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

SOURCE
- City of Toronto Heritage Register
- Heritage Toronto
- Heritage Toronto: Tip Top Tailors plaque
- Heritage Toronto: Maple Leaf Stadium plaque
- Ontario Heritage Trust
- Photo: Denise Marie for TorontoJourney416
- Vintage Photo: City of Toronto Archives
- City of Toronto: Maps
- Toronto City Directory courtesy of Toronto Public Library
