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. Between knowing what hemlines to wear with them to figuring out how to wear them with jeans, it’s enough to make someone just avoid the style altogether and just put on a pair of ankle boots again. But since that would be a shame, we thought we’d go over some general guidelines we’ve gathered from studying how our favorite celebrities and It girls wear over-the-knee boots so well. If you haven’t yet conquered the popular statement shoe style, scroll down to read our dos and don’ts, check out how everyone from Emily Ratajkowski to Kate Bosworth wears them, and shop some of our favorite styles.

Dos and don'ts of how to wear over-the-knee boots
Lily Aldridge
Lily Aldridge Over-the-Knee Boots


Timothy Hiatt/Getty Images for Michael Kors

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

On Lily Aldridge: Michael Kors dress

Chrissy Teigen
Chrissy Teigen Over-the-Knee Boots


BG024/Bauer-Griffin/GC Images

Chrissy Teigen’s long coat makes a statement, and the over-the-knee boots and skinny jeans complement it and make for the perfect chic silhouette.

On Chrissy Teigen: Chloé Layered Houndstooth Wool Trench Coat ($2070); Saint Laurent tote; Citizens of Humanity Rocket Skinny Jeans ($218); Saint Laurent boots

Emily Ratajkowski
Emily Ratajkowski Over-the-Knee Boots


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

Julia Restoin Roitfeld
How to wear Over-the-Knee Boots


Stephen Lovekin/Getty Images for Gabriela Cadena

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 Julia Restoin Roitfeld: Gabriela Cadena dress

Kate Bosworth
Kate Bosworth Over-the-Knee Boots


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 boots

Chiara Ferragni
Chiara Ferragni Over-the-Knee Boots


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

Roberta Ruiu
Roberta Ruiu Over-the-Knee Boots


Elisabetta A. Villa/WireImage

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

On Roberta Ruiu: Fausto Puglisi dress and boots

Shop our favorite over-the-knee boots:

This post was originally published at an earlier date and has since been updated.

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