"I love the over-the-knee boot trend. The problem: I don't know how to wear it without looking like a hooker! I'm in my mid-30s short shorts and miniskirts are just too daring for me, but that's what they're styled with most often. Any alternatives?"
Over-the-knee boots present a styling challenge. We're used to seeing them with minis and shorts, but I find they can look great with asymmetrical shapes because you have the compromise of a longer/shorter effect. They can also work with longer hemlines, providing the skirt has a slit that reveals the boots' higher length when you walk or sit. Otherwise, why bother? I also find that a flat boot presents more options because it can function very much like a legging. In fact, that should be your guide: Whenever you would opt for leggings, ask yourself whether you could substitute over-the-knee boots. I'm quite certain that your answer will be yes!