Fashion and winter can get along just fine and there are great examples of people who utilize this right here in Winnipeg. All you have to do is take a simple walk at the University during the break between classes to realize that there are large amounts of people with great style even during some of the, or at least what used to be, the coldest months of the year. I think we can all take fashionable tips from the Asian community most notably, because they definitely have a keen eye for what looks good without sacrificing warmth (most of the time).
I think it really depends on where you go if you want to determine if what people are wearing is fashionable or not. I don't think you can classify an entire cities fashion sense based on individuals in specific areas along busy thoroughfares. You urbanites should head to a suburban mall, educational institute, or office park. Then you'll see what you would call "fashionable" individuals.
