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I think your budget screams Sears.
I don't know if it includes Montreal, but I've found this GQ list has very high quality boutiques:
http://men.style.com/gq/features/gq100
If you have time but not money, go to a Century 21 or Daffy's (or its equivalent outlet/possibly-imperfect store wherever you are) and sift through things there. Do note, that it takes a lot of time and patience to find anything good at those stores.
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