Sorry if I came across as Snarky, I was shooting for 'tongue in cheek'. As for my winter wear in Toronto I just have a topcoat from London Fog that I got at The Bay for $200. I don't dress up all that often and when I do I'm downtown where I can be strategic and make use of the Path as much as possible so I'm not outside for more than the time it takes to get a cab or cross the street to wherever I'm going for a weekend dinner. But yeah, if you're going to be out much in the winter here you definitely need something warm, including head gear. Fashion wise it's very accepted that you'll see people in toques or heavy hats with ear flaps and such. January and February and even in to March can be painfully cold here.