I finally read something that made me realize why I just can't buy into the idea of over-the-knee boots. It was in the September issue of InStyle, a page about boots. In the "Trend Alert" section, they highlighted OTK boots. But what they said about them will ensure that I will never, ever attempt to wear that trend:
"Last seen circa Pretty Woman..."
Of course they went on to say that proper people can wear them now, but I can't get this image out of my head.