I just posted a thread asking about Red Wings, so will definitely keep tabs on this thread if there are any comments on them!
I guess I'm in a similar predicament to you so I'm not too sure how much I'll be able to help. Are you going for practicality? Because I think a hiking style boot would look great as well as endure the harsh winter! Can't think of a much better casual look than some indigo jeans with hiking boots for the winter. Although I've heard steel-capped boots can be a pain when it comes to wearing away the front of your socks though