You can go with a nice pair of Doc Marten's in the Wellington style of boot. It's a pull-on, has lug soles and is a very comfortable fit. Good for cold weather riding and knocking around town with jeans. I use a brown soft-shell ski type coat from .511 Tactical. No wind gets in while motorbiking or skiing. I got one a size larger than I usually wear so I can layer if needed. The coldest I've ridden in so far was 17F, and was wearing my soft shell over a golf wind shirt and a long sleeve T. Warm as toast. And before all you Yankees go on about how much colder y'all ridden in that beats my measly 17F record, notice that I live in Baton Rouge, Louisiana, which is located in the sub-tropics and not in the frozen nawth. We ride year-round down here.