Footwear—they’re the bane of every women’s packing list. Or is that just me? No matter how many times I packed my suitcase, I always used to pause when it comes to the shoes, especially in the fall. Should I bring comfortable sneakers for active days and heavy, clunky hiking boots for outdoorsy bucket list adventures? What about traveling to cities in the fall—do I need a third pair of cuter, fashionable ballet flats for all of those afternoons of museum hopping? What are the best (and most comfortable) shoes for lots of walking in the brisk fall weather? The answer to all of the above is a pair of cute and comfortable travel boots. 

If you’ve ever packed for Europe or South America in the colder fall months you will understand that alternating between morning brunch, nights out in the city and daytime hikes can be a challenge for footwear. But, I’ve learned a valuable shoe lesson in my many years of travel. Wherever you’re going from September to December—whether it’s FlorenceGeneva or Tokyo—a pair of cute and comfortable women’s travel boots are a must-have.

Unfortunately, it seems incredibly difficult to come across the perfect balance of that ideal boot trifecta: comfort, style, and practicality. Difficult, yes—but not impossible.


The Best Fall Travel Boots for Walking Women (Fashionable, Cute & Comfortable!)


Tall Riding & Knee High Boots

A tall riding boot is my go-to shoe for almost any cold-weathered trips—fall thru spring! The height keeps my calves warm, which is particularly helpful when they’re paired with a skirt. Plus, if you find some flat boots with a little tread, they can be used for light hiking too. Don’t forget to add some cute boot socks (like these) or trendy boot cuffs for extra style and warmth.

Annette White in Bodega California wearing riding boots

1.

Aerosoles Star Combat Boots

Aerosoles $224.99

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These boots mean business. The combat design is super trendy and features a sturdy lace-up front with an easy side zipper.

2.

Women’s Cortina Valley Tall Boots

Timberland $220.00

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These boots are made for walking…and looking good, of course. The Timberland Women’s Cortina Valley Tall Boots combine style and function to create a boot that can be worn in many weather condition. 

3.

Eric Michael Marcella

Eric Michael $218.95

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These Michael Marcella boots will not only keep your feet warm, but they will keep them dry too! They are made with soft leather and suede uppers with a strap at the calf and zipper closure.

4.

Women’s Hudson Shearling-Lined Waterproof Suede and Leather Boots

Overland $299

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Overland’s Women’s Hudson Shearling-Lined Waterproof Suede and Leather boots are the perfect choice for stylish women who want to stay warm and dry all winter long. These beautiful boots are made from waterproof suede and leather, and they’re lined with cozy shearling to ensure that your feet will always be toasty-warm.

Western Inspired Footwear

Doesn’t everyone have a little cowboy in them? I certainly do. And all of the ones below are cool country footwear. The first western inspired boots (Rocket Dog) aren’t too flat, they have a little bit of a heel, so maybe wouldn’t be the best for the narrow cobbled streets of Spain, but despite the height they are incredibly comfortable. I brought them with me while traveling through India on the Palace on Wheels luxury train and wore them at every stop, even to the Taj Mahal!

Western booties in India

5.

The Josie

Tecovas $275

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The Josie boots from Tecovas are the perfect blend of fashion and function. Made from premium water-resistant suede, they’re designed to mold to your feet for a comfortable, custom fit. And, with their stylish stitching and harness detail, they’ll add a touch of western flair to any outfit. Whether you’re dressing up for a night out or heading out for a day on the ranch, The Josie boots are sure to become your go-to footwear.

6.

Rocket Dog Women’s Sayla Vintage Worn PU Western Boot

Rocket Dog $24.50 – $54.67

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These Rocket Dog Western boots are the perfect addition to your wardrobe. The stacked heel adds a touch of height without being too dramatic, and the pointed toe keeps them looking Feminine. Whether you’re pairing them with jeans and a tee or a dress and jacket, these boots will give you the confidence you need to take on anything. 

