How To Wear: Thigh High Boots (Without Looking Like A Hooker)

We, much like the rest of the even vaguely fashion-y world, are rather obsessed with thigh high boots for fall. (And speaking from experience—I got my first pair of thigh highs two years ago—I can tell you they’re as bitchin’ in real life as they are on the runway.) The thing is, all that gloriousness can be a little challenging to reign in. And when it’s not correctly executed, you will look like a hooker. (Think Julia Roberts in “Pretty Woman.”) Because we love you and want to help you avoid being propositioned by dirty old men in bars, check out our tips for styling thigh high boots.

• Opaque black tights are your friend. Possibly your best friend, even. Buy several pairs for your new thigh highs. There’s something inherently trashy about such tall boots that display a few inches of skin between them and your skirt.
• This is not to say that they won’t look awesome with a tight, short, high-waisted pencil skirt. You just need to invoke the above opaque tights rule and go with a pair of thigh highs that are highly fitted. As for skirt length, it should overlap with the top of the boots for at least an inch. Shorter than that and someone’s going to offer you ten bucks for a hand job.
• Recycle the floral dresses you brought for summer with your thigh highs, a cropped leather or denim jacket and, you guessed it, opaque tights.
• If you insist on wearing jeans with thigh high, they best be super-fitted throughout. Like these.

And, FYI, these boots are $80 [MIA, Zappos.com].