I believe the trick to making over the knee boots not appear to be hookerish a la Pretty Woman is to go with a flat boot and not a stiletto. Flats give it a more casual feel and will pair great with leggings, skinny jeans AND dresses. My husband was texting me furiously the other day because he saw someone on the street in downtown DC with over the knee high heeled boots on and a super short dress. He told me he was not a fan of the trend and thought it was inappropriate. When I talked to him about other options and how I’d wear flat over the knee boots, he was a bit more open to the idea.
I like these boots because they’re versatile, you can wear them above the knee or you can cuff them to make them more casual. I’m torn between the black or the cognac brown they have. All I know is that I’m dying to try a pair on. Have any of you tried over the knee boots yet? Send me a picture or let me know what you think of them!