A few years ago I bought my first pair of over the knee boots. I remember thinking I wouldn’t get much use out of them. I was wrong, very wrong. As soon as the chill hits New York, I am reaching for them to anchor generously cut summer dresses for fall, and then pairing them with tights and oversize knits come winter. That’s truly the trick for looking nothing like Julia Roberts in Pretty Woman: don’t wear them with anything tight, unless it’s a maxi with a side slit or skinny pants.
Shop my picks for the 10 best over the knee boots on the following pages!