Based on personal experience, Toronto weather is unpredictable at best. It can be brutally cold and wet, beautiful and warm, or windy as hell all in the same day. Canadians have to keep practicality in mind, so layering is popular. Furry and cozy is comfortable AND a way to incorporate a dramatic coat.
Canadians have always prided themselves on diversity, (in school, we called ourselves the "mixed salad" in contrast to the Americans' "melting pot"). You see this reflected in the way that people style cultural silhouettes and patterns into modern chic ensembles. Ethnic prints are cut into great silhouettes. Traditional hairstyles are accessorized with statement pieces.
Let's not forget the Canadian sense of humor. The fashionistas in Toronto look gorgeous, but they don't take themselves too seriously. One thing I observed in the images of people posing in front of fashion shows in other cities and in Toronto is that you find people here laughing and smiling (unless they are doing a deliberate impression of a bad "blue steel").
What defines street style in your city?
Photos by Katherine Wong