I wear:
These boots all the year except when it's too hot, a pair of running shoes specially fitted for my overpronating feet when I'm exercising, and the Birks on this page when it's too hot for boots. If it helps to know what socks I'm wearing, they're purple and black striped with little skulls on them.

Shoe consultant, tell me: am I Doin It Rong or does it just go with my outfit (jeans and a very sloppy hoodie from ThinkGeek, or a flannel shirt.)