Tip Top Tailors Building in 1930 & 2026

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Looking east on Fleet St from Gzowski Blvd, towards Lakeshore Blvd W in the Fort York and Bathurst Quay neighbourhoods of Toronto.

The archive photo shows TTC track work being done on the Fleet St extension nearly a century ago. The background features the Tip Top Tailors building and a part of the former Maple Leaf Stadium on the left.

The Tip Top Tailors building was completed in 1929. David Dunkelman, the founder of the menswear company, commissioned architect Roy H. Bishop to design this Art Deco-style building, which served as the company’s headquarters, factory, and warehouse. In the early 2000s, this heritage-designated building was transformed into Tip Top Lofts, with an additional five-storey structure made of industrial frame and glass added on top.

Maple Leaf Stadium stood from 1926 to 1968 and was home to the professional minor league Maple Leafs baseball team.

Then and Now

July 22, 1930/October 17, 2026 – Looking east on Fleet St from Gzowski Blvd, towards Lakeshore Blvd W in the Fort York and Bathurst Quay neighbourhoods of Toronto.

The archive photo shows TTC track work being done on the Fleet St extension nearly a century ago. The background features the Tip Top Tailors building and a part of the former Maple Leaf Stadium on the left.

The Tip Top Tailors building was completed in 1929. David Dunkelman, the founder of the menswear company, commissioned architect Roy H. Bishop to design this Art Deco-style building, which served as the company's headquarters, factory, and warehouse. In the early 2000s, this heritage-designated building was transformed into Tip Top Lofts, with an additional five-storey structure made of industrial frame and glass added on top.

Maple Leaf Stadium stood from 1926 to 1968 and was home to the professional minor league Maple Leafs baseball team
July 22, 1930/October 17, 2026 – Looking east on Fleet St from Gzowski Blvd, towards Lakeshore Blvd W (City of Toronto Archives, Globe and Mail fonds, Fonds 1266, Item 21234)
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