Insulated hiking boots in the winter, skate or running shoes in the summer. If it's raining, I wear uninsulated Gore-Tex hiking boots. You don't need stiff soles if you're riding BMX or other wide platform pedals, that's a clipless thing.

I don't know how much luck you're going to have finding a waterproof shoe that looks office casual. Maybe booties over your work shoes on rainy days would be a better bet.