Originally Posted by fait accompli
T-shirts and shorts are good enough if you're in Toronto, It's not all that much worse there than florida.
Seriously, all you really need to make sure is that you stay dry, so you need to ban cotton for all winter when you go outside because when it's wet, it will stay wet. So NO cotton socks, t-shirts, jeans... What works really well is get some polar underpants/shirt (polyester material) from Mark's and then wear something not that hot on top. The polyester will allow you to stay dry and hot, the rest is just extra layers. I've been doing that for a few years now, and it's really good.