My Tip: Stop sacrificing luggage space for too many shoes! These are 11 of my best travel shoes for the Fall and Winter seasons that will allow you to explore a new city all day, every day, without pain.
I have walked a lot of cobblestoned streets in my travels, and these all stand the test! These shoes have great arch support, are comfortable enough to wear all day, and are all waterproof.
I have to pack in only carry-on luggage, so choose 2 to pack from this list based on you and your weather during vacation.
Boots
I love a good boot, and these four pairs will make you feel fashionable while keeping your feet dry. These boots feel like sneakers, which is a win in my book!
The Sneaker-Feel, Water-Resistant Boot
This boot provides a solid footing for walking on rough, cobbled streets thanks to its rugged sole. The best part? It genuinely feels like a sneaker. It features a strong, stretchy elastic and an easy-to-manipulate zipper, allowing your foot to slide in effortlessly. You may want to size down half a size for the perfect fit; there is still room to add your favorite arch support inserts.
Versatile Mid-Calf Waterproof Boots
These are incredibly comfortable and are completely waterproof. With only about a 1-inch heel, the sole offers a solid, dependable step for long walks. A feature many travelers love is that they are loose around the middle of the calf (mid-calf height), making them easy to wear over travel jeans or trousers.
Chic Waterproof Ankle Booties
These cognac low-heel ankle booties are a favorite, and work perfectly through Fall and Winter. They are waterproof and feature a stretch section right above the ankle, designed not to cling to your skin. They run a tad big. I ordered my true size and used arch support inserts to ensure a snug and custom fit.
Cold-Weather Columbia Boots
If you are headed anywhere with very cold temperatures or snow, these are a must-pack. These Columbia boots are completely waterproof and, unlike older, clunky styles, they feel light and comfortable—like a tennis shoe. They are very supportive and feature a great, rugged sole.
Sneakers
These sneakers can handle multiple miles and did not leave my feet sore the next day.
The Fully Waterproof Walking Sneaker
This sneaker is incredibly comfortable and completely waterproof. It’s a great choice for tackling the tricky spacing of European cobbled streets, thanks to its wide foot base and arch support. A small detail to love is the smooth laces, which make loosening them easy.
The Rugged On Cloud Waterproof Shoe
If headed on a river cruise, this running shoe is a great choice; it’s completely waterproof and features a rugged sole and stretchy laces. They are very comfortable on their own, but like many travel shoes, they have enough room to add your preferred arch inserts for maximum support.
The Supportive Ecco Travel Shoe
Ecco has a supportive, comfortable, and water-resistant shoe that is worthy of a top recommendation. The all-around support and quality construction make this a reliable choice for long days of touring. I especially like wearing these between seasons with cropped pants.
Project Cloud Arch-Support Sneaker
These are a cute, comfortable, tennis-shoe style option with good arch support for excurions. They feature a substantial tennis shoe sole, but they are not water repellent. The main tip for these is to size up half a size to avoid the hassle of returns. The patterns are adorable!
Skechers for Easy Travel
Skechers are an affordable and comfortable option for all travelers. Skechers offers two great options for travelers: a leather-look, water-repellent boot for fall, and a dedicated waterproof snow boot. If you like a simple slip-in feature, Skechers often has that. Be aware that Skechers often runs large, so you may need to size down half a size.
Travel Hacks for All-Day Foot Comfort
Now that you have your perfect waterproof shoe or shoes picked out for your trip, let’s talk about how to pack them!
The Power of Arch Support Inserts
Whether or not your shoe already has support, it is a crucial travel tip to pack never-flatten arch support inserts.
- They come in men’s and women’s sizes.
- They can be cut to fit the width of any specific shoe.
- They are available in three different heights for your arch (I recommend the high arch option).
If you are concerned about arch inserts or other bulky shoes taking up space, simply pack them inside your compression cubes to minimize volume.
Smart Shoe Packing Hack
To maximize space and keep the rest of your clothes clean, follow this shoe packing hack: use a simple produce bag or newspaper bag to pack your shoes.
The trick is to separate your shoes (left foot in one area, right foot in another) rather than packing them together. This will open up much more space in your luggage!