I Found All the Best Stretch Boots in Every Height

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

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.
-
Move Over, Jeans—The Chicest People I Know Are Wearing This Expensive-Looking Pant Trend With Boots
Spotted on Naomi Watts.
-
My Mom's 63, I'm 29, and We Both Love Zara and Madewell—Here Are 33 Pieces We're Both Eyeing RN
They're ageless, timeless, and modern.
-
These Are the Surprising Shoe Trends Gen Z Is Styling With Everyday Outfits for the Rest of 2025
Niche, weird, and unconventional.
-
Forget Flats—Everyone With Good Taste Is Wearing These Boots With Jeans and a Jacket
Put these on your shopping list.
-
If You Only Have $200, These Nordstrom Shoes, Handbags, and Accessories Will Get You Endless Compliments
Everything included is on sale, too.
-
I’m a Senior Shopping Editor—These Elevated Yet Affordable Nordstrom and Old Navy Fall Picks Have My Attention
Just about everything is under $100.
-
I Need New Eyeglasses—These Are the 30 Cool-Girl Pairs I'm Considering
Looking for a new signature look?
-
I'm Shopping for Sweaters, Shoes, and Jackets From Nordstrom's Epic Fall Sale—Here's What's in My Cart
Up to 50% off.