The Best Over the Knee Boots to Wear All Winter Long (2023)

For a smooth and versatile over the knee boot, check out this stunning pair from Chinese Laundry. 

Featuring a breathable textile lining, round toe, and stylish wrapped block heel, these OTK boots go perfectly with any outfit from the casual to the formal! 

I’m continually surprised by Walmart’s fashion selections. 

Case in point: these burgundy brown over the knee boots. They’re simple, sleek and super affordable. I love the chunky block heel which makes them easy to walk in, and how pretty the shade of brown is in person. 

They’re not real leather of course, but for the price you can’t complain!

Normally, a big concern of mine with over the knee boots is naturally comfort. 

Fortunately, these boots from Stuart Weitzman have me covered (literally).

With a comfortable stretch suede fabric, a durable rubber outsole, and convenient tie strings at the top of the shaft, these boots are about as comfortable as they come!  

Naturally, petite women have every incentive to show off their flattering figures. 

(Those lucky little minxes!). 

If you are one such lucky lady, check out these OTK boots from Charles by Charles David, which offer a slim fit around the legs to go along with a cute stiletto heel!  

Skinny jeans. Skinny legs. Skinny, skinny, skinny. 

Ugh, what a life. 

Ladies with thin legs will love – and be able to fit in – these OTK boots from Steve Madden, which feature a relatively stiff (but fashionable) leather upper! 

Although I normally associate Kenneth Cole with men’s clothing, I have to admit how impressed I am with these OTK boots. 

Offering a soft suede upper, comfortable side zip closure, a round toe, and padded footbed, these boots are the perfect blend of chic and comfort! 

Let’s be honest. 

As fashionable as over the knee boots are, no one is exactly wearing them in perfect weather conditions. 

Waterproofing is never a bad idea, so thankfully these Blondo OTK boots are already shipped with a durable waterproof leather and a completely seam-sealed construction! 

While most OTK boots are built with a more muted leather or suede, these Cole Haan boots come with a nice, shiny polished leather. 

Throw in the round toe and trendy stacked heel, and these boots offer great value for a classy look!