In 2002 I purchased my Favourite Pair Of Shoes Ever™ at Getoutside, but I've worn them so often that the brand name is completely rubbed out. They're black leather with a beige rubber sole, sort of like Asian ballet slippers with laces, and I've never been able to find a similar pair since. Getoutside no longer stocks shoes even remotely similar to this style - they've since been replaced by an obscene number of Vans, Converse high tops, Clarks and Hunter rain boots. I wish they still sold these shoes because I would buy 10 more pairs - most comfortable shoes ever.
The website describes their staff as "friendly and energetic" - I wouldn't call them UNfriendly or lazy, but I would never describe them as the former. They're just standard shoe store employees. More often than not you have to approach them for help because they're busy talking to each other instead of observing their clientele.
If you're looking for a pair of trendy, modern style shoes I'd recommend hitting up Getoutside and Groovy, both on Queen Street east of Spadina.