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.
1.
Eric Michael Montana
Eric Michael $108.97
Give your everyday style a subtle western touch with the Eric Michael® Montana knee-high leather boots, designed with adjustable buckle straps for that classic riding-boot look.
2.
Sofft Taryn
Sofft $259.95
These Italian leather Taryn tall boots are crafted in sleek neutral waterproof finishes, giving you a chic, effortless way to move through drizzly days without slowing down your style.
3.
Sofft womens Sharnell Heel Waterproof
Sofft $239.95
This customizable waterproof suede boot gives you an effortlessly chic look with a side zipper for easy on-and-off, a comfy cushioned footbed, a 2-inch stacked heel, and an adjustable lace-up back so you can tailor the shaft height and fit to your perfect shape.
4.
Women’s Hudson Shearling-Lined Waterproof Suede and Leather Boots
Overland $299
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!
5.
The Annie
Tecovas $86.25
Meet The Annie, a best-selling tall cowgirl boot with a flattering 14-inch scalloped shaft, tonal stitching, and a fashion-forward snip toe—an elevated, timeless western style that only gets better with wear and pairs effortlessly with everything from denim to dresses.
6.
IUV Cowboy Boots For Women Western Cowgirl Boots
IUV $53.57
Handcrafted with intricate embroidery and a layered, textured design, these women’s cowboy boots blend authentic Western charm with modern style, making them a versatile, standout choice that effortlessly elevates everything from jeans to dresses.
7.
Spring Step L’Artiste Galop Boot for Womens
Spring Step L’Artiste
Hand-painted with floral embossing and crafted from naturally tanned leather, these ankle boots offer artful western charm, cushioned comfort, a smooth side-zip for easy on-and-off, and a wearable 2-inch heel that pairs effortlessly with everyday outfits.
8.
Rollda Women’s Cowboy Boots
Rollda $52.99
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!
9.
Heritage Lacer II Boot
Ariat $159.95
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.
10.
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.
11.
Sofft Bridgett
Sofft $169.95
Crafted from waterproof Italian suede with seam-sealed construction, this AQUASöfft boot keeps you stylish in wet weather with a wraparound strap detail, cushioned leather-lined footbed, inside zipper for easy wear, and a walkable stacked heel for everyday comfort and traction.
12.
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.
13.
Sofia Chelsea Boot – Women’s
Forsake $79.98
These casual Chelsea boots are built for an outdoor-ready lifestyle, featuring oiled leather and suede uppers, waterproof seam-sealed construction, a stable composite shank, cushioned PU and memory-foam footbeds, and grippy multi-surface traction for comfort and durability wherever you go.
14.
Comfortiva Rawnie
Comfortiva $139.95
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.
15.
Wexford H20 Boot – Women’s
Ariat $199.95
With a waterproof suede upper, a durable non-marking Duratread sole, and a lightweight ATS forked shank for support, these boots keep your feet dry and steady whether you’re out in the elements or on the move all day.
16.
Sofft Women’s Lonnie Black
Sofft $159.95
The perfect blend of style and adventure-ready comfort, this boot features a full-grain leather or Italian suede upper, cushioned leather-lined footbed with arch support, corduroy panel detailing, and a lightweight traction outsole—plus an inside zipper and heel tab for easy on-and-off and a low, everyday-friendly heel.
17.
SOREL Women’s Emelie III Chelsea Waterproof Boot
Sorel $119.99
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
18.
Crave
TAOS $250
Craving comfort and style? This urban boot delivers both with easy lacing and a side zipper, cozy faux-fur and leather lining, and a supportive Curves & Pods® footbed that keeps city adventures feeling effortless.
19.
Women’s Bree Wool-Lined Waterproof Suede Boots
Overland $279
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.
20.
Born Moraga
Born $136.00
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.
21.
Sorel Women’s Emelie II Lace Bootie
Sorel $95.99
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.
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.
22.
ANJOUFEMME Casual Winter Hiking Boots For Women
ANJOUFEMME $45.99
These women’s snow-hiking boots deliver rugged protection with anti-skid, wear-resistant, water-resistant performance—making them a reliable partner for trekking, camping, and everyday outdoor adventures.
23.
Sabrina 20
Rieker $145
Stay warm, comfortable, and ready for winter in the Rieker® Sabrina 20 boots, featuring a water-repellent finish, cozy lining, durable stitch-down construction, lace-and-zip entry for a secure fit, a removable cushioned insole, and grippy traction for cold, wet days.
24.
PATRIZIA Women’s JADELYN Hiker Booties
PATRIZIA $69.95
These cozy, city-meets-outdoors winter booties feature a sleek faux-leather design with a warm sweater-knit collar, inner zipper and laces for an easy, secure fit, durable weather-ready construction, and a comfortable lifted sole that keeps you stylish and supported from sidewalks to scenic trails.
25.
Women’s Out N About Wedge Bootie
Sorel $83.92
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?
Ready to Start living your bucket? Use my Favorite Resources:
Finding Ideas
Of course this bucket list blog and my bucket list are great resources, but you can also use my free printable 2,000 bucket list ideas.
Naming Your List
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Storing Your List
I’ve created the perfect Google Sheets Bucket List Tracker Spreadsheet, that helps you store your list, plus keep track of all those checkmarks you’ll be making on it!
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Hey guy, I have read this article thoroughly the category of hiking shoes attracts me a lot as I’m a big lover of hiking. I still remember it was a long time back when I used to go out with my aunt towards northern areas for hiking then I bought for her one of the best hiking shoes from the market. Anyhow the shoe category and design look stunning.
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