If you want a Maple Leafs jersey that hits most of the highlights of Toronto's hockey history, look no further than this entry by David Kerr. He writes: 

The logo builds off two of Toronto’s oldest pieces of hockey history. 

First, the University of Toronto Varsity Blues Hockey Club (est. 1891) who represented Canada at the 1928 Olympics, winning the gold medal. The Varsity Blues also have the longest running hockey program in the city of Toronto.

Second, the Toronto Arenas (est. 1917), the precursor to the Maple Leafs. The Arenas were a member of the original NHL. 

The sweater design is reminiscent of the 1934-1937 uniform worn by the Toronto Maple Leafs during some of the first years that the franchise spent in the historic Maple Leaf Gardens.