How to Wear Over-the-Knee Boots (Without Looking Trampy)

Sure, there’s a certain Pretty Woman association that can’t be escaped, but the reality is that over-the-knee boots are extremely wearable. Here’s how I pull off this runway staple without looking like a catwalk catastrophe (plus, my favorite picks for this season):

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Keep it simple.

If you’re a little timid, ease into the look by keeping the rest of your appearance understated. A pair of dark jeans and a lengthy cardigan give you a fall-chic look that balances