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Harry Rosen, a legendary merchant who redefined the upscale Canadian menswear market, died on Christmas Eve at the age of 92.

Rosen, who passed away in his hometown of Toronto surrounded by his family, was one of the industry’s most highly respected retailers. The company that bears his name operates 19 stores across Canada and has sales of some 350 million Canadian dollars. The business is currently run by his son Larry, while his grandson Ian, Larry’s son, oversees digital efforts for the company.

“It’s with a heavy heart we announce the passing of our founder and visionary Harry Rosen,” the company wrote on its LinkedIn page on Christmas. “Starting with a $500 loan and a dream, Harry willed our business into existence one client at a time. His passion for menswear and fashion was contagious; his ability to teach and inspire was unparalleled. The team he built and the values he instilled have helped our business span across the country, three generations, and nearly 70 years. Words simply can’t summarize the impact he had on all of us. Rest in Style.” 

“It’s hard to summarize the legacy Harry leaves behind in words,” Ian Rosen wrote on LinkedIn. “For anyone that had the privilege of seeing him in action, you quickly saw his success was no accident. He was an expert not only when it came to clothing, but people too. Simply put: everyone felt better when Harry was around.”

He continued: “The Harry Rosen story is the ultimate entrepreneurial endeavor. With a $500 loan from a family friend, he and his brother Lou opened a 500-square-foot shop with no inventory. With boxes and bolts of fabric making the shelves feel full, they built the business client by client. His keen eye for fashion helped him establish the ‘Cambridge Look’, a natural-shouldered garment that quickly became the look of choice for young executives in Toronto.

“A series of bold moves would help Harry take the business to new heights. First, moving his store to Richmond Street into a location 10 times the size, so to be closer to the denizens of Bay Street. Second, developing a partnership with Dylex Limited (and Wilf Posluns) to leverage their capital and expertise in real estate, manufacturing and supply chain to take Harry Rosen across the country. Third, being a pioneer with new brands; Harry was the first to sell luxury Italian labels such as Giorgio Armani and Ermenegildo Zegna in Canada and built incredible businesses with the likes of Hugo Boss and Polo Ralph Lauren.”

Bob Mitchell, co-chief executive officer of Mitchells Family of Stores, said: “Harry was one of my mentors. I traveled with him for decades through Italy and his passion for product combined with being a hands-on merchant was really inspiring to me. I’ll miss him dearly.”

Although Harry stepped back from the day-to-day operation of the business in 2005, he still served as an ambassador, often stopping by one of the stores to chat with customers. Larry Rosen has been CEO since 2000. 

In a 2018 interview with WWD, Larry Rosen said of Harry: “My father is a real entrepreneur. He’s a guy who wills business into existence — he’s brilliant. He and his brother Lou started in 1954 and in 500 square feet, they built a made-to-measure business. They really started by bringing a look to Canada that Canada didn’t have. In those days it was called the Brooks Brothers look: the Madison Avenue, natural-shoulder look. He actually went down to New York, bought a suit, took it to a local maker named Coppley and they duplicated it. And all the young executives in Toronto flocked over there. He was so successful that by 1961, he moved the business to a great location in the heart of Bay Street, which is our Wall Street. He built a very large business and then expanded to a second store in Yorkdale in 1968; Bloor Street was the third in 1970. Then in the early Eighties, he started expanding across the country.”

In addition to his retail expertise, Harry Rosen was a philanthropist. Over the years, he was involved with the Canadian Paraplegic Association, Corporate Fund for Breast Cancer, Cancer Care Fund, Mt. Sinai Friends for Life campaign, United Way, Center for Addiction and Mental Health and the University Health Network. He was on the board of governors of Toronto Metropolitan and Western Universities and Mt. Sinai Hospital and was the recipient of the Order of Canada, a recognition of outstanding merit or distinguished service by Canadians, in 2004. 

In addition to Larry and Ian Rosen, Harry is survived by Evelyn, his wife of 68 years; his other children, Andrea, Wayne and Racheal; eight other grandchildren, and six great-grandchildren.

Services will be held Thursday at Temple Sinai in Toronto. The family requests that any donations made in Harry’s memory go to the CAMH or The Baycrest Foundation.