The “I Hate Rubber Boots” guy is becoming a fixture around downtown Toronto. The first time I saw him was in June 2018 when I was carrying my Konica T3 loaded with 35mm black and white film. This time, I was carrying my Sony A7R IV. I saw him in the distance walking north up Yonge Street. Anticipating his approach, I dropped to my knees. Instead of approaching, he stopped and posed, but I was shooting with a 35mm lens and he was still just a small figure in my frame. I motioned him to keep walking and he obliged. Better an action shot than posed, not that walking is much of an action.
In The Global Soul, Pico Iyer includes an extended meditation on Toronto. He observes that the people of Toronto have a well developed sense of irony. The “I Hate Rubber Boots” strikes me as typical of that sensibility. We all hate rubber boots but go on wearing them anyways. Same goes for masks.