One thing that bothers me in the winter...
People who want to wear open toed shoes...but not outside so they bring two pairs with them.

I don't get it! If you toes are going to freeze don't wear those stupid shoes in the dead of winter in Montreal!
Just because its winter doesn't mean you have to cover yourself up completely. When I go out, I'll wear a mini skirt, with a nice top *even a dressy tank top if it looks right* nice long boots and a coat. The reason i don't care to be in tanks and mini skirts is because I have a car! The most I will be outside is....walking from my parking spot to the place I am going. When going to Xmas parties and things of that sort you hope there is valet parking or have someone drop you off in the front.
Whats really annoying? People who do wear the mini skirts and then complain that they are freezing while waiting for a bus to come along. If you are going to be in the cold for long periods of time, I don't recommend bareing all.
Just make sure you dress up for your climate and things of that sort.