Boot season is back, and while there are a variety of shapes, colors and sizes to pick from, we think you should try winter's boldest footwear trend: the over-the-knee boot. While this thigh-skimming boot may bring up memories of Julia Roberts in Pretty Woman, when worn correctly, it looks a lot more street-styled than street walker. And speaking of street style, we've got 6 looks that will help you to overcome your fears and try the trend this season. Click through to get inspired.

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