20 Cute & Comfortable Travel Boots for Women Walking the World

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? 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, 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.

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 Cute & Comfortable Travel Boots for Women Walking the World


20 of the Best Cute & Comfortable Travel
Boots for Women Walking the World


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 best pair of versatile travel boots, and I’ve consolidated all of my top finds into this post. Hopefully, this list will save you hours of painstakingly sorting through page after page of online shopping search results for “comfy practical stylish boots” and you’ll find something here that suits your needs—or at least sparks some boot-inspiration.


Hush Puppies Mazin Cayto Ankle Bootie {Buy it Here}

Trendy Travel Boots for the Fall


Teva De La Vina Dos Alpine Boot {Buy it Here}

Cute & Comfortable Travel Boots for Women Walking the World


Earth Summit Women’s Boot {Buy it Here}

These fashionable shoes are inspired by hiking boots, but with a little added trendiness. They can be paired with jeans, hiking pants or a pair of cute leggings to fit many different occasions. I have worn them everywhere from hiking Northern California’s Mount Tamalpais to walking through the streets of Europe. They are comfortable and have a very rounded toe so don’t put pressure on my feet!


Earth Origins Nessa {Buy it Here}

Cute & Comfortable Travel Boots for Women Walking the World


Sam Edelman Tinsley Rain Boot {Buy it Here}

Cute & Comfortable Travel Boots for Women Walking the World


Sole Society Natasha {Buy it Here}

These casual and slip-on booties are my favorite for small European cities and beyond (I was in Montana in the photo). They are suede which can pair perfectly with several different looks, a pair of casual jeans or cargo pants are my favorite things to wear them with.


JBU Parker Boot {Buy it Here}



Hush Puppies Women’s Dorris Fairley Ankle Boot {Buy it Here}


UGG Leigh Boot {Buy it Here}

These are my go to boots for almost all cold-weathered trips! I love the height that will keep my calves warm, which is particularly helpful when I wear them with a skirt. Plus, the color matches many items and also stands out compared to the traditional black. Don’t forget to add some cute boot socks for extra style!


Western Distressed Cowboy Bootie {Buy it Here}


Circus by Sam Edelman Kilbourn Fashion Boot {Buy it Here}


Dansko Women’s Lola Ankle Bootie {Buy it Here}


Rocket Dog Sayla Vintage Worn Western Boot {Buy it Here}

These western inspired boots 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 on the Palace on Wheels luxury train through India and wore them at every stop.


Born Kerri Bootie {Buy it Here}

20 Cute & Comfortable Travel Boots for Women Walking the World


Naturalizer Jessie Wide Calf Boot {Buy it Here}

20 Cute & Comfortable Travel Boots for Women Walking the World


UGG Women’s Aureo Ankle Boot {Buy it Here}

Cute & Comfortable Travel Boots for Women Walking the World


Born Womens Cross Boot {Buy it Here}

Cute & Comfortable Travel Boots for Women Walking the World


Naturalizer Women’s Zeline Ankle Bootie {Buy it Here}

20 Cute & Comfortable Travel Boots for Women Walking the World


Dansko Women’s Veronica Ankle Bootie {Buy it Here

20 Cute & Comfortable Travel Boots for Women Walking the World



Rieker Women’s Bernadette Boot {Buy it Here}

20 Cute & Comfortable Travel Boots for Women Walking the World

Annette White walking through Tokyo's Piss Alley

Don’t think that because you are traveling you will have to sacrifice cuteness for comfort. You can absolutely have both.

What are your favorite travel boots that are made for walking? Leave your picks in the comments.


Related & Helpful Resources

20 Cute Travel Inspired Jewelry Accessories
15 Cute Winter Jackets Fit for Travel

2018-10-26T16:19:53+00:00October 26th, 2018|Categories: BEAUTY & STYLE, LIFESTYLE|Tags: , |

3 Comments

  1. Nakisha William October 11, 2017 at 8:06 pm - Reply

    Thanks for Listings Boots. Is it best enough to purchase Sole Society Natasha Boot for daily walking and also for the stylish look?

  2. Choi Rose October 12, 2017 at 3:21 am - Reply

    Just – awesome!

  3. Leslie Hamilton November 5, 2017 at 3:24 am - Reply

    What a listing! These are stylish.

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