Ankle Boots & Booties

Ankle boots are super stylish these days and might be the perfect choice for a little bit warmer weather where tall travel boots may seem out of place. They are also great when traveling to Asian countries like Japan where it’s a part of Japanese culture and tradition to remove your shoes before entering many places. You want something easy to slip-on and off! 

7.

Women’s Courmayeur Valley Chelsea Boots

Timberland $99.99

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If you’re looking for a stylish and versatile ankle boot that pulls on easy, the Timberland Women’s Courmayeur Valley Chelsea Boot is a great option. It features a sleek design with a comfortable fit, making it ideal for everyday wear. The boot is made of high-quality materials, providing durability and long-lasting wear. 

8.

Heritage Lacer II Boot

Ariat $159.95

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The Ariat Heritage Lacer II Boot is a tough and durable boot that is built to last. The boot is made of 100% full-grain leather and features a Goodyear welt construction for durability and flexibility. 

9.

ABEO B.I.O.system Verity Neutral

Abeo $149

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The ABEO B.I.O.system Verity Neutral Boot is a comfortable, versatile boot that can be worn for both casual and dressy occasions. The upper is made of soft, supple leather that conforms to the foot, and the inside is lined with a smooth fabric that feels good against the skin. The boot has a rounded toe and a low heel, making it easy to walk in. The outsole is made of rubber, which provides good traction on slippery surfaces.

10.

Ariat Wexford Waterproof Boots

Ariat $149.97 – $299.90

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The Ariat Wexford Waterproof Boots are a great choice for anyone looking for a stylish and practical boot. The full-grain leather upper is both water-resistant and soft to the touch, while the durable rubber outsole provides excellent traction. The 200 grams of insulation keep your feet warm in cold weather, and the moisture-wicking lining helps to keep them dry. 

11.

Sofft Bellis III

Sofft $145.95

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Sofft Bellis III Boots are the perfect footwear for cooler weather. The leather upper is lined with a soft fabric that helps to keep your feet warm, and the gathered details add a touch of style. The low heel provides just enough height to ensure hours of comfortable wear, while the inside zip makes it easy to get the boots on and off. 

12.

Sofft Lilia

Sofft $175.95

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The Sofft Lilia Boots are a stylish and practical choice for any woman. With a versatile design that can be worn with jeans or skirts, these boots are perfect for any occasion. The uppers are made from soft suede, and the lining is made from breathable fabric to keep your feet comfortable all day long. The rubber outsole provides traction and durability, while the stacked heel adds a touch of style. 

13.

Born Malta Bootie

Born $119.99

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The Born Malta Bootie is a stylish and comfortable shoe that can be dressed up or down. The upper is made from soft, supple leather that molds to your foot for a custom fit, and the stacked heel provides gentle support and definition. The bootie also features an interior zip for easy on and off, as well as a rubber outsole for traction and durability. 

14.

BORN Women’s Kerri Ankle Boot

Born $74.30 – $242.76

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The BORN Women’s Kerri Ankle Boot is a stylish and practical choice for any woman’s wardrobe. The upper is made of soft, supple leather that conforms to the foot for a comfortable fit, and the inside zip makes it easy to get on and off. The rubber outsole provides traction and durability, while the stacked heel adds a touch of style. The boot also features an OrthoLite® insole for cushioning and support, and a breathable mesh lining for comfort. 

15.

Clarks Clarkdale Arlo Women’s Boot

Clarks $34.51 – $214.95

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Clarks has been making quality footwear for men and women for over 200 years, and the Clarkdale Arlo boot is a great example of their craftsmanship. These boots are made with a soft leather upper that conforms to your foot, and they have a durable rubber outsole that can withstand wear and tear. 

16.

Koolaburra by UGG Berea Ankle

UGG $99.95

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The Koolaburra by UGG Berea Ankle Boot is the perfect way to keep your feet warm and stylish all winter long. Made from water-resistant suede, it features a cozy sheepskin lining that will keep your feet toasty even in the coldest temperatures. The low profile design makes it easy to wear with jeans or leggings, and the Lugsole outsole provides traction and stability on icy surfaces. 

