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Another vote for Allen Edmonds. I have three pairs of them and they've lasted me over ten years of everyday use with numerous resoles and reheels, of course). I really liked the wingtips made by Hawthorne Classics, but I think I heard they went out of business.

Oh, and Andrew Markworthy's advice way above about stuffy rooms was particularly good. Some of your first suits (even though you're in Toronto) should be lightweight--ask for 'tropical weave'--for this very reason. You can always slap a coat on outside, but it makes a poor impression to be...

Max's advice is good. The tailoring can be worth more than the suit, if you've got a good tailor. Stay away from the Armanis while you're building your suit collection. Once you're pulling in the 6 figures you'll be able to do all the Armani you want, but no sense promising what you can't...