Canadian fashion retailing legend and philanthropist Harry Rosen has died at 92.

Mr. Rosen’s eldest son, Larry, the chairman and chief executive officer of Harry Rosen Inc., announced the death of his father on Christmas Day. He said his father, who died a day earlier, leaves behind a rich legacy as the “founder and visionary” of the prominent men’s wear company that now spans three generations.

“If there’s a lesson in my father’s life, it is that with passion and an entrepreneurial spirit, you can build a real, legendary business. He was the entrepreneur’s entrepreneur,” Larry said in an interview on Monday. “He was great with people and he always drove forward, and always in an enthusiastic way.”

The Harry Rosen empire has humble roots in Toronto’s Cabbagetown neighbourhood where, in 1954, Harry and his brother Lou opened a small made-to-measure men’s clothing store with “$500 and a dream.” Like any great entrepreneur, Larry said his father willed business into existence by attracting customers, asking for referrals and not being afraid to take risks.

It was there that Harry had a vision to create a global men’s boutique that would “help men feel good and do good” by wearing well-crafted clothing that catered to their personality. And he did just that.

In 1957, he returned home from New York and introduced the natural shoulder suit that was popular across the border to young Toronto executives. It became known as the “Harry Rosen look,” Larry said, and people flocked to his father’s 500-square-foot store to get one of their own.

“He became fantastically successful in this really crazy, out-of-the-way location,” Larry said. So, he took another risk and opened a store 10 times as large on Bay Street – “It was a huge success.”

Soon, people were coming to Harry for fashion and lifestyle advice in ask-me-anything-type advertisements that ran in The Globe and Mail, Larry said. He answered questions, such as: How long should a jacket be? How much cuff should you show? How do you build a suit? He started to become a household name.

By the 1980s, Harry Rosen had expanded across Canada with stores from British Columbia to Quebec. It became – and still is – the largest men’s retailer in Canada.

Harry was among the first to source luxury Italian designers, such as Ermenegildo Zegna and Giorgio Armani, into Canada. He also helped to popularize fashion labels such as Hugo Boss and Polo Ralph Lauren.

But, no matter how much the company grew, Larry said his father never forgot his roots, to deliver for each and every customer.

One of the funniest stories Larry said his dad used to tell was about driving through a snowstorm to deliver a suit to a man in Hamilton. “The guy said, ‘I’ve never seen customer service like this my entire life,’ and was so pleased,” Larry remembers. “In those days, we used to give credit. The guy never paid. [Harry] says: ‘The son of a gun never paid his bill.’ “

Harry was still sizing and fitting customers out of the trunk of his car in the early 2000s and would pause executive meetings to speak with customers, over something as small as a bad pair of socks, Larry said.

“We had to put everything on hold because, for Harry, the customer was always his greatest passion, his first priority,” he said. “Every day, everybody in our stores thinks about, ‘What would Harry do? How would Harry care for this customer?’ That’s really the cornerstone of our success. He really set the bar.”

In 2004, the consummate retailer was named to the Order of Canada for his contributions to the business world.

“Harry Rosen is Canada’s leading retailer of high-quality men’s wear. Renowned for his integrity, marketing skills and business acumen, he shares these abilities equally as a community builder,” said a statement in his honour, which listed his support for a number of organizations, including the Canadian Cancer Society, United Jewish Appeal and Canadian Paraplegic Association.

In 2010, Harry was honoured for raising about $1.8-million for stem-cell research.

Harry stepped back from the day-to-day operations of Harry Rosen Inc. after 51 years in 2005 and his son, Larry, took over as CEO with guidance from his father.

“Sometimes it was tormentor,” Larry said, laughing, “but most of the time, he was mentor and he was an extraordinary teacher.” His father is still at the heart of everything the company does.

Harry, who was diagnosed with Alzheimer’s about three years ago, leaves his long-time partner Evelyn, his four children, nine grandchildren, six great-grandchildren “and countless family and friends whom he was always there for,” Larry said.

“We’re grateful for the long life he had but we’re even more grateful for the legacy he’s left for all of us.”