Support TFG by using the links in our articles to shop. We receive a small commission (at no extra cost to you) so we can continue to create helpful free content. As an Amazon Associate, we earn from qualifying purchases made on Amazon in addition to other retailers featured on the blog. Thank you, we appreciate your support!

 

While we rave about ankle booties here at TFG, womens tall boots can also be great for those times you want to cover your legs a bit more against the elements. Check out our top picks that are elegant yet uber comfy! 

 


Womens Knee High Boots


 

 

Table Of Contents

 

 

When it comes to fall and winter travel, ankle boots are definitely a winner when it comes to removing them at airport security without hassles and pairing them with a number of outfits, yet there’s still an enduring mystique to long boots, a topic that TFG readers have been asking about a lot recently!  

Boots that are knee highs not only help cover the legs fully in chilly weather; they also add a layer of sophistication to any travel outfit, whether the base is leggings, skinny jeans, or a wool skirt. And don’t forget those thermals or proper socks beneath your boots either!

 

 

most-comfortable-knee-high-boots-for-women

In a fave black knee high boots outfit while touring London

 

However, finding a knee-high boot that’s simple to wear and comfortable to walk in can be slightly challenging. The key is to choose a pair that has easy zipper access, some flexibility around the calf, cushioning in the footbed, and waterproof capabilities. But for any pair that you fall in love with that aren’t exactly waterproof, you can apply waterproofing spray to get them ready for inclement weather. 

 

Get ready to check out our picks for the top knee-high boots that are elegant, comfortable, and wearable anywhere!

 

 

Best Tall Boots for Women

 

 

most-comfortable-knee-high-boots-for-women

Shop: Amazon | Zappos | Selfridges

 

UGG Zarina Leather Knee High Boots

 

A reader fave, these UGG knee high leather boots are sleek, adding an instant touch of refinement to your look while also keeping your legs warm and dry, due to the wool-lyocell blend inside. They’re described as comfortable with a decently wide boot opening at 13” around.

A huge fan of these explains why UGG is so popular. “The style of this boot is perfect for where I live since we do have a lot of rain. They’re waterproof and warm.”

They further explain how to style them too! “I wear these boots with tights during the fall and winter months when I want to wear a skirt or dress. I also wear these boots with slacks, jeans, and leggings.”

 

If you love ankle boots too, check out our comparison review on between the UGG Simmens and the Teva De La Vina ankle boots right here!

 

 

teva-knee-high-boots-flat-heel

Shop: Amazon

 

Teva W De La Vina Flat Knee High Boots

 

Another reader fave, Teva makes comfy shoes as is, but these W De La Vina knee high shoes take the cake! The lining is comfy and the footbed is designed to walk on slippery surfaces; not to mention the great grip with the rubber sole and easy zip access when you need it.

One wearer loves these so much, she bought two pairs! “I bought one pair in black, the other pair in bison. The round toe gives my foot plenty of room, the deep tread on the rubber sole has lots of traction on slippery surfaces, and the lining is soft and comfortable. The heel is just high enough to give a little lift and low enough that I can wear these knee high suede boots all day. Love them!”

 

If you’re searching for wider knee high boots to accommodate a specific leg circumference, these boots are for you!

 

 

sam-edelman-knee-high-riding-boots

Shop: Amazon | Sam Edelman | Zappos

 

Sam Edelman Penny Classic Knee High Boots No Heel

 

We absolutely love this classic pair of Sam Edelman knee high boots! Paired with jeans and a cozy merino wool sweater, these boots will help curate the easiest winter getup.

The soft leather and snap detailing makes these uber stylish, we love the black color, but there are three other colors to choose from and there are regular and wide widths as well. Some users warn that the wide widths have quite the dearth so take that into consideration when choosing a size.

However, this reviewer is happy with the wider circumference and says. “I’ve been on a search for three years (not kidding) for the perfect leather wide calf boot, and thank god for these! They’re comfortable and amazing!”

 

Looking for ankle boot suggestions? Here are our top picks!

 

 

UGG-high-suede-boots

Shop: Amazon | Zappos

 

UGG Koolaburra Knee High Boots With Heel

 

The UGG Wilde boot is a through-and-through editor favorite and these UGGS knee high boots could be next, who knows! These gorgeous suede knee high boots have it all, soft upper, a neat buckle closure, a no-fuss side zipper, and the most important feature—Ortholite foam insoles for total comfort. 

Read what one user feels about these, “I love these knee high heel boots so much! I have them in black so wanted them in this color! They are sooo comfy, I can wear them for hours. The height is nice and you can wear them casually or dress them up!” 

Just note the height is 2”, but a sturdy stacked heel, so you can walk with some confidence as long as a slight heel works for you!

 

 

hush-puppies-knee-high-boots-without-heel

Shop: Amazon

 

Hush Puppies Women’s Knee High Boots

 

So classy and elegant, you can’t go wrong with this knee high boot from Hush Puppies. They are equipped with a sturdy rubber sole for sidewalks, a high-quality leather upper, and available in brown and black.

But what do wearers say about them? One says, “If you have a wide calf like me, these are the boots for you. I struggle to find boots to fit me, hence I look for ones with an elastic back and these are just perfect. They’re comfortable and are at a great price too.”

 

 

clarks-thick-heel-knee-high-boots

Shop: Amazon

 

Clarks Marana Trudy Women Knee High Leather Boots

 

A wonderful classic for travel or daily life is these Clark knee high boots. Full-grain leather, rubber sole, and an Ortholite footbed will have you walking anywhere and everywhere.

The styling is simple but a great staple time and again. A reviewer lays out all the pluses of this womens knee boot saying, “The calves fit athletic legs! There is a soft, springy footbed, and the Insoles can be removed to accommodate orthotics or other insoles. Finally, the leather feels durable and so far cleans up nicely.”

 

See more in our post about the best women’s leather boots!

 

 

sorel-knee-high-boots-no-heels

Shop on Nordstrom: Dark Brown | Black Version

 

Easy Spirit Women Knee High Boots

 

The Easy Spirit flat leather knee high boots are durable, stylish, and though not waterproof, are water-resistant. You could try a waterproofing spray to get extra protection.  This pretty shoe also has a removable cushioned insole that provides arch support.  

A review on these says, “I love these boots so much! I get so many compliments on them. They are so cute!” Note these come in the wide and medium sizes, so ensure you order the right ones for you. These also have a black version as well, available at this link!

 

 

eddie-bauer-gray-knee-high-boots

Shop: Amazon | Eddie Bauer | Moosejaw

 

Eddie Bauer Trace Knee High Woman Boot

 

A popular reader brand, the Eddie Bauer Trace boots are chic, yet practical. Waterproof leather, an elastic opening that measures about 15”, a removable EVA footbed allows you to use your own inserts or orthotics.  

This user adores her pair, saying, “These boots are great for spring, fall, and winter in the north! I bought them as a nicer/more stylish boot to wear in the winter besides snow boots, and they are just perfect. They’re warm, waterproof, and add a little style to any outfit. I was hesitant about the price and not knowing how I’d like them, but they were well worth every penny!”

I’m partial to the grey knee high boots option but there are three other classic colors to suit anyone’s style!

 

 

naturalizer-leather-knee-boot

Shop: Amazon | Nordstrom | Naturalizer | Zappos

 

Naturalizer Jessie Womens High Boots

 

These Naturalizer plus size knee high boots have diverse sizing, with a wide opening that measures 16” around, along with a cushioned insole for ample walking, and finally, a stylish look in the pretty buckle details. 

This die-hard boot searcher found what she wanted in these, saying, “I tried MANY pairs of boots to find the right ones, and these fit, especially along the calf. The footbed is very comfortable, as you would expect from this company. Overall, I’m quite happy so far.”

These Naturalizer knee high boots come in three wonderful colors: black, chocolate, and cinnamon.

 

Here are even more picks for stylish chic black knee-high boots

 

 

rockport-kneehigh-boots-for-women

Shop: Amazon | Nordstrom | Zappos

 

ARA “Paula” Weatherproof Tall Womens Boots

 

When it comes to quality knee highs shoes, these ARA “Paula” boots are totally unique! Not the standard leather, they are actually made of a waterproof Gore-tex and have a cushioned footbed and arch support. Plus, they come in half sizes, have a roomy opening of 14”, and  are stylish for something so practical! 

These high knee heel boots won’t let you down during wet or chilly weather, according to this user, “​​Fantastic boot. Comfortable, waterproof, attractive. I travel a lot and wear these exclusively. It’s a very nice change from leather. The Gore-tex is breathable, doesn’t scratch or mar as easily as leather, and keeps my feet warm and dry from one city to the next. Highly recommend them!”

 

 

most-comfortable-knee-high-boots-for-women

Shop: Amazon

 

Aerosoles Binocular Knee High Dressy Boots

Gorgeous and classy, this Aerosoles suede knee boot style has a flexible, rubber sole, a memory foam footbed, and extra give in the calf area with a boot opening of 16”, perfect for ladies with wider calves, so your legs and feet will feel comfortable and insulated. 

A reviewer gives her POV on their durability and comfort, saying, “I can’t believe how comfortable these boots are without even needing to break them in, and they’re very stylish! I’ve gotten many compliments. Not sure why some customers have said they’re too wide in the calf… I have slightly larger calves and had to unzip the extra extender, and they’re perfect that way. Without the extender, they would be too tight.

