i live in manhattan, a city many consider much more fashion forward than montreal.
i get by on levis and sneakers all the time. i see it everywhere in the city as well. (i usually rock adidas or pumas, however. never thought they were "dressier shoes.")
true, you have some guys who drop $300 on seven jeans, but few chicks i know who are into straight men really give a fuck, let alone mark anyone down for wearing a $45 pir of levis.
i've never been, but i find it a little odd, that you canucks think there's a certain level of dress that suit montreal standards. it's fucking canada, for crying out loud!
I visit Manhattan every summer (and have for the past 7 years--it's my favorite city), and I can tell you without a doubt that the "average" guy in Montreal dresses a million time better than the average guy in NYC. No contest. You have many, many more wealthy folks, though, so there are considerably more
extremely well-dressed dudes walking around in NYC.
Have also visited Paris, Rome, London, etc. numerous times. A case can be made for any of these cities being more fashion forward than Montreal, and I suppose that on the high end New York smokes Montreal, but on average, again, there's no contest.
As for Canada--we're not like the rest of Canada, here. I was born and raised here, and I don't identify with Canada at all... so say what you want.