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 Florence, Geneva 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 Modern Boho’s lace trim knee highs) or trendy boot cuffs for extra style and warmth.
Eric Michael Marcella
Eric Michael $218.95
These cute 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.
Introducing the Sofft Bluma – your new go-to shoes for comfort and style! With their chic design and cushioned support, these versatile kicks will keep you walking on clouds all day long.
Sofft Sharnell II
Meet your new favorite fall companion – the Sofft Sharnell II! These boots are not only stylish and on-trend but also offer exceptional comfort, making them perfect for all your adventures.
Women’s Hudson Shearling-Lined Waterproof Suede and Leather Boots
Step into ultimate autumn in luxury with our Women’s Hudson Shearling-Lined Waterproof Suede and Leather boots!Stay fashion-forward and weather-ready with these cozy, waterproof companions that will keep your feet happy and warm during the coldest fall days.
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!
Whether you’re dressing up for a night out or heading out for a day on the ranch, 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.
Rocket Dog Women’s Sayla Vintage Worn PU Western Boot
Rocket Dog $24.50 – $54.67
These Rocket Dog Western boots are the perfect addition to your travel 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.
Guess Ginnifer Boot
Elevate your footwear game with the Guess Ginnifer Boot! These chic and versatile boots in a stunning color are the perfect addition to any outfit, adding a touch of style and confidence to your step.
Rollda Women’s Cowboy Boots
Whether you’re two-stepping on the dance floor or strolling through town, get ready to turn heads with the Rollda Western Cowboy Boots. Embrace your inner cowgirl in these stylish and comfortable boots that effortlessly combine classic Western design with modern flair.
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!
Heritage Lacer II Boot
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.
Ariat Wexford Waterproof Boots
Ariat $149.97 – $299.90
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.
Sofft Bellis III
Sofft Bellis III Boots are the perfect footwear for fall weather. The leather upper and the gathered details add a touch of style. The low heel provides just enough height to ensure hours of comfortable wear.
BORN Women’s Kerri Ankle Boot
Born $74.30 – $242.76
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 zip makes it easy to get on and off.
Clarks Clarkdale Arlo Women’s Boot
Clarks $34.51 – $214.95
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 of walking those cobbled streets!
Say hello to all-day comfort with the Comfortiva Rawnie. These sleek and supportive shoes are the perfect blend of style and cushioned bliss, making them your go-to choice for any travel occasion.
Get ready to “sole” in love with the Birkenstock Ebba Natural Leather boots. They have a chic city style and foot-hugging comfort for your exploring escapades. Embrace happy feet and walk your way to endless adventures in these must-have boots that take fashion and relaxation to a whole new level.
Step into shoe paradise with Born Griffin—your secret weapon to conquer the world with comfort and charm. These shoes combine fashion and functionality, ensuring you strut through your day with flair and grace.
Women’s Emelie III Chelsea Bootie
Step into the spotlight with the Women’s Emelie III Chelsea Bootie—the sassy sidekick your vacation wardrobe has been longing for.
Motorcycle/Combat Style Boots
TAOS Boot Camp
Taos Boot Camp = your new stylish companion for every adventure. With its rugged charm and versatile smoke rugged color, these boots are ready to take on any terrain while keeping your feet comfy and happy throughout the journey.
Women’s Bree Wool-Lined Waterproof Suede Boots
Meet your new travel and fashion essential—the Women’s Bree Wool-Lined Waterproof Suede Boots. With their cozy wool lining and waterproof suede, these boots keep your feet warm and dry while adding a touch of style to your outfits.
Say hello to shoe perfection with Born Moraga – the stylish sidekicks that will have your feet singing “Hallelujah!” With their trendy color and heavenly comfort, these shoes are ready to take you on a fabulous journey, one confident step at a time.
Sorel Women’s Emelie II Lace Bootie
Introducing the Women’s Emelie II Lace Bootie—your ultimate choice for style and comfort! Combining chic design with Sorel’s dependable quality, these boots strike the perfect balance between fashion-forward and practicality.
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.
Teva Midform Boot
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.
Kodiak Women’s Surrey II Waterproof Fashion Boot
Kodiak $54.28 – $174.95
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. It has a low heel and a round toe, and is finished with a lace-up closure for a secure fit.
UGG Hapsburg Ankle
Meet the UGG Hapsburg Ankle boots – your ultimate blend of style and coziness! With their chic color and signature UGG comfort, these boots are your perfect companions for staying warm and fashionable throughout any season.
Women’s Out N About Wedge Bootie
Get ready to step up your style game with the Women’s Out ‘N About Wedge Bootie—the perfect way to elevate your fashion while staying down-to-earth! These tennis shoe style booties boast a wedge design that adds a touch of sass to any outfit, while providing Sorel’s reliable quality,
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?
This post may contain affiliate links. If you make a purchase through my links, I earn a commission that helps to keep this blog running—at no extra cost to you. For more information read my full disclosure.
You Might Also Enjoy
25 Cute Winter Jackets: Best Coats for Women Travelers
20 Cute Travel Inspired Jewelry Accessories 15 Cute Winter Jackets Fit for Travel
Cute Luggage Tags: 25 of the Best Ones for Your Travel Bag