I live in New England, so we know winter, too, but I never wear " dress" boots. They'd get ruined in the snow and slush. Plus, my legs are long and my feet are long and narrow...finding shoes is a challenge, never mind boots. I have several pairs of snow boots, and I change into shoes once I get to work. If I'm going out to eat or shopping or something, I just wear the snow boots. On my days off, if the sidewalks are clear, I wear my Topsiders.

GF - I am a boot girl. I run cold and I like to be comfortable and warm. I also wear leggings a log so tall boots work for me. The first three are my cold weather/snow boots (Uggs belcloud, adirondak tall, adirondak) very comfy and warm. I have the Uggs cortona and Aquatalia Undy for dress. My charles David regiment boots are fab but not insulated and are fall/spring only. I find boots easier to fit for me than shoes (I don't really own shoes - just boots and booties) Also my merrell encore ice clogs are fleece lined and toasty with socks for hanging out at home if I don't want boots. It's what you love that's comfortable - but that's what works for me!!

Yes, because I wear skirts & dresses a lot and run cold.

Yes - and not because of weather, but because I've always liked the look and they work so well with skirts on the rare occasion that I wear them. I have a pair of black Cole Haans that I love. They add the right amount of polish to my skinnies/boots look or skirt/boots look.

Nope. Tall leather boots are not warm enough for me for real winter (below freezing) for either the foot or the shaft. If the snow is deeper than 5 or 6" (15cm) I wear snow pants with mid-calf snow boots, adding waterproof gaiters for skiing/walking in snow.