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.