Tim Gunn's Rules of Style

The Project Runway mentor and fashion guru answers all your style conundrums.

By Tim Gunn

August 4, 2011 12:00 AM
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Over-the-Knee

"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!

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