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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!
Womens Knee High Boots
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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
Shop: Amazon | Zappos | Lifestride
LifeStride X-Anita Black Leather Knee High Boots
Classy and elegant, readers Finding knee high boots that accommodate a range of calf widths can be tricky, but the Anita knee high black leather boots from Lifestride are designed with a flexible knit panel for the perfect fit. They’re also equipped with a foam insole, arch support, and a sturdy outsole that can tackle any terrain.
They’re a fabulous budget option, too! One wearer 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 a great price too.”
Shop: Amazon | Zappos | Franco Sarto
Frranco Sarto Meyer Flat Knee High Boots Wide Calf
If you’re looking for something streamlined, the Franco Sarto Meyer womens long black boots are a gorgeous choice! They’re made from luxurious synthetic leather that looks real and wears in nicely over time. Users say these fit wide calves, and they also come in a wide width option!
One wearer says, “The back zipper is a game changer. I travel a lot and putting on and taking off these boots is easier than any other pair I’ve owned. They are versatile, classic and comfortable. And very high quality!”
Shop: Amazon | Nordstrom | Zappos
Sam Edelman Penny Classic Knee High Boots
This classic pair of Sam Edelman long brown flat boots has that sophisticated, equestrian vibe that will easily elevate some slim-fitting jeans or even leggings! Add a pretty cashmere sweater and you have the perfect go-to outfit to wear all winter!
The leather is soft and luxurious, and wearers say they’re extremely comfortable, so they can definitely be your cold-weather sightseeing shoes. A reader raves, “Gorgeous, quality, and comfortable to walk in. I wore them all around Europe without breaking them in and had no pain whatsoever! Love them!!!”
Shop: Amazon | Nordstrom | Zappos
Blondo Tessa Black Knee High Boots with Heels
Blondo is a highly popular brand with TFG readers for practical yet cute travel boots, and these Blondo black leather high boots are a fabulous pair. They’re sleek and elevated yet easy to walk in, and the waterproof exterior will protect your feet from rain or slush.
A wearer says, “Comfortable and elegant! They’re dressier and pair well with skirts and dresses. They’re somewhat fitted around the calf and ankle but aren’t clingy at all.”
Teva Anaya Womens Brown Leather Boots Knee High
Sturdy, reliable, and cute, readers can confirm that these Teva Anaya brown boots won’t let you down in inclement weather! These black leather knee high boots wide calf option is ruggedly designed, so you can wear them stomping around the city or wandering around the countryside, and they’re easy to dress up for the evenings.
A happy wearer says, “They fit like a glove, the soles are textured which is a must have if you live or travel anywhere with ice. The heel is the perfect height for everyday wear. They are so comfortable!”
Aerosoles Binocular Womens Black Knee High Boots
These wedge knee high boots by Aerosoles are fully loaded for comfortable walking on your travels! They’re equipped with a flexible rubber sole that adds a bit of height and an insole that features foam padding and shock absorption. Function aside, they have a lovely, modern look.
This short and straightforward assessment speaks volumes, “Nice boots and perfect fit. I have wider calves, so the extra room was nice!”
Shop: Amazon | Zappos | Naturalizer
Naturalizer Jessie Leather Knee High Boots Wide Calf
So cute! The Jessie knee high riiding boots from Naturalizer are made from 100% leather and enhanced with buckle details that allow for some adjusting. Beyond the beautiful look, they feature ample cushioning and contoured support, with a flexible fit to keep you comfy throughout miles and miles of sightseeing.
A fan shares, “I love these so much. They’re SO cute and fit great on my calves. And the brown goes with more than I thought they would!”
Shop: Amazon | Nordstrom | Dansko
Dansko Celestine Knee High Boots with Arch Support
These Dansko knee high leather boots will add an instant touch of refinement to your look while also keeping your legs warm and dry. With a memory foam footbed and arch support, you’ll feel supported and energized wherever you go!
One wearer says, “Great arch support, soft leather, and super chic. Love them!.” Pair these boots with sweater dresses, jeans, or leggings.
Shop: Amazon | Nordstrom | Hunter
Hunter Black Rubber Knee High Rain Boots
If you’re heading somewhere rainy and potentially muddy, you may want to keep it simple and practical with these classic Hunter rain boots! This protective pair has excellent traction, so you’ll be sturdy and grounded wearing them. While they’re casual, they’ll look super cute with jeans and a sweater!
One wearer says, “Love them! They fit perfectly. I bought these for travel to Europe and they are very comfortable!”
Shop: Amazon | Zappos | Dr. Scholl’s
Dr. Scholl’s Brilliance Brown Leather Knee High Boots
These Dr. Scholl’s knee high boots are designed for wide feet and extra-wide calves, but they also come in regular sizes. Wearers rave about the memory foam cushioning and arch support that make these shoes suitable for long sightseeing adventures.
One review says, “These are comfy! I can wear them with long dresses and leggings all winter. There’s a nice buttery feel to the leather, the zipper is smooth, and the heel is just right for walking.”
Embrace the chill with a sweater dress and knee-high boots—comfort meets style.
How Do You Wear Knee High Boots
Wearing knee-high boots is an easy way to elevate your outfit, but how you wear them depends on the occasion, your personal style, and the look you’re going for.
Knee-high boots are a great match with slim-fitting pants like skinny jeans and leggings that’ll tuck seamlessly into the boots without bunching!
They can also add a sophisticated vibe to dresses and skirts, especially in cooler weather. Pair a knee-length or midi dress with some knee-high boots for an instantly chic look! If you want to stay cozy in the fall or winter look, add some tights or leggings. If you’re feeling bold, a mini skirt and knee-high boots create a fun, flirty contrast!
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 skirt and obviously aim for one that’s merino wool, or layer with thermals if you’re wearing something slightly lighter.
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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Hoping you’ll have another list later this year. All of the boots you listed are not available on the website in my size 🙁 Pretty boots though!
Hi Natalya, we are currently working on updating this post right now as things are selling out SO FAST. Will let you know once we’ve finished.
I love the boots YOU are wearing in this post (the ones with the leather panel over the top of the foot) but don’t see them among the recommendations. Would you please let us know what brand and style they are? Thank you!
Hi Gina,I got them at a New Years Day sale at Neiman Marcus in 2004 ☺️ They’re a Cole Haan and Nike collab. I still have them and wear them!