How to Wear Over-the-Knee Boots Like Jessica Alba, Karlie Kloss, More Celebs

Karlie Kloss wears over-the-knee boots by Stuart Weitzman on Nov. 11 in NYC.
Karlie Kloss wears over-the-knee boots by Stuart Weitzman on Nov. 11 in NYC. Alo Ceballos/GC Images

Want to refresh your boot wardrobe for the fall with the ever-popular over-the-knee-boot? While the style can be a tricky trend to master since they take up nearly half of your body, there is hope!

The boot style has enjoyed a resurrection lately thanks to Stuart Weitzman’s “Highland” and “Lowland” boots, which have become a celeb street style staple over the last two years. As it turns out, the inspiration came from an unexpected muse: Julia Roberts’ 1990 movie Pretty Woman.

“I knew that if I could engineer it off the street corner and on to Main Street, that it would be irresistible,” Stuart Weitzman tells Us Weekly of the footwear, which features a tie in the back. “Thank you, Julia.” 

Since he debuted the high-heeled “Highland” boot in 2013, it has been spotted on every A-list celebrity including Karlie Kloss, Gigi Hadid, Jessica Alba, and Kate Bosworth. His flat boot version, the “Lowland,” made its way to shelves in 2015 and has been equally as popular. But if you’re expecting another incarnation, don’t hold your breath. “It is now available in every height that is wearable. To make it any higher is to put it back on the street corner,” he tells Us. “We have tinkered with our Ozone Layer and look where we are. I am not going to go there.”

Though the thigh-high boots can be intimidating to wear, incorporating them into your daily wardrobe isn’t as hard as it seems. Pulling off over-the-knee boots is all about “playing with the scale of a silhouette,” celebrity stylist June Ambrose, who has worked with Mary J. Blige and Kelly Ripa in the past, tells Us Weekly

Scroll down for Ambrose’s three rules to follow before slipping on the shoes. 

1. Pay attention to leg length

When determining the heel height of your boot, consider your own legs. “The heel version is great for a very curvy girl [since it lengthens the legs], and the flat version is great for a gal with long, lean legs,” Ambrose tells Us.

2. Think about proportions

“I believe in balancing my bold and allowing a punctuation piece such as these to shine,” Ambrose, who has her own line on HSN, June by June Ambrose, says. “I’d style [over-the-knee boots] with an oversize cardigan and silky slip — mixing smart and sexy is a season sensation!”

3. Pair with jackets for an edgy, casual vibe

If you want to wear this type of shoe with jeans, offset the style with a jacket. “Wear [the boots] casually with a biker jacket or a blazer and a tee,” Ambrose tells Us. 

Need more outfit inspiration? Scroll through these celeb street style pics, featuring Stuart Weitzman’s “Highland” and “Lowland” boots!

Jennifer Lawrence - boots
Karadshow / Splash News

Jennifer Lawrence

Jessica Alba - boots

Jessica Alba

Ashley Benson - boots
Robino Salvatore/GC Images

Ashley Benson

Gigi Hadid - boots
TMNY / Splash News

Gigi Hadid

Shay Mitchell - boots
Robino Salvatore/GC Images

Shay Mitchell

Olivia Culpo - boots
Michael Simon/

Olivia Culpo

Bella Thorne - boots
Efren S. Landaos/Press Line Photos/Corbis

Bella Thorne

Would you wear the over-the-knee boot? Tweet with @UsWeekly using the hashtag #stylebyUs!


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