The Harry Rosen Story

From dropping out of High School earning $211 million in annual revenue in 2023, Harry Rosen has forever transformed men’s fashion.

Upon his passing on Christmas Eve 2023, at age 92, there was a worldwide echo resounded his kindness and artistry.

We deeply admire the grace Harry Rosen carried himself with. 

He had a non-judgmental style of creating excellence and elegance from how he structured his business, to his client relationships and product quality. 

We strive to inspire others to carry themselves with the same level of competence and confidence through financial literacy that Harry Rosen did through clothesmanship.

Let’s unravel how Harry Rosen stitched a legacy from one small store to twenty Canada-wide.

In his youth, Harry Rosen worked at his father’s scrap metal business and a small menswear haberdashery in Toronto.

In his twenties, a family member gave him a life-changing $500 loan. This allowed him and his brother, Lou, to open a menswear store on Parliament Street in 1954.

Harry’s level of service was beyond selling suits. His meticulous attention to detail and listening skills were distinguishable. 

He asked customers thoughtful questions about their lives outside of their professions, helping them find clothes that fit their personalities just as much as their physiques.

During a trip to New York, he was inspired by the natural-shouldered suits he saw men wearing. He made the style available in his store, calling it the “Cambridge Look” and it soon became in high demand.

Ask Harry Campaign

In the 60s, an advertising executive named Stan Burkhoff began shopping at Harry Rosen. 

Stan offered to create advertising campaigns for Harry in exchange for two suits, one for himself and for his art director, Reid Bell.

Wisely, Harry agreed, leading to the timeless ‘Ask Harry’ Campaign, which has been active for over 67 years.

The campaign includes Q&A-style print ads with questions like:  

How much of a shirt sleeve should show at the wrist of a sports jacket?

This campaign helped canonize Harry as a men’s style expert. 

Business Values

Harry Rosen was well-known for his warmth and authenticity.  

In 2014, Harry Rosen invested more in employee training than any other Canadian retailer.

Harry Rosen team members are educated on client relationship management (CRM) tools and menswear craftsmanship. 

He would not allow men to purchase unflattering outfits. In Harry’s words: “Treating customers as individuals is the real business we’re in”.

Dylex Limited

In the late ’60s, Harry Rosen sold his business to retail giant, Dylex Limited, where he became CEO of its menswear division. 

Access to Dylex’s Warehousing & Logistics allowed more Harry Rosen locations to open across Canada.

Harry bought 51% of his business back in 1975. After tumultuous back-and-forth lawsuits, Harry secured the other 49% in 1995.

Conclusion

In the 70-year lifespan of Harry Rosen, exceptional customer care has remained a constant. 

In 2004, Harry became an Order of Canada recipient. He was honoured for his philanthropic involvement in the Canadian Paraplegic Association and the Cancer Care Fund.

His grandson Ian stated:

“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.

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.”

Next time you pass a Harry Rosen store, you can be inspired by the conviction that a young man put into what is now a menswear institute — all while remaining humble and kind.

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Have you ever shopped at Harry Rosen? What was your experience? Let us know in the comments!