I don't know what your budget is but i would suggest just getting a GOOD store to take care of you over the long term.
For me (I am 26 and i like to think relatively hip - just for perspective, like i am not 40), i go to 'Ed Williams' up in Crowfoot Crossing behind the KFC. It SEEMS like nothing but when you go in they have AWESOME stuff for the modern man. Wicked sport coats, custom shirts, good shoes, etc. It is not cheap but it is not outragous for what you get either. You can literally feel the difference in your clothing. You feel more confident and that translates into success. You cannot find this kind of feeling/stuff at Moores or Brogue Man or whatever...
Go there, even if you are not intending to buy anything, and speak to 'Thomas' (there except on WED). He will take care of you. He is young'ish and is very willing to explain what you should and shouldn't do with your wardrobe without pressuring you to buy. And he will also give tips on how to 'build your wardrobe' cost effectivily with the right peices so you can maximize your money.
I can also tell you he did up an entire new wardrobe (more $$$ then i care to know) for a certain unamed Calgary Flames player....
HIGHLY recommended.
Claeren.