Daniel and Jason - 17th Street, SF
Daniel: "Mostly what I pick out from other people and mostly just what I see out and about. I really don't have a very good answer."
Jason: "I would say whatever is comfortable and easy to wear. I like loose fitting clothes that I just throw on."
Ah a classic pairing: the prep and the rocker. These guys both do a great job of layering their outfits for maximum SF-weather appropriateness.
I think every guy needs these two types of shoes in their wardrobe. The military boot and the slip-on loafer have a lot of reach, as far as, can work with most outfits in a modern man's closet. (One should add trainers too, because one has to be active once in awhile.)