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Maxi skirts are one of my favorite things to wear in the cold weather. I usually wear thick leggings under them for warmth. I often wear riding boots if I want a casual look, or else I wear dress boots with a heel for a more dressed-up look. I'm sure you could wear booties too.
Agree with Gigi, the tall boots with leggings or warm tights is a classic look. The hostess at a holiday party I went to last year wore a maxi skirt, flat tall boots and a pretty silky blouse. She was one of the most elegant women there