20 Cute & Comfortable Travel Boots for Women Walking the World

Footwear—they’re the bane of every traveler’s packing list. Or is that just me? No matter how many times I pack my suitcase, I always pause when it comes to the shoes. Should I bring sneakers for active days and heavy, clunky boots for hiking? What about traveling to cities in the fall or winter—do I need a third pair of cuter, trendier boots for all of those afternoons of museum hopping? What are the best shoes for lots of walking?

If you’ve ever packed for Europe or South America in the colder fall, spring and winter months, alternating between nights out in the city and daytime hikes, you probably feel my pain here. But, I’ve learned a valuable shoe lesson in my years of travel. Wherever you’re going—whether it’s Florence in the winter, Geneva in the spring, or Tokyo in the fall—a pair of cute and comfortable 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.

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 leg warmers for extra style and warmth.

Sofft Samantha Tall Riding Boot {Buy Here}


Women’s Overland Annie Leather Riding Boots {Buy Here}

Sofft Sharnell II Waterproof {Buy Here}

Major Shearling-Lined Waterproof Suede Boots {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}

Comfortiva Chrysta Waterproof {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 a tall boot 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}

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

UGG Women’s Aureo Ankle Boot {Buy Here}

Hush Puppies Mazin Cayto Ankle Bootie {Buy Here}

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 hiking! 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 De La Vina Dos Alpine Boot {Buy Here}

SOREL Emelie™ Conquest {Buy Here}

Sofft Baxter Waterproof {Buy Here}Green Comfortable boot

Don’t think that just because you are traveling that you will have to sacrifice cuteness for comfort. You can absolutely have both! I’ve spent an embarrassing amount of time looking for the best pair of versatile 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? Leave your picks in the comments.

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