How to Wear Thigh-High / Over-the-Knee Boots

Tricky, tricky, tricky – over-the-knee boots, that’s what they are.

Although boots that go up to there were predicted to be a major fall 2009 shoe trend, it looks like they’ll still be around until the first half of 2010. This means it’s time to take out the ol’ Stairmaster.

So how do you wear over-the-knee boots and exude haute couture instead of hooker chic? We’ve compiled some celebrity looks that would totally work and some that might prompt sleazy guys to ask what exactly is your line of “work”.

We’re Not So Sure…

L to R: Hayden Panettiere, Rihanna, Kelly Rowland and Ashley Tisdale

Hayden Panettiere: Over-the-knee boots don’t work on all body types. They highlight the thickest part of the thigh and Hayden Panettiere has the misfortune of picking a pair that doesn’t do justice to her petite frame.

Rihanna: We all know that fishnet stockings should never be paired with over-the-knee boots. But how about boots that are made to look like fishnet stockings? Kind of a 2 for 1 deal? Um – no. Still doesn’t look good.

Kelly Rowland: She looks good from the thigh up but her over-the-knee boots in shiny patent leather cheapens her entire look.

Ashley Tisdale: Don’t know if it’s just the angle of the shot but Ashley Tisdale’s boots look like they don’t fit her. They bunch up and make the svelte starlet look like she has bigger ankles than she actually does.

We’d Put Ourselves in their Shoes…

L to R: Lea Michele, Blake Lively, Hilary Duff and Gwen Stefani

Lea Michele: The Glee actress hits all the right notes with her over-the-knee boots. They fit just right around the thigh and the knees and has the perfect amount of slouch around the leg.

Blake Lively: It’s easy to wear over-the-knee boots when you’re as tall as Blake. The Gossip Girl main star keeps it cool and casual by pairing her boots with a plaid peacoat and a brown leather bag.

Hilary Duff: Keeping everything in proportion here – Hilary Duff balances her skintight over-the-knee boots with an oversized tee and big accessories.

Gwen Stefani: It’s difficult enough to pull off over-the-knee boots but high-heeled over-the-knee boots? It’s suicide. But Gwen Stefani shows us that by keeping everything else covered, it can look so fashion forward. Having a sparkling personality like Gwen’s wouldn’t hurt either.