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6 Ways to Show Off Your Over-The-Knee Boots with a Skirt

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Let’s just get this out of the way: Yes, Pretty Woman featured Julia Roberts working the corners of Hollywood Boulevard in a pair over-the-knee boots with a skintight cut-out dress and, no, we don’t endorse trying the same ensemble beyond Halloween. But after logging several, infinitely more respectable years on the runway and street style scene, the thigh high design has clearly redeemed itself. Where pre-Rodeo Drive makeover Vivian gave you one bad way to wear it, fashion can offer up dozens of chic and sophisticated alternatives.

Our favorite option of the moment? Teaming super tall footwear with skirts of all lengths (even short ones—more on that below!) in lieu of tights, especially when the two pieces contrast in an interesting way. Think of a lace and embroidery-clad Cara Delevingne on her Suicide Squad tour, her famously long stems encased in black suede, or Selena Gomez in March of 2015, who updated the old school denim mini by swathing two thirds or her legs in stretchy black fabric. Now it’s your turn to get in on the action! Scroll down for 6 skirt and over-the-knee boot formulas that feel so right now.

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