My vote is to wear them with skirts rather than over jeans or leggings - skirts that are long enough that until you sit down, it's not obvious that you're wearing an over-the-knee boot. Also, I would suggest avoiding overly shiny leather and too much of a heel. As I have pointed out on another thread, once you go shiny and heeled, you're in the poster for Pretty Woman.
The ones I have from Stuart Weitzman (I think they're the Lowland style) do need to be retied periodically. They have satin on the inside and start slipping down even when tied snugly.
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