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Try Ernie's Shoe Repair on Kingsway and Earls. An old Chinese guy runs the place and he knows his stuff. It cost me about $30 to get a pair of loafers re-soled and re-heeled.
For dress shoes, definitely invest in at least one classic pair (Oxfords, wing-tips/brogues, etc.) of leather-soled shoes. If you take care of them, they'll last a long time.
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