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Remembering Harry Rosen

August 27, 1931 - December 24, 2023

It's with profound sadness that we share our founder and visionary, Harry Rosen, passed away on December 24th, 2023 at the age of 92, surrounded by his loving family.

For those that had the privilege of working with Harry, this news will be felt with sorrow. His passion for menswear and fashion was contagious; his ability to teach and inspire was unparalleled. For those that never had the opportunity to meet Harry, just know that so much of what our company looks like today stems from his incredible drive to outpace client expectations.


Born and raised in Toronto, Harry joined a small menswear haberdashery on Bloor Street that would ignite his passion for menswear and customer service.  In 1954, he accepted a $500 loan from a family member and opened his own menswear store alongside his brother Lou on Parliament Street in Toronto’s Cabbagetown.

With limited inventory, they filled the shelves with empty boxes and bolts of fabric on loan from a supplier and began creating made-to-measure clothing for men.  Harry set himself apart  with an unmatched focus on keeping customer information organized with detailed notes on preferences and everything in their life that might be relevant to building trust and providing unparalleled customer service.

In 1957, Harry took a trip to New York City and loved the natural shouldered suits worn by the advertising men on Madison Avenue. He bought a sample and took it back to his partners at Coppley Apparel, a Canadian clothing manufacturer, to duplicate. Harry called this the “Cambridge Look” which would be sought out by younger executives in Toronto. The business began to take off.

In 1961, Harry would take another huge risk, moving his shop to a location over 10 times the size on Richmond Street (intersecting with Bay) to serve the denizens of Bay Street. This risk paid off, as the name Harry Rosen started to become synonymous with menswear in Toronto.

A few years later, Harry began working with an advertising agency and started the ‘Ask Harry’ campaign, which would reinforce Harry as the expert in menswear. This campaign and personality remain core to the Harry Rosen brand today. Harry Rosen is trusted with empowering men to discover their individual style using our personalized service. ‘Ask Harry’ would answer questions that men needed answers to, including “how long should my trousers be?”  or “how much sleeve should I show over the cuff of a suit?”.


In 1968, Harry entered into an agreement with Wilf Posluns at Dylex Limited to acquire the Harry Rosen business.  Harry was appointed CEO of their newly established menswear division, which included Tip Top Tailors, their manufacturing business and Harry Rosen stores.  During his tenure at Dylex, Harry opened additional Harry Rosen stores and would convert Tip Top Tailors from a made-to-measure retailer to the largest ready-to-wear menswear retailer in Canada.

Despite his success, Harry was keen to return to his entrepreneurial roots. In 1975, Harry purchased 50% of Harry Rosen back from Dylex, and partnered with their capital and expertise in real estate, logistics, and warehousing to expand Harry Rosen across the country from Vancouver to Quebec City. In 1995, Harry and the Rosen family purchased the balance of the company back from Dylex and was once again family-owned.


Harry’s visionary approach helped cement Harry Rosen among the world’s top retailers. Harry was the first to source luxury Italian designers such as Ermenegildo Zegna and Giorgio Armani in the Canadian market. He helped develop fashion labels such as Hugo Boss and Polo Ralph Lauren. His focus on delivering for each individual customer never let up, and this passion inspired teams across the country for decades.

The foundations Harry built have endured.  He personally trained his eldest son Larry, who joined the business in 1986, on all aspects of the business with an eye to succession.  The company now has a third generation of Rosens aboard with Grandsons Ian & Graham in executive roles.


Rosen’s legacy will endure through the mark he has left on Canadian luxury menswear, and his role in establishing the trusted brand to help men discover their individual style. “While the world of fashion and how we shop for clothes has changed, the core principles of my grandfather’s vision remain unchanged for us,” says Ian Rosen, President & Chief Operating Officer of Harry Rosen Inc. “Men want a curated and relevant point of view, men want uncompromised service, men want trusted and personalized recommendations. We continue to build on his vision leading into the celebration of Harry Rosen’s 70th anniversary in 2024.”

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