Being a fairly practical sort of person, I tend to be a bit annoyed by the impractical boots I see around town. (By impractical, I mean ill-suited to wintery weather, such as snow or ice.) For example, I find myself baffled by knit boots. What happens when they get wet? Other than, you know, frostbite or trench foot. Boots with high or wedge heels bug me too, because when the sidewalk is slippery, a high-heeled boot isn't likely to do you any favors.
(Not that my no-heeled, Vibram-soled boots -- see below -- did me much good last Friday, when Madison was hit by freezing rain in the late afternoon. I was walking through the church parking lot a little after 6:00 p.m. that evening, and the was so slippery that I actually started sliding backwards when I encountered a modest upward slope. But it would have been even more treacherous with high heels.)
I do like ugg boots. I know a lot of people think they're ugly, but for the most part I like the way they look. (This may be due to my lack of any sort of fashion sense, though.) I say "for the most part" it's really only the classic style I like; the ones with external shearling stitching or buttons or faux fur, no thanks. I'm not wild about the one with colored leather, either, but the color bothers me a lot less than the frippery.
For my nickel, I like hiking boots. Not that I do much hiking per se, but I do walk a fair amount, and I like the arch and ankle support they offer. I'm currently wearing a pair of Merrell Moab Mid Gore-Tex boots. For winter wear they work pretty well, because they're waterproof and they've got nice thick Vibram rubber soles with good tread. They're not particularly warm, but that's nothing a second pair of socks can't fix. They don't look much like boots, though. I remember one time I complimented my young friend Lola on the boots she was wearing, and invited her to admire mine. "Those aren't boots," she scoffed. "Those are sneakers." I tried to convince her, but I think she thought I was trying to trick her.