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.
Impressively, the Princess of Wales has been wearing these specific boots since 2004. Yes, really. She clearly can’t get enough of her Penelope Chilvers Standard Tassel Knee High Boots ($695).