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How to Wear Over the Knee Boots (without looking like a Pirate)

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Over-the-knee boots can feel intimidating. Here is how to wear them without looking like a pirate!

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Get a Pair with Heels

Boots with a heel

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First, this is non-negotiable for me. Heeled over-the-knee boots have structure and shape that helps them stay up better.

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A Heel Adds Versatility

Heels = Versatility

Heels avoid that "pirate boot" slouch that can happen with flat boots. The heel also gives you more styling versatility—you can wear them with everything from jeans to dresses.

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Make Sure They  Stay Up

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Boots stay in place

The whole point of over-the-knee boots is that they stay over your knee. Look for boots with some stretch or grip at the top.

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Choose the Right Color

Color matters!

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I stayed away from black boots for the casual outfit and went with cognac brown instead. This makes the boots stand out without overwhelming the look.

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