I hear you, Toronto/Ottawa/ Montreal streets are murder on footwear. Kingston was really bad, too. The freeze/ ice/ thaw cycle is horrid.
I did what Carla does, pretty much, when I lived there. I also took a page from the forum member that Jules mentions. (Can't recall her name off the top of my head.) I wasn't working outside the home very often at that point, but I was spending a lot of time outdoors, walking here and there. And it was not as urban an environment as Toronto -- a bit colder, sidewalks weren't necessarily cleared quickly, etc.
So I faced reality -- for my walking lifestyle, I needed winter boots -- booties just would not cut it. I got some moto boots, combat boots, some chelsea boots with lug soles -- as well as a pair of genuine snow boots. Booties became -- essentially -- indoor wear. Or what I thought of as pure city wear. I'd put on booties if the streets were not terribly slushy/ slick only, and if I was going to be indoors for most time out of the house.
This made it more difficult to come up with outfits I liked, or at minimum reduced outfit variety in the winter.
In my current climate, I aim to buy waterproof footwear. It's just so much more practical. But if I choose unwaterproofed leather (like my new Ecco booties) I spray with waterproofing at start of season and inspect and clean after most wearings. We don't have to contend with a lot of salt on the roads here, which makes a huge difference.
