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. We earn from qualifying purchases made to the featured retailers. Thank you, we appreciate your support!
While ankle booties are a timeless travel staple, knee-high boots offer the right combination of style, extra coverage and warmth, making them perfect for cold or rainy destinations. Check out our top picks for knee-high boots that will keep you warm, comfortable, and stylish—no matter where your travels take you!
Womens Knee High Boots
Table Of Contents
In a fave black knee high boots outfit while touring London
While finding knee-high boots that are easy to wear and comfortable to walk in can be a bit tricky, the key is to look for styles with zipper access, some flexibility around the calf, cushioning in the footbed, and waterproof features. And if you fall in love with a pair that isn’t waterproof, simply apply waterproofing spray to prepare them for any weather conditions.
Ready to discover the best knee-high boots that combine elegance, comfort, and travel-friendly practicality? Keep reading for our top picks!
Best Tall Boots for Women
Shop: Amazon | Zappos | Lifestride
LifeStride X-Anita Black Leather Knee High Boots
Classy and elegant, the Anita knee-high black leather boots from Lifestride offer the perfect blend of style and comfort.
Finding knee-high boots that fit a range of calf widths can be tricky, but these boots feature a flexible knit panel that ensures a customized fit. They also come with a foam insole, arch support, and a sturdy outsole, making them ready to tackle any terrain. What’s more, they’re a fantastic budget-friendly option.
One wearer shares, “If you have wide calves like me, these are the boots for you. I struggle to find boots that fit, so I look for ones with an elastic back, and these are just perfect. They’re comfortable and a great price, too!”
Shop: Amazon | Zappos | Franco Sarto
Franco Sarto Meyer Flat Knee High Boots Wide Calf
If you’re after a sleek, streamlined look, the Franco Sarto Meyer womens long black boots are a stunning choice. Made from luxurious synthetic leather that mimics the real thing, they soften and wear beautifully over time. Wearers share that these boots fit wide calves, and they even come in a wide width option!
One traveler shares, “The back zipper is a game changer. I travel frequently, and putting these boots on and off is easier than any other pair I’ve owned. They’re versatile, classic, comfortable, and incredibly high quality!”
Shop: Amazon | Nordstrom | Zappos
Sam Edelman Penny Classic Knee High Boots
These classic Sam Edelman long brown flat boots exude a sophisticated, equestrian vibe that effortlessly elevates slim-fitting jeans or leggings. Pair them with a chic sweater, and you’ve got the perfect winter outfit for sightseeing and travel!
Made from soft, luxurious leather, these boots are praised for their comfort, making them ideal for cold-weather exploration. One reader shares, “Gorgeous, high-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 favorite brand among TFG readers for their stylish yet practical travel boots, and these black leather high boots are no exception. Sleek and elevated, they’re also incredibly comfortable to walk in, with a waterproof exterior that keeps your feet dry in rain or slush.
One wearer shares, “Comfortable and elegant! They’re dressy and pair perfectly with skirts and dresses. They’re fitted around the calf and ankle but aren’t too tight or clingy.”
Teva Anaya Womens Brown Leather Boots Knee High
Sturdy, reliable, and stylish, these Teva Anaya brown boots are a favorite among readers for handling inclement weather with ease. Their leather knee-high design, available in a wide-calf option, is rugged enough for city exploring or countryside adventures, yet versatile enough to dress up for your evening plans.
One happy wearer shares, “They fit like a glove! The textured soles are a must-have if you live or travel anywhere with ice. The heel is the perfect height for everyday wear, and they’re incredibly comfortable!”
Aerosoles Binocular Womens Black Knee High Boots
These wedge knee high boots by Aerosoles are designed for maximum comfort during your travels. Featuring a flexible rubber sole that adds a bit of height, along with an insole that offers foam padding and shock absorption, they’re perfect for long days of walking. Beyond their functionality, they also boast a sleek, modern look.
One reviewer sums it up perfectly: “Nice boots and a perfect fit. I have wider calves, so the extra room was a great bonus!”
Shop: Amazon | Zappos | Naturalizer
Naturalizer Jessie Leather Knee High Boots Wide Calf
So cute! These Jessie knee high riding boots from Naturalizer are made from 100% leather and feature adjustable buckle details for a customized fit. Not only do they look beautiful, but they also offer ample cushioning, contoured support, and a flexible fit, making them perfect for miles of sightseeing.
One fan shares, “I love these so much! They’re SO cute and fit my calves perfectly. Plus, the brown color goes with way more outfits than I expected!”
Shop: Amazon | Nordstrom | Dansko
Dansko Celestine Knee High Boots with Arch Support
These Dansko knee high leather boots instantly elevate your look while keeping your legs warm and dry. With a memory foam footbed and built-in arch support, they provide comfort and energy for all-day wear.
One wearer shares, “Great arch support, soft leather, and super chic. Love them!” Perfect for pairing with sweater dresses, jeans, or leggings, these boots are as stylish as they are comfortable.
Shop: Amazon | Nordstrom | Hunter
Hunter Black Rubber Knee High Rain Boots
If you’re headed to a rainy or muddy destination, keep it simple and practical with these classic Hunter rain boots! With excellent traction, they’ll keep you sturdy and grounded, no matter the weather. While they’re casual, they look super cute paired with jeans and a sweater!
One wearer shares, “Love them! They fit perfectly. I bought these for travel to Europe, and they’re incredibly 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 to accommodate wide feet and extra-wide calves, but they also come in regular sizes too. Wearers rave about the memory foam cushioning and arch support, making them perfect for long days of sightseeing.
One review says, “These are so comfy! I can wear them with long dresses and leggings all winter. The leather has a lovely buttery feel, the zipper is smooth, and the heel is just the right height 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 effortless way to elevate your outfit, but how you style them depends on the occasion, your personal taste, and the look you’re aiming for.
When it comes to wearing knee-high boots with jeans, skinny jeans and leggings are typically the best option for tucking into the boots. Alternatively, bootcut jeans can be worn over the boots for a stylish, laid-back look. Both options are fantastic—it’s all about the vibe you’re going for!
They also add a sophisticated touch to dresses and skirts, especially in cooler weather. For an instantly chic look, try pairing knee-high boots with a knee-length or midi dress. To stay extra cozy in the fall or winter, layer with tights or leggings. And if you’re feeling bold, a mini skirt and knee-high boots create a fun, flirty contrast that’s perfect for a night out!
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
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
LIKE THIS POST? PIN THIS PIC TO SAVE IT!
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!
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!