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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!
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, comfy jeans, or a wool skirt. And don’t forget those thermals or proper socks beneath your boots either!
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
Teva Anaya Flat Knee High Boots With Slight Heel
A reader fave, Teva makes comfy shoes as is, but these Teva Anaya 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!
Dansko Celestine Leather Knee High Boots
These Dansko knee high leather boots are sleek, adding an instant touch of refinement to your look while also keeping your legs warm and dry.. With a natural arch technology that creates the best arch support available, enhanced with an EVA memory foam footbed so you will feel supported and enjoy a soft ride wherever you go.
Dansko shoes for women are chosen by those who expect modern style with complete comfort wherever the day takes them.
One wearer says, “Great arch support, soft and super chic. Love them!.” Wear these boots with slacks, jeans, and leggings.
Shop: Amazon | Sam Edelman | Nordstrom |Zappos | Macy’s
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!
Shop: Amazon
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!
Shop: Amazon | Zappos | Macy’s| Lifestride
Lifestride Women’s Knee High Boots
So classy and elegant, you can’t go wrong with this knee high boot from Lifestride Anita. They are equipped with a sturdy rubber sole for sidewalks, a high-quality leather upper, and available in 3 colors and wide sizes too.
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.”
Cole Haan Women Knee High Leather Boots
A wonderful classic for travel or daily life is these Cole Haan knee high boots. Soft leather, rubber sole, and a soft footbed will have you walking anywhere and everywhere.
The styling is simple but a great staple time and again. A reviewer says about this womens knee boot, “Beautiful boots great quality perfect fit. Great for wet days. So glad I bought them!”
See more in our post about thebest women’s leather boots!
Shop: Amazon
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.
When it comes to shoes, it’s vital for feet to feel comfortable at all times. Readers swear by shoe inserts to help boost support for long periods of walking!
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!
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 morepicks forstylish chic black knee-high boots!
Shop: Amazon
ARA “Sadie” Weatherproof Tall Womens Boots
When it comes to quality knee highs shoes, these ARA “Sadie” boots are totally unique! Made with waterproof PRO construction with an impermeable barrier and have a cushioned footbed and arch support. Plus, they come with ATS lightweight forked shank for enhanced support, 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, “Cute, warm, waterproof. Comfortable. Highly recommended”
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!
Shop: Amazon | Nordstrom | UGG
UGG Waterproof Rubber Knee High Boots
Talk about edgy and fun, these UGG below the knee boots are soft, with a sturdy rubber sole, and an EVA 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!
This knee high boots style is widely lauded by users who say these are awesome because they’re lightweight and breathable. Its upper is crafted from fleece, synthetic, textile, and neoprene and features a round toe silhouette. One wearer says, “Hands down a great boot for the bad weather. Feet are dry and cozy from the wind and rain.”
Here’s a collection of thebest waterproof bootsfor travel!
Shop: Amazon | Nordstrom|Franco Sarto
Franco Sarto Meyer Knee High Boots
If you’re looking for some cute fall knee high boots, the Franco Sarto Meyer is a stellar choice! With an artisan leather finish and a back zip, these would make great flight shoes. And users say these fit wide calves.
One says, “I love that the larger shaft actually gives my calves room! The boots are comfortable, well made and look great with a dress or leggings and a tunic. Years ago, I had to have riding boots custom made due to my generous calves.”
Shop: 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.”
While knee high boots and ankle booties are forever classics, our readers are loving these mid-calf boots!
Shop: Amazon
Pikolinos Knee High Boots
Elegant and classic, these Pikolinos knee high flat boots have a boot opening of 14”, 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, “Gorgeous boots! I am 5’2” and have so much trouble finding boots with shafts that are not too tall. These fit me perfectly. The front hits just below my knee and the back hits me about an inch below my knee. The color (brown) is very rich looking. The leather is extremely soft and so far they are very comfortable. However I have not worn them for any length of time yet.”
High Boots for Women Product Comparison Chart
| BRAND | MODEL | FEATURES | REVIEWS | RATING | PRICE |
|---|---|---|
| Teva Anaya Flat Knee High Boots With Slight Heel | 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 |
| Dansko Celestine Leather Knee High Boots | "Great arch support, soft and super chic. 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 |
| Lifestride 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 |
| Cole Haan Women Knee High Leather Boots | “Beautiful boots great quality perfect fit. Great for wet days. So glad I bought them!” | 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 “Sadie” Weatherproof Tall Womens Boots | "Cute, warm, waterproof. Comfortable. Highly recommended." | 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 |
| UGG Waterproof Rubber Knee High Boots | "Hands down a great boot for the bad weather. Feet are dry and cozy from the wind and rain." | Check Price |
| Franco Sarto Meyer Knee High Boots | “I love that the larger shaft actually gives my calves room! The boots are comfortable, well made and look great with a dress or leggings and a tunic. Years ago, I had to have riding boots custom made due to my generous calves.” | 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 |
| Pikolinos Knee High Boots | “Gorgeous boots! I am 5’2” and have so much trouble finding boots with shafts that are not too tall. These fit me perfectly. The front hits just below my knee and the back hits me about an inch below my knee. The color (brown) is very rich looking. The leather is extremely soft and so far they are very comfortable. However I have not worn them for any length of time yet.” | Check Price |
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:
- Cozy Winter Dresses
- Midi dresses
- LBD (little black dress)
- Dresses with pockets (would look fab with long boots)
Best pants or leggings to wear with long knee boots:
- Best Black Travel Pants
- Faux leather leggings (including one of my faves, the Spanx moto leggings)
- Jeans Travelers Love
- Ponte pants
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 skirtand 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:
Minus33 Merino Wool Ski and Snowboard Sock
Minus33 Quality Merino Wool Sock
Minus33 combines sustainable, 100% Merino wool with sleek design elements in all their clothing. This merino wool knee high socksare built to provide you with total support and comfort during your trips, no matter the weather. Blended with nylon to promote a comfortable, itch free experience.
These are unisex socks, and are super cozy with a cushioned footbed and reinforced heel and toe, these warm socks will last all season long.
Shop: WoolX
WoolX Thermal Boot Knee-High Socks
These long WoolX Extreme extra cushion over the calf socks is equipped with quick drying and moisture wicking fabric that keeps moisture away from your skin so you don’t have friction and cause blisters in your boots.
Along with the ultra smooth seamless toe, and specific panels for breathability, they are also have plush merino wool cushioning and antimicrobial that destroys odor. If you’re looking for a liner sock, here is another option.
Shop: Amazon
Sockwell Merino Wool Graduated Compression Socks
Perfect for long walking bouts in your long leather boots, these Sockwell socks are 32% merino wool, 32% nylon 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.”
Shop: Amazon
Darn Tough Due to North Knee High Lightweight Sock with Cushion
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!
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! Also available in 6pack here!
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.
Darn Tough Vermont 1/4 Cushion Socks
Darn Tough Merino Wool Socks
Darn Tough socksare just that — darn tough. They’re made from a mix of merino wool, nylon, and spandex for a comfortable fit. With high density terry loop padding, the sock won’t wear down even when you’re hiking nonstop.
One reader said they’re great due to their lifetime warranty, with another adding, “Darn Toughs are awesome,” and a third reader saying, “I’ll never even bother buying another brand of sock again. They’re made in Vermont and are designed for the winters there”. They also have solid basic crew light socks here!
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:
- The Best Flat Boots for Travel: Our Fall/ Winter Must-Haves!
- Must-Have Combat Boots
- Chelsea Boots: Our Latest Travel Shoe Obsession
- Gotta-Have Boots for Fall
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