My DS is pretty young, not in school or anything, so he doesn't need Gym shoes, etc. He has one pair of everyday shoes which are usually some kind of sneakers, and then when seasonally appropriate a pair of sandals, rain boots, or winter boots. I don't get him dressy shoes because I figure on the rare occasion that we need to dress up for something it doesn't really matter if the 2 year old is wearing sneakers, kwim?
*Insert list of crunchy mom stuff here*
ISO Zutano and a Ponyo DVD, IHA 2t Antsy Pants and size 1 Piddle Poddle trainers