How to Style Knee-High Boots Like Kate Middleton and Jennifer Lopez

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).
This one's perfect for dressier occasions. A beautiful plaid midi skirt is a great match for a pair of suede knee-high boots.
A striking red coat is always a good idea. You're sure to garner compliments aplenty if you copy this Kate Middleton outfit.
Believe it or not, the holiday season is not too far off. This is the perfect party look for just about any soirée this winter.
Plaid and fall go together like peanut butter and jelly. Copy Lopez and try an oversize plaid jacket with your favorite knee-high leather boots.
Last but certainly not least, this is a great option for transitional weather. The dress is clinging on to summer, but the boots are absolutely ready for fall.

Erin got her start as a Who What Wear intern in 2011—back when the site only published a single story per day. (We have since increased that number twentyfold.) She graduated magna cum laude from USC and lives in Los Angeles. In college, she also interned at Refinery29, where she was promoted to editorial assistant and then assistant editor. After nearly three years at R29, she came back to WWW in 2015, where she is now the Associate Director of Fashion News. From the Oscars to the Met Gala, she leads the site's entire red carpet coverage strategy. She specializes in celebrity and fashion news but also enjoys writing travel features and runway reports. She frequently contributes to WWW's social accounts and has a sizable following on her personal TikTok.