hey all, quick question. I'm pretty ignorant when it comes to fashion , not necessarily terrible at it, but admittedly pretty lazy.
I'm looking for winter(ish) shoes or boots whatever to go with a reasonably casual look. in the winter I'll usually be wearing charcoal/stone colored chinos + a sweater like this if its not too cold:
http://factory.jcrew.com/mens-clothi...olor_name=navy
currently Im just wearing Sperry topsiders which are obviously a summer shoe. so I need to get something for the winter. I live in Chicago, so it rains and snows. feel free to quote things across a wide price range, though since my eye for fashion is pretty bad anything too expensive will likely be outclassing the rest of my wardrobe. thanks
also, I guess I need a jacket. (currently just have a std northface zip up). Happy to take suggestions on that too