I've never thought I could pull off over-the-knee boots--I've always shied away from the Pretty Woman undertones--but this picture is making me think otherwise! Styled with a classic striped dress like this one from Velvet, and a chic swingy coat (the one above is by Joie and is 30% off here), the boots look edgy but not over the top. What's also key is the boot itself. The suede pair pictured is by Stuart Weitzman, and perhaps because of their intrinsic greatness, they're sold out everywhere except here.

Photo: Always Judging