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Stylish Walking Shoes for Travel

12 Shockingly Stylish Walking Shoes for Travel


Comfort or style? You don’t have to choose between the two with these pairs of ultra-comfortable walking shoes for travel that are actually stylish.

Sperry Captain’s CVO Sneaker

Sperