I spent years thinking that what I wore on my feet through the winter didn't matter much...then last year I decided to buy a pair of decent boots and they made a world of difference. The problem with upstate NY is that the weather varies quite a bit, so you deal with a lot of slush (which means wet feet). The way I see it, there are two ways to go: 1. Buy one pair of boots that work for all winter days. This would be something that comes up at least 6" on the ankle, is waterproof, looks good, and is preferably insulated. Your best bet here is most likely something from Red Wing. 2. Buy two pairs of boots; one that's a bit less winter-oriented (maybe Desert Boots and thick socks) for the dry days, and something very purposeful for the storms and slush (Sorels, maybe?). That's my take, anyway.