17.

Dear Bootie

White Mountain $79.00

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The White Mountain Dear Bootie has strong leather construction and thick rubber sole. This boot is built to withstand even the most challenging terrain. But the Dear Bootie isn’t just about function – it’s also fashion-forward, with a trendy cutout design that will make you stand out on the streets or a trail.

Motorcycle Style Boots

18.

Harness 8R

Frye $398.00

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The Frye Harness 8R Boot is a popular style of boot that is known for its durability and classic design. The upper part of the boot is made from a single piece of leather, which is then stitched to the sole. This construction makes the boot very durable and helps it retain its shape over time. The boots also feature a Goodyear welt, which is a type of stitching that further reinforces the boot and makes it resistant to water damage. 

19.

Softwalk Indiana

Softwalk $89.95

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The IndianaBoot by Softwalk is the perfect mix of style and comfort. The full-grain leather uppers provide support and durability, while the microfiber lining ensures a soft, comfortable fit. The boots also feature a contoured footbed with arch support, which helps to reduce foot fatigue which is super important when traveling!

20.

Aerosoles Arezzo

Aerosoles $170

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Looking for a stylish and comfortable boot to take you from fall to winter? Check out the Aerosoles Arezzo boot! This boot is made with a faux soft suede upper, and it features a cozy fur lining to keep your feet warm all season long. 

21.

Taos Combo

Taos $250.00

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The Taos Combo Boots are a stylish and versatile option for any wardrobe. The soft, supple leather upper is accented with a stitching detail that adds a touch of refinement. The side zip closure makes them easy to slip on and off, and the stacked heel provides just enough lift.

Hiking-Inspired Boots

I don’t know about you, but I think hiking boots are cute, so I wear them even when I am not on the trail! They can be paired with jeans, hiking pants or a pair of stylish leggings to fit many different occasions. Plus, most are super comfortable because they have a more rounded toe so you are not squishing your tootsies.

Annette standing on a rock at Awarmie Mountain

22.

Women’s Lennox Hiker Stkd Boot

Sorel $200.00

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The Sorel Women’s Lennox Hiker Stkd Boot is a stylish and practical boot that will keep your feet warm and dry all winter long. The boot is made of waterproof leather and features a rubber sole for traction in all kinds of weather. The boot also has a comfortable EVA footbed and a shock-absorbing heel for added comfort.

23.

Women’s Hi-Line Hiker Boot

Sorel $185.00

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Looking for a stylish and comfortable boot to take you from the city to the mountains? Check out the Sorel Women’s Hi-Line Hiker Boot. This boot is made with a waterproof leather and suede upper, so you can rest assured your feet will stay dry no matter what the weather throws your way. The removable EVA footbed provides cushioning and support, while the rubber sole gives you traction on any terrain. Plus, the cute laces and stitching add a touch of style. 

24.

Teva Midform Boot

Teva $140

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This boot is designed to provide both style and comfort, and it comes in a variety of colors and sizes. The boot has a mid-calf height, making it perfect for wearing with jeans or leggings. It also features a cushioned insole, making it comfortable to wear all day long. The outsole is made from durable rubber, making it ideal for walking on wet or icy surfaces. And the boot is easy to slip on and off, thanks to the side zipper closure. 

25.

Kodiak Women’s Surrey II Waterproof Fashion Boot

Kodiak $54.28 – $174.95

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The Kodiak Women’s Surrey II Waterproof Fashion Boot is a stylish and practical choice for wet weather. The boot is made from waterproof leather, with a seam-sealed construction to keep feet dry. The boot has a low heel and a round toe, and is finished with a lace-up closure for a secure fit. 

Don’t think that just because you are traveling that you will have to sacrifice cuteness for comfort or fashion for fit—you can absolutely have it all! I’ve spent an embarrassing amount of time looking for the best pair of versatile women’s travel boots, and these are my top finds. Hopefully, they give you some boot-inspiration for your next trip. What are your favorite travel boots that are made for walking?

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