20 Trendy Travel Boots for the Fall for Under $100

Shoes—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 trainers for active days and heavy, clunky boots for hiking? What about traveling to cities in the fall or winter—do I need a second pair of cuter, trendier boots for all of those afternoons of museum hopping?

If you’ve ever packed for Europe or South America in the colder months, alternating between nights out in the city and daytime hikes, you probably feel my pain here.

But, I’ve learned a valuable 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 comfy, trendy travel boots are a must-have, in my book. Your feet will thank you after your third consecutive day of non-stop sightseeing, and you (hopefully) won’t stand out as another tourist walking around in your white sneakers.

Cute & Trendy Travel Boots for the Fall for Under $100 | shoes, booties, comfy, comfortable, ankle, combat, rain

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.

I’ve found that when it comes to boots, you don’t always have to choose between walking pretty and having blister-free feet at the end of the day. Sure, it’s a challenge to find a good pair of walking boots that can double as trendy footwear for a night on the town, but it can be done!

I’ve spent an almost embarrassing amount of time looking for the perfect pair of versatile travel boots over the last year or so, and I’ve consolidated all of my top finds into this post. Hopefully, this trendy travel boot list will save you hours of painstakingly sorting through page after page of online shopping search results for “comfy practical stylish boot” and you’ll find something here that suits your needs—or at least sparks some boot-inspiration.


Hush Puppies Mazin Cayto Ankle Bootie

Trendy Travel Boots for the Fall

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Earth Summit Women’s Boot

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Annette White in Point Reyes California


Tretorn Lina Boot

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Teva Women’s Delavina Boot

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Fringe Ankle Bootie

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Sam Edelman Tinsley Rain Boot

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Modcloth Casual Influence Boot in Cognac

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Sole Society Natasha

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Annette White Walking in Montana


Dansko ‘Rosa’ Chelsea Rain Boot

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Roxy Bancroft Boots

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JBU Parker Boot

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Rocket Dog Thunder

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Hush Puppies Women’s Dorris Fairley Ankle Boot

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Clarks Faralyn May Waterproof Knee High Boot

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Annette White walking through Tokyo's Piss Alley


Naturalizer Jennings Wide Calf Tall Boot

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Western Distressed Cowboy Bootie

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Circus by Sam Edelman Women’s Kilbourn Fashion Boot

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Teva Women’s W Delavina Low-Mosaic Boot

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Dansko Women’s Lola Ankle Bootie

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Earth Origins Dolly Women’s Bootie

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2017-09-29T05:38:56+00:00 September 29th, 2017|Categories: BEAUTY & STYLE, LIFESTYLE|Tags: , |

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