The Princess of Wales and Jennifer Lopez might not have a lot in common, but they certainly share a love of knee-high boots. Both women regularly wear the trend every fall and winter, offering up a plethora of outfit ideas that are ripe for copying. In Kate Middleton’s case, she’s been wearing one specific pair of knee-high boots for nearly 20 years: Penelope Chilvers Standard Tassel Knee High Boots ($695). If that doesn’t prove that the style has staying power, I don’t know what will.
Below, I rounded up my favorite examples of Middleton and Lopez wearing knee-high boots and included pieces you can shop to re-create their looks. There’s an outfit here for nearly any occasion, including a casual weekend look and a dressy option for the holidays. Scroll down to learn how to style knee-high boots.
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