The Dos and Don'ts of Wearing Over-the-Knee Boots

In the world of boots, the over-the-knee iteration is often considered the most intimidating. As such, we thought we’d go over some general guidelines we’ve gathered from studying how our favorite celebrities and It girls wear the boots well.

If you haven’t yet conquered the statement footwear, scroll down to read our dos and don’ts, check out how everyone from Jamie Chung to Kate Bosworth wears them, and shop some of our favorites!

Chung’s poncho is the perfect way to cover up but still let the boots stand out and speak for themselves.

On Jamie Chung: Alice + Olivia Kyson Draped Poncho ($440) and Dae Over the Knee Boots ($795)

This long coat paired with the tall boots is the perfect subtle look. The boots don’t stand out too much, but they’re also not drowned out by the rest of the look.

On Restoin Roitfeld: Gabriela Cadena dress

Kate Bosworth


Splash News

These Stuart Weitzman boots are a classic. Just the right height, they won’t cut off the natural line of your legs.

On Kate Bosworth: Stuart Weitzman Highland Boots ($798)

Dress up your favorite shirt dress with stand out over-the-knee boots just like Lily Aldridge. We’re inspired.

On Lily Aldridge: Michael Kors dress

Chiara Ferragni


Style du Monde

A pair of bold boots and a simple dress is the perfect outfit combination.

On Chiara Ferragni: Dior boots, dress, and bag

Emily Ratajkowski


Getty Images

Let your boots peak out under a long dress for a covered-up yet interesting look.

On Emily Ratajkowski: Altuzarra top, skirt, and boots; Marli hand chain

Pair your boots with an oversize blazer worn as a dress for a sultry look.

On Roberta Ruiu: Fausto Puglisi dress and boots

Shop our favorite over-the-knee boots: