David Dunkelman Sr. Clothing founder, Tip Top Tailors

A Stitch in Canadian History: David Dunkelman & Tip Top Tailors

On my walk through Dawes Road Cemetery in Toronto’s east end, I discovered the final resting place of a Canadian retail giant — David Dunkelman Sr., founder of the iconic Tip Top Tailors.

In 1909, Dunkelman opened his first store at 245 Yonge Street, just five doors south of the historic Pantages Theatre. The brand name, Tip Top Tailors, came from a customer contest — a clever marketing move that helped cement the company in the public’s mind. At the time, a “good” suit cost around $14.

Business grew rapidly, not only catering to everyday consumers but also manufacturing uniforms for police forces and the Canadian military. As demand soared, Dunkelman commissioned the construction of what became one of Toronto’s most iconic Art Deco buildings at 637 Lake Shore Boulevard West — a factory and warehouse just minutes from the CNE Princes’ Gates, and adjacent to the old Toronto Maple Leaf Baseball Stadium (sadly demolished in 1968). Today, that landmark building lives on as Tip Top Lofts, a blend of historic preservation and modern living.

In 1948, upon David’s retirement, leadership passed to his son Benjamin Dunkelman — a decorated Canadian Army officer (Queen’s Own Rifles) and Israeli war hero who fought in the 1948 Arab-Israeli War. Under Ben’s leadership, Tip Top Tailors expanded to a 52-store empire.

Eventually, in 1967, the Dunkelman family sold the company to Dylex, a retail powerhouse whose portfolio would come to include brands like Fairweather, Suzy Shier, Thrifty’s, Town & Country, Harry Rosen, and Big Steel Man.

David Dunkelman Sr. passed away in 1978 at the age of 95, and Ben in 1997 at 84. Both are buried together in the family plot at Dawes Road Cemetery — a quiet resting place for a family that helped shape the Canadian retail and fashion landscape.

1889-1949