The examples given at the start of this thread deal with the architecture of individual buildings. In that department, we are probably okay, but I've found that what gives a city a good, urban feel is consistency of some sort *across* different buildings, in size, massing, style, etc.
One thing that makes Toronto feel "messier" than a lot of great world cities, regardless of the architecture of individual buildings, is the total inconsistency of size and style. We have 30 storey glass condos next to 2 storey 19th century shops, next to 10 storey office buildings from the 50s. I personally have grown to enjoy this aspect of the city, but it does preclude the sort of grand feel that you get from Parisian boulevards and Manhattan canyons, due to their consistency. Even in Tokyo, where most individual buildings are forgettable, some areas achieve that grand feeling solely due to consistency of scale.
If Toronto started to move away from its fairly laissez-faire approach to scale to the extreme of designating certain boulevards to be exactly, say, 7 storeys, no more and no less, it might achieve that grand feel in places. Would that be make sense, or be worth it, I'm not sure.