Every year without fail, my favorite part about the fall and winter seasons is the excuse to buy a new pair of knee-high boots (or two…or three). They’re the most classic cold-weather shoe staple, the perfect pairing to any outfit, from maxi dresses to mini skirts and tights to your favorite wide-leg jeans. But don’t just take my word for it—turn to celebrities and style icons Kendall Jenner and Gigi Hadid, who prove knee-high boots will always be in style.

I’ll never turn down an opportunity to buy some chic pointed-toe knee-highs or stylish yet practical riding boots, especially if they’re on sale. With Black Friday and Cyber Monday quickly approaching (aka the best time of the year to shop for amazing deals), now is the time to add some knee-high boots to your closet. After some meticulous searching, I found the best knee-high boots for every occasion, many of which are on sale now.

8 Best Knee-High Boots for Fall and Winter 2025:

Best Brown Knee-High Boots: EasyFox Pointed Toe Knee-High Boots, $69
Chic and Classic:Dolce Vita Auggie Boots, $250
Best Riding Knee-High Boots: SHIBEVER Knee-High Riding Boots, $37 (originally $56)
Fall and Winter Color Trend: COMJUY Burgundy Crocodile Knee-High Boots, $60
Best Suede Knee-High Boots: Steve Madden Lavan Boots, $143 (originally $169)
Dressy: Aldo Nathalee Knee-High Boot, $98 (originally $150)
Trendy Style: Dream Pairs Knee-High Motorcycle Riding Boots, $44 (originally $58)
Comfortable Block Heel: Franco Sarto Katherine Knee-High Boots, $85 (originally $195)

EasyFox Pointed Toe Knee-High Boots

I’ve been wearing brown nonstop this season, so finding these chocolate-brown pointed-toe knee-high boots on Amazon for under $70 felt like a major win. For starters, they have over 200 five-star ratings, with reviewers claiming they’re “so easy to wear, cute, and comfortable.” They also come in black, cream, burgundy, and a variety of other colors.

Dolce Vita Auggie Boots

I own these leather Dolce Vita Auggie Boots, and they’ve easily been my most-worn pair of shoes this fall. The heel is the perfect height IMO, giving me a bit of height without being difficult to walk in. And, they keep my feet happy and comfortable all day. I love the black for its versatility, but the suede brown is also gorgeous.

SHIBEVER Knee-High Riding Boots

Kendall Jenner makes riding boots look ultra-chic, so I, of course, had to find a similar pair on Amazon to recreate her look. This pair is on sale for under $50 and comes in black, chocolate brown, and light brown. Kudos to the silver buckles for making them look a tad more elevated, too.

COMJUY Burgundy Crocodile Knee-High Boots

Burgundy is one of the biggest fall color trends—plus, Gigi Hadid has proven that crocodile boots are here to stay. This marriage of color and texture led me to find these burgundy crocodile knee-high boots, on sale for less than $60. The gold buckle hardware adds a striking finishing touch, making them look much more expensive than they are.

Steve Madden Lavan Boots

Suede knee-high boots are one of my favorite ways to add a cozy-meets-dressy element to a fall outfit. This pair from Steve Madden in this creamy oatmeal shade makes for the perfect neutral shoe, and with a kitten heel and pointed toe, they’re a great everyday boot.

Aldo Nathalee Knee-High Boot

Looking for a taller heel? This pair from Aldo is stunning. Even better: The heel has some width and thickness to it, making it feel more sturdy. It’s available in black and camel brown, and is 35% off on Amazon.

Dream Pairs Knee-High Motorcycle Riding Boots

I love shoes that make a statement, which is why I’ve had my eyes on these Dream Pairs motorcycle riding boots. I think the black/brown color option is so unique and makes them even more visually interesting, while also making it easy to pair with a wide variety of outfits. The buckles all the way up the boot are my absolute favorite part.

Franco Sarto Katherine Knee-High Boots

If you prefer a chunky block heel, look no further than this pair of knee-highs from Franco Sarto. They’re made of stretch faux leather, making them ultra comfortable and easy to slip on and off. Plus, they have dozens of five-star ratings, with one reviewer saying she likes these boots for when she wants “to look nice for a night out but don’t want to worry about tripping/blisters.” Also important to note: They have wide sizing available.