Photo Courtesy of Sam EdelmanKnee-high boots are no longer just a fall staple—they’re a runway obsession, and October Prime Day has the season’s most stylish pairs marked down.
Whether you’re team equestrian leather, slouchy suede, or glossy croc embossing, these boots are proof that tall silhouettes are the power move of fall 2025. Style icons have shown us exactly why: Princess Diana wore hers with tailored blazers and cigarette jeans, while Carolyn Bessette-Kennedy paired hers with pencil skirts that still feel impossibly modern.
Designers even agree, Miu Miu reviving second-skin fits, Burberry reimagining the riding boot, and biker boots still commanding attention post–Fall ’22. What makes them irresistible is their range: they’re just as effortless with bohemian maxi dresses as they are sharp with suiting.
The best news? October Prime Day prices mean you can shop runway-level boots without the splurge. Consider this your invitation to make tall boots the centerpiece of every fall look.
The Best Knee-High Boot Deals for Fall:
Coutgo Wide Calf Knee High Boots
Finding stylish, comfy boots on Amazon can feel like a gamble, but these are a major win. Reviewers (and editors) rave about their fit, quality, and wallet-friendly price tag.
Sizes Available: 5-11
Colors Available: 5
Eteridrey Chunky Brown Knee High Boots
Try the Y2K comeback with these under-$40 brown suede slouchy boots. They pair effortlessly with everything from fitted pants to dresses.
Sizes Available: 7-10
Colors Available: 3
Sam Edelman Sylvia Knee High Boot
A sleek silhouette, glossy finish, and dreamy color options make these boots look way pricier than they are. Bonus: They passed the subway-step test and impressed our wide-calf editor with their perfect fit.
Sizes Available: 5-13
Colors Available: 30
Steve Madden Smith Knee High Boot
These stiletto boots look runway-ready with their sleek colorways and rich leather finish. Save them for evenings out—they’re made for making an entrance, not running errands.
Sizes Available: 5.5-11
Colors Available: 2
LifeStride Gracie High Heel Boot Knee
Wide-calf shoppers, meet your new holy grail boots: they’re sleek, stretchy, and shockingly affordable. Plus, the mix of materials gives them a polished two-tone finish you’ll love showing off.
Sizes Available: 5-12
Colors Available: 5
Naturalizer Fae Knee High Boot
Suede boots are having a major moment, and this Western-inspired pair is the fall essential you’ll actually wear everywhere. The chunky stacked heel is comfy enough for all-day strolling, and the ankle zipper makes them super easy to slip off.
Sizes Available: 5-12
Colors Available: 7
Dr. Scholl's Shoes Brilliance Wide Calf Riding Boot
Classic riding boots, comfy insoles, and a low heel make these Dr. Scholl's boots a wide-calf staple. Reviewers say they’re easy to wear all day long—just size up for the best fit.
Sizes Available: 6-11
Colors Available: 2
Modatope Knee High Boots
Make your fall wardrobe pop with these statement-making burgundy boots. Trendy square toes and a knee-high cut give instant style cred.
Sizes Available: 6-11
Colors Available: 17
The secret to scoring the best October Prime Day deals? Being an Amazon Prime member! Find out how you can join for free now.
When is October Prime Day?
Amazon October Prime Day 2025 runs from October 7 through October 8. This 48-hour sale begins at midnight PT on Oct. 7 and ends at 11:59 PM PT on Oct. 8. This year shoppers will be able to find extensive discounts on products ranging from summer fashion and premium beauty to the newest electronics and home essentials . There are early deals leading up to the sale, so it's wise to check for pre-Prime Day offers as well. Officially, this sale is known as Prime Big Deal Days, and it is commonly referred to as October Prime Day.
What is on sale for October Prime Day 2025?
For October Prime Day 2025, Amazon is offering a wide range of deals on seasonal must-haves across multiple categories. Shoppers can score discounts on fall fashion, holiday gifts, Prime Day beauty deals, and more. Whether you're looking for tech upgrades, home essentials, or trending products, October Prime Day 2025 promises unbeatable savings and exclusive deals on all your favorite items.
Join Amazon Prime
Amazon Prime costs $14.99 per month (or $139 per year). New members can start with a 30-day free trial! Join now and start shopping early Prime Day deals right away.