The 27 Best Stretch Boots That Are Editor-Approved

last updated 11 November 2023

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The thing I look forward to the most when fall is on the horizon is getting to take my boot collection out of hibernation. Whether with a pretty dress, a chunky sweater, or my favorite jeans, boots are a ubiquitous addition to just about all my fall outfits. For many years, great stretch boots have been on rotation in my closet.

Thankfully, not only do this season’s offerings of the popular stretch design come in a variety of heights, but there is also an option for just about every personal style. I rounded up 32 of the best picks online, which include every height, from over-the-knee to ankle to statement thigh-high, and each offers a different take, whether it's in the form of heel height, sole thickness, toe shape, and more. My favorite? Black over-the-knee boots with a lug sole. Scroll on to discover your own top pick for fall below.

Over-the-Knee Options

H&M

Tall Boots

I would have never guessed that these over-the-knee boots are under $100.

Proenza Schouler

Faux Leather Over-the-Knee Boots

These are the exact boots Camille Charrière is wearing above.

Raye

Nolia Boots

Suede boots are perfect for fall and winter outfits.

Valentina Rangoni

Assia Over the Knee Boots

This style would look great with a skirt.

Steven Madden

Tanzee Boots

The sculptural heel makes these stand out.

Song of Style

Dani Boots

I can see myself wearing these boots for many years to come.

Stuart Weitzman

Lowland Ultralift Over The Knee Boots

These lug-sole boots are fashion-girl approved.

Zara

Over-The-Knee Fabric Boots

These are 100% party boots.

Silent D

Zeno Over the Knee Boot

A classic.

Knee-High Options

Gia Borghini

Stretch Knee High Boot

So sleek.

Steve Madden

Roxanna Knee High Boots

These also come in white and a cool black-and-green option.

Franco Sarto

Katherine Knee High Boots

Here is a classic take on knee-high stretch boots.

Wonders

Tall Stretch Boot

These will brave any weather.

Silent D

Comess Knee High Boots

Chocolate-brown boots deserve a moment in the spotlight this season.

Amy Crookes

Lucienne Floral Print Shirred Stretch Boots

These have Scandi girl written all over them.

& Other Stories

Heeled Knee High Leather Boots

Square-toe shoes are some of my favorites.

Valentina Rangoni

Leonida Strech Tall Boots

I love the peekaboo blue heel.

Wetkiss

Platform Knee High Boots

A mega platform is on-trend this season.

Ankle Options

& Other Stories

Suede Sock Boots

I can see these boots with everything from printed dresses to straight-leg jeans.

H&M

Leather Ankle Boots

Effortless boots always have a place in my closet.

Agl

Tiggy Sock Booties

I'm a huge fan of creepers, so these are right up my alley.

The Drop

Jane High Heel Pull-On Sock Boots

One reviewer called these "incredibly comfortable and nice looking."

Stuart Weitzman

Audrey 75 Stretch Bootie

Extremely worth the investment.

Mango

Heel Sock Boots

These edgy pointed-toe boots are giving me designer vibes.

Vagabond Shoemakers

Cosmo 2.0 Stretch Boots

Here is another great lug-sole option.

Zara

Fabric Heeled Ankle Boots

Under $50 and super versatile? Yes, please.

Stella McCartney

Platform Stretch Boots

I am obsessed with the chunky sole.

Next up: I Swore I Wouldn't Buy Anything New for Fall—7 Outfits With Stuff I Already Own

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Jennifer Camp Forbes is a senior shopping editor at Who What Wear, where she has worked in a variety of capacities including creative director and various editor roles. She’s a well-known shopping expert that’s sought out for advice and insight on the latest trends, outfit ideas, and fashion picks thanks to her thoughtful shopping roundups. Jennifer's lifelong interest in fashion led her to intern at Harper’s Bazaar as an undergraduate. Later, while working towards her masters degree in psychological counseling at Columbia University, she founded two digital fashion publications: Le Fashion and Olsens Anonymous. The popularity of both sites grew and after graduation she decided put her plans to become a therapist aside to pursue a career in fashion.