Sounds crazy coming from me, but I gotta say that I don't love the shearling in that fit. Great piece of course, and I'm sure you'll love it next winter (where the hell are you that you can still wear that?), but the pants and hat want other outerwear I think.
Well, possibly that or something similar. but again, them kind of sneakers I dislike, or even anything remotely related to them, so I wouldn't really know what would go best with them. But with a functional looking sweater and dark jeans, a pair of, even, solovairs, would be in keeping with the practical look up top.