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.



Lily Aldridge
(Image credit: 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
(Image credit: 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
(Image credit: 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
(Image credit: 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
(Image credit: 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
(Image credit: 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
(Image credit: 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.

Editor in Chief

Kat Collings has over 15 years of experience in the editorial fashion space, largely in digital publishing. She currently leads the vision for editorial content at as the site's editor in chief, having risen through the editorial ranks after joining the company in 2012. Collings is a Digiday Future Leader Awards nominee, was named Buzzfeed's best fashion Instagram accounts of the year, and is a member of the CFDA Awards Fashion Guild. Prior to Who What Wear, Collings worked on styling projects for brands such as Vogue, Teen Vogue, Lucky, and Oliver Peoples. She graduated from UCLA with a BA in communications and calls Los Angeles home.