17 Best Over the Knee Tall Boots for $100+

17 Best Over the Knee Tall Boots for $100+ by popular San Francisco fashion blog, Sylvie in the Sky: image of a woman outside wearing over the knee tall boots.

The best over the knee tall boots for Fall and Winter are those we can wear with almost everything to almost anywhere, make us feel like a million bucks (aka figure flattering), stand out in the best way, and pass the comfort test. Over the Knee (Tall) Boots have earned their rightful spot as an essential boot for every closet, and now there are not only every color, pattern, and material imaginable, the heel height diversity – most notably the flat and low heel options – and wallet friendly prices are the best yet. This Fall and Winter my Over the Knee Boots are on repeat for work, dinners, and weekends, and I’ve rounded up the 17 best over the knee tall boots at $100+ (some even lower!) that are on my wish list this season.

17 Best Over the Knee Tall Boots for $100+ by popular San Francisco fashion blog, Sylvie in the Sky: image of a woman outside wearing over the knee tall boots.

17 Best Over the Knee Tall Boots $100+

Over the Knee Tall Boot No.1: The Everyday Low Heel Black Boot

If there is only one boot to buy this season, it would be a low heel over the knee tall boot in black leather or suede. A low heel means it’s comfortable enough for everyday use, and a classic black goes with basically any outfit, for work, celebrations, and weekends. My everyday over the knee tall boots are black with a 1/2″ block heel and they’re the comfiest all day long!

Over the Knee Tall Boot No.2: The Whiskey Suede Boho Boot

Neutral boots in general are the most versatile way to go, but there’s a ranking of the coolest neutral shades and this season rich, whiskey brown is at the top. This warm brown suede boot works for weekends, work, all black, printed dresses, denim, and more.

Over the Knee Tall Boot No.3: The Classic Flat Black Boot

Everyone deserves a statement flat boot. It uplevels our most basic look and we can walk in them all day! My favorite flat boot is the #1 boot every winter, and a quality leather and simple design gives this boot years of life.

Over the Knee Tall Boot No.4: The Faux Snakeskin Boot

Snakeskin and it’s faux version have been a top accessory and footwear trend for the past few years, and continues to be a must have boot this season. Last year I lived in my short faux snakeskin boots, and added a fierce over the knee tall faux snakeskin boot to the mix this year. Over denim, with skirts and dresses, casual and dressed up – this tall snakeskin boot is the only accessory your outfit needs.

Over the Knee Tall Boot No.5: The Block Heel Neutral Boot

The pale gray/taupe neutral is a beautiful boot color, especially in suede. I’ve had this colored tall boot for 6 years and wear it all through boot season. Add a sturdy block heel to this over the knee boot and it’s comfy and chic.

Over the Knee Tall Boot No.6: The Lug Sole Black Boot

Lug sole boots are a longtime boot favorite for its durability, exceptional comfort (the rubber lug sole is far more forgiving on our bodies versus a wood heel), and cool, street style.

Over the Knee Tall Boot No.7: The Textured Faux Crocodile Boot

This textured crocodile pattern is another timeless style statement, in both footwear and accessories. This over the knee tall faux crocodile boot is all kinds of stunning, and is a more understated animal patterned boot option.

17 Best Over the Knee Tall Boots for $100+ by popular San Francisco fashion blog, Sylvie in the Sky: image of a woman outside wearing over the knee tall boots.

Over the Knee Tall Boot No.8: The Cool Camel Leather Boot

A camel leather over the knee tall boot is a cool and timeless boot for any time and place.

Over the Knee Tall Boot No.9: The Iconic Leopard Boot

The always cool leopard print never looked better in an over the knee tall boot. Just like her snakeskin and crocodile friends, this leopard print boot is the ultimate statement accessory.

Over the Knee Tall Boot No.10: The Statement White Boot

White boots continue to be one of the coolest footwear trends, and the over the knee tall boot options this year are even better than ever. I love this white suede version with denim, over black anything, and other winter patterns and cozy pieces.

Over the Knee Tall Boot No.11: The Olive Green Slouchy Boot

You know about me and my love for olive green coats – so no surprise my color crush extends to footwear too. My olive slouchy over the knee tall boot has been in rotation for 10+ years, and it’s finally time for me to replace my current boots for a new pair. This boot is the one on my wishlist and I can’t wait to get them for all my everyday and extra special outfits this season.

Over the Knee Tall Boot No.12: The Leather Buckle Boot

Buckle up! This moto inspired boot with cool buckle strap details takes this over the knee tall boot from ordinary to extraordinary.

Over the Knee Tall Boot No.12: The Dark Leopard Print Boot

The moodier version of the one and only leopard print is just as statement worthy and a fresh take on the classic animal print.

17 Best Over the Knee Tall Boots for $100+ by popular San Francisco fashion blog, Sylvie in the Sky: image of a woman inside wearing over the knee tall boots.

Over the Knee Tall Boot No.13: The Western Black Boot

Western inspired boots continue to reign supreme this season, and my western style black over the knee tall boots are one of my most worn boots this winter with dresses (see the red leopard dress photo below!), denim, and all things plaid and cozy.

Over the Knee Tall Boot No.14: The Studded Black Boot

Extra details like these head turning studs on this over the knee tall boot make it an It Boot that’s easy to wear but stand out in the best way.

Over the Knee Tall Boot No.15: The Taupe Tassel Tie Boot

Cool taupe shades are chic winter neutrals in boots and accessories, and this block heeled over the knee tall boot with the cinch tie and tassel details is a perfect shoe for the season.

Over the Knee Tall Boot No.16: The Easy Flat Black Suede Boot

Because we can never have too many flat black boot options! This easy, timeless over the knee tall black suede boot is cute and comfortable and can be worn with basically everything during the autumn and winter months.

17 Best Over the Knee Tall Boots for $100+ by popular San Francisco fashion blog, Sylvie in the Sky: image of a woman outside wearing over the knee tall boots.

Over the Knee Tall Boot No.17: The Comfiest Brown Suede Flat Boot

A gorgeous rich whiskey brown suede boot, this time in a flat over the knee tall boot version. Love this color and style for Autumn, Winter, and Spring outfits and occasions.

Now it’s your turn friends! What do you think it the best over the knee tall boots you’ll be wearing this season? Tell us in the comments, and shop all the best over the knee tall boots below!

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