Getoutside shoes is an awesome store! The Queen Street located is their original location (they recently opened a bigger store on Yonge Street, South of the 401). They have a lot of cool, different shoes - shoes that you won't be able to find at your local mall. From Converse, Puma, Ben Shurman, to Tretorn and everything in between. I bought a hard to find pair of Tretorn rainboots there.
They have a pretty good supply of Converse (chuckies) as well as an ample supply of rainboots. There's a few shoe stores along the south side of Queen, so I'd hit those up as well (this one being one of the last two before you hit Spadina - if you're heading west bound).
You can shop online and there's free shipping within Canada, so it's good to take advantage of that - if you don't mind waiting for your shoes.