Diane Shoes, one of Windsor's longest-running businesses and Canada's oldest family-run shoe store, may be nearing closure after 135 years in operation. The owners have put the store's building at 1329 Ottawa Street up for sale and plan to eventually move out, with the current location possibly open for another year and a half depending on market interest.
Owner Cites Changing Times
“The world is changing a little bit, and we might have to change along with the times,” current owner Carl Weingarden told the Windsor Star on Wednesday. “Maybe Ottawa Street isn’t the street to be on for retail anymore and maybe we should be looking elsewhere.” Weingarden, 66, said he is not in a hurry to sell but noted the store could close sooner if the building sells quickly. He added he might move to a smaller location to stay in business for a little while longer. “I’m sixty-six, but a young sixty-six, so I’d rather not retire so early,” he said.
Four Generations of Family History
Established in 1891 by Isaac Weingarden, the business spans four generations of the Weingarden family. Carl, Isaac’s great-grandson, started working at the store at age 11. Carl’s father Jerry Weingarden, 90, still comes in to work a few hours every morning. “He’s due to retire,” Carl said. Carl’s own children are not interested in continuing the business, so the store will close once he retires. At its peak in the mid-20th century, the family owned four shoe stores in Windsor—three for women and one for men—consolidated into Diane Shoes in the 1950s by Carl’s grandfather Max Weingarden.
Economic Challenges and Online Shopping
The store has weathered numerous economic cycles, but current conditions “may be one of the toughest,” Carl Weingarden said. The rise of online shopping, accelerated by the COVID-19 pandemic, combined with an economic environment where customers spend less, has slowed business considerably. “We’re definitely in a recession whether the government wants to admit it or not,” he said. The neighbourhood has also evolved: “At one time, Ottawa Street was 99 per cent retail. Now it’s maybe like two per cent. So, we’re more of a destination shop than we were before. The plazas and malls have stolen a lot of that, and a lot of the independent stores have closed up.”
A Labour of Love
Weingarden said Diane Shoes has “always been a labour of love” that he hopes to continue in one form or another. “I wouldn’t mind working either full time for a while or part-time (in another location). Whatever happens, I want to keep busy. I want to do something.”



