Wingtip ankle boots: from a footwear standpoint, about as dressy as you want to be if your day might involve trudging through snow. They work with denim and you can wear nicer specimens with worsted suits, but the sweet spot is clearly a pairing with your coarsely textured wool flannel or tweed trousers. Ideally you want either a heavy rubber tread or a leather sole that your local shoe repair shop can easily winterize. As the four boots we found here clearly demonstrate, you get what you pay for in terms of quality and finish. Shown: Florsheim [$150], Massimo Dutti [$225], Loake [$440 at East Dane], To Boot New York [$450 at Nordstrom].