Living in Toronto, Canada, I am envious of San Francisco weather. It rarely ever rains here and there isn't a need to deal with snow, either. However, it does get cold enough where jackets can come in handy- but not too cold.
During the winter, I keep my Allen Edmonds within the safe confines of my closet. I rarely bring them out, knowing that it may snow, hail or rain. I do have a few pairs that have rubber soles on the bottom and I can confidently wear them on days where the weather will not be coming down. Otherwise, boots and throwaway top-grain/corrected grain shoes with glued-on rubber soles come in handy.