 

A super popular brand, the Aerosoles Conchlusion Gladiator sandals are also beloved by readers, so read our review on these too!

 

 

Timberland-high-leather-boots

Shop:Timberland | Zappos | Amazon

 

Timberland Knee High Boots – Graceyn

 

Talk about gorgeous, these Timberland below the knee boots are soft leather, with a sturdy rubber sole, and an Ortholite footbed that won’t quit on your feet. They’re waterproof too, so will keep your feet dry but don’t forget warm socks to keep them toast too! 

Do note that some users say these fit a bit narrow, so if you’re looking for a wide boot, this may not be it. Despite some of these considerations, this knee high boots style is highly popular and one review says they’re worth it and fit super well. “I wear these boots every day and the fit worked for me. They are comfortable to walk in and are very pretty boots. I highly recommend these boots!”

 

Here’s a collection of the best waterproof boots for travel!

 

 

Timberland-high-leather-boots

Shop:Timberland | Amazon

 

Timberland 14” Lace Knee High Boot 

 

Why not go for something super fun, like these Timberland lace knee high boots, but guess what? These actually pull on/off pretty easily. Made of full-grain leather with a round toe (so no pinching), the opening is slightly smaller, around 14”, but wearers still describe these as “very comfortable,” and the “colors are perfect.”

These are fully waterproof so they can handle the rigors of inclement weather and the lace-up detail adds tons of interest. One review says simply, “This is by far a superior boot and waterproof. The look, fit, and comfort are superb. These boots cost but ‘you get what you pay for’ rings true. I would recommend this product.

 

 

steve-madden-women-flat-knee-high-boots

Shop: Amazon | Steve Madden

 

Steve Madden Knee High Boots 

 

Elegant and classic, these Steve Madden knee high flat boots have a boot opening of 16”, smooth leather, and a sturdy sole.

Take these for a spin on a trip or locally and they’ll pair with anything from a dress to slacks. A reviewer says, “LOVE THEM! They fit perfectly according to size. I get a lot of compliments on them and they’re very comfortable.”

 

 

 

High Boots for Women Product Comparison Chart

 

BRAND | MODEL FEATURES | REVIEWS RATING | PRICE
UGG Zarina Leather Knee High Boots “I wear these boots with tights during the fall and winter months when I want to wear a skirt or dress. I also wear these boots with slacks, jeans, and leggings.” Check Price
Teva W DE LA Vina Dos Tall Boot “I bought one pair in black, the other pair in bison. The round toe gives my foot plenty of room, the deep tread on the rubber sole has lots of traction on slippery surfaces, and the lining is soft and comfortable. The heel is just high enough to give a little lift and low enough that I can wear these knee high suede boots all day. Love them!” Check Price
Sam Edelman Penny Classic Equestrian Boot Leather “I’ve been on a search for three years (not kidding) for the perfect leather wide calf boot, and thank god for these! They’re comfortable and amazing!” Check Price
UGG Koolaburra Knee High Boots With Heel “I love these knee high heel boots so much! I have them in black so wanted them in this color! They are sooo comfy, I can wear them for hours. The height is nice and you can wear them casually or dress them up!”  Check Price
Hush Puppies Women's Knee High Boots “If you have a wide calf like me, these are the boots for you. I struggle to find boots to fit me, hence I look for ones with an elastic back and these are just perfect. They’re comfortable and are at a great price too.” Check Price
Clarks Marana Trudy Women Knee High Leather Boots “The calves fit athletic legs! There is a soft, springy footbed, and the Insoles can be removed to accommodate orthotics or other insoles. Finally, the leather feels durable and so far cleans up nicely.” Check Price
Easy Spirit Women Knee High Boots “I love these boots so much! I get so many compliments on them. They are so cute!” Check Price
Eddie Bauer Trace Knee High Woman Boot “These boots are great for spring, fall, and winter in the north! I bought them as a nicer/more stylish boot to wear in the winter besides snow boots, and they are just perfect. They're warm, waterproof, and add a little style to any outfit. I was hesitant about the price and not knowing how I'd like them, but they were well worth every penny!” Check Price
Naturalizer Jessie Womens High Boots “I tried MANY pairs of boots to find the right ones, and these fit, especially along the calf. The footbed is very comfortable, as you would expect from this company. Overall, I’m quite happy so far.” Check Price
ARA “Paula” Weatherproof Tall Womens Boots “​​Fantastic boot. Comfortable, waterproof, attractive. I travel a lot and wear these exclusively. It's a very nice change from leather. The Gore-tex is breathable, doesn't scratch or mar as easily as leather, and keeps my feet warm and dry from one city to the next. Highly recommend them!” Check Price
Aerosoles Binocular Knee High Dressy Boots “I can't believe how comfortable these boots are without even needing to break them in, and they're very stylish! I've gotten many compliments. Not sure why some customers have said they're too wide in the calf... I have slightly larger calves and had to unzip the extra extender, and they're perfect that way. Without the extender, they would be too tight.” Check Price
Timberland Knee High Boots - Graceyn “I wear these boots every day and the fit worked for me. They are comfortable to walk in and are very pretty boots. I highly recommend these boots!” Check Price
Timberland 14” Lace Knee High Boot  “This is by far a superior boot and waterproof. The look, fit, and comfort are superb. These boots cost but 'you get what you pay for' rings true. I would recommend this product.” Check Price
Steve Madden Knee High Boots  “LOVE THEM! They fit perfectly according to size. I get a lot of compliments on them and they’re very comfortable.” Check Price

 

 

most-comfortable-knee-high-boots-for-women

 

How to Wear Knee High Boots

 

The beauty of these kinds of shoes is it’s easy to create a knee high boots outfit for tons of occasions during the chilly months. You can truly dress them up or down and always look put together. 

Usually, my knee high boots outfits consist of dresses that I can layer with tights, leggings, or skinny jeans. Here are a few styling ideas:

 

Best dresses to wear with knee high boots:

 

Best pants or leggings to wear with long knee boots:

 

When it comes to the topic of how to wear knee high boots with jeans, usually skinny jeans are best for tucking in into the boot or you can also go for boot cut jeans that can go over your boots. Both looks are awesome! 

An honorable mention is the Zella Live In leggings which I layer with some thermals underneath. You could also pair long flat boots with a skirt and obviously aim for one that’s merino wool, or layer with thermals if you’re wearing something slightly lighter. 

 

 

Knee High Socks With Boots

 

You can’t forget those! Here are some socks that can work well with boots knee high styles:

 

 

most-comfortable-knee-high-boots-for-women

Shop: Amazon

 

FoxRiver Her Thermal Boot Knee-High Socks

 

These long FoxRiver socks have a nearly 5-star rating on Amazon and come equipped with a WikiDry technology that keeps moisture away from your skin so you don’t have friction and cause blisters in your boots.

Along with the reinforced heel and toe, and specific panels for breathability, these are described by wearers as the “next best thing to a miracle cure for cold feet!”

 

 

most-comfortable-knee-high-boots-for-women

Shop: Amazon

 

JAVIE Merino Wool Graduated Compression Socks

 

Perfect for long walking bouts in your long leather boots, these JAVIE socks are 76% merino wool and much more breathable than other kinds of fibers. They also have compression so can help ease aching legs or swelling feet, both of which I can suffer from after walking for a long time!

A review sums these up well. “These socks are super comfortable. Just the right height and given the flat knit in the foot; they don’t take up extra volume in my shoes.”

 

 

most-comfortable-knee-high-boots-for-women

Shop: Amazon | Zappos

 

Darn Tough Solid Basic Knee High Lightweight Sock

 

A wildly popular brand, these Darn Tough socks are lightweight and are seamless, so they feel smooth and basically invisible. As usual, the merino wool blend is designed to wick away moisture but not the warmth. 

 

This brand is also great for hiking as well—check out our post on those specialty socks! 

 

 

Shorter Socks

 

Often you’re likely layering socks underneath pants or leggings and may not need long socks. These quick choices might help!

 

 

most-comfortable-knee-high-boots-for-women

Shop: Amazon

 

Kirkland Signature Trail Socks

 

Several readers agree that Kirkland’s merino wool socks are a top-notch. They come in a pack of four and you can choose from several different patterns and colors. With a cushioned footbed and reinforced heel and toe, these socks won’t let you down!

 

 

most-comfortable-knee-high-boots-for-women

Shop: Amazon | Moosejaw

 

Icebreaker Merino Lifestyle Light Crew Socks

 

Icebreakers come with a lifetime guarantee. Made from a mix of merino wool, nylon, and lycra, the fabric offers odor resistance. They’re some of the warmest socks and also have a  reinforced heel and Achilles support to keep your feet comfortable. 

 

To grab more ideas for socks, check out our post on the warmest socks for winter!

 

 


What do you think are the cutest knee high boots for fall and winter? Share in the comments!


 

For more fall and winter boots, please read:

 


 

LIKE THIS POST? PIN THIS PIC TO SAVE IT!

most-comfortable-knee-high-boots-for-women

 


We hope you liked this post on the most comfortable women’s high boots. Please share with your friends on Facebook, Twitter, and Pinterest. Thanks for reading!