You might be familiar with this photo already, since it apparently inspired a mural on the side of the Rhino in Parkdale. It was taken at the very first Miss Toronto pageant ever, which was held in 1926, back when people made their bathing suits out of wool. The event was held at the Sunnyside Bathing Pavillion (which is still there) down by the lake. The organization of the event was eventually taken over by the Toronto Police about a decade later and moved to the CNE grounds.
They picked a Miss Toronto every year until 1991, when, it seems, we finally woke up to the whole tasteless objectification of women thing and decided maybe it was time to stop doing it. UrbanToronto has more photos of the pageants from over the years here. It's well worth a click-through and a scroll-down to get a quick and vague impression of how our city's idea of a superficial feminine ideal changed over the course of the century.