Warm through the winter. Cute. Comfy. Snuggly. Flat. Love them. Not the most practical in things like snow, but I wear 'em whether I'm gonna slip and die or not - least I'll go out with lovely looking, warm legs.
I think that it would be a tie between my hiking boots, Converse, and Vibram FiveFingers. I might go with the latter of the three, though, to keep my feet strong and in shape if ever they wore out and I had to go barefoot, hah.
My red vans. They're good for walking but they don't look stupid with regular clothes like gym shoes do. Plus, they match all of my outfits since I'm a psychopath. But I would certainly miss my white flats and my sparkly red heels.