challenges—was not easy.

The Ottawa Street store is up for sale, but Diane Shoes will remain open until the building is sold.

As for what will be missed? Jerry reflects, “A lot of people who have difficult sizes, who care to come into this store, are going to have a difficult time finding the widths and sizes we carry. And as long as we are open, special orders will still be available.”

The end of Diane Shoes marks not just the closing of a business, but the fading of a family legacy built on generations of service, resilience, and care.