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 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 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.

Dublin Ladies Kalmar SD Tall Boots {Buy Here}


Eric Michael Aurora {Buy Here}

Sofft Sharnell II Waterproof {Buy Here}

Major Shearling-Lined Waterproof Suede Boots {Buy Here}

Clarks Camzin Branch {Buy Here}


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!

Rocket Dog Sayla Vintage Worn Western Boot {Buy Here}

Clarks Camzin Strap {Buy Here}

comfortable booties

Comfortiva Chrysta Waterproof {Buy Here}

Naturalizer Tex Bootie {Buy Here}

Rocket Dog Fashionable Western Boots {Buy Here}

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! 

Walking Cradles Kimber {Buy Here}

Born Cove {Buy Here}

Women’s Lolla™ II Cut Out Bootie {Buy Here}

Born Brenta {Buy Here}

Born Brenta Bootie

Teva Anaya Bootie {Buy Here}

Teva Anaya Bootie for Fall


Born Syd {Buy Here}

Blondo Destin Waterproof Bootie {Buy Here}

Cute Travel Bootie

Born Kerri Bootie {Buy Here}

20 Cute & Comfortable Travel Boots for Women Walking the World

Clarks Clarkdale Arlo {Buy Here}

Hiking (& 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.

Danner Mountain Light Cascade Hiking Boot {Buy Here}

Sofft Baxter Waterproof {Buy Here}Green Comfortable boot

SOREL Emelie™ Conquest {Buy Here}

Kodiak Surrey II Waterproof {Buy Here}

Kodiak Surrey II

Taos Footwear Crave {Buy Here}

. . 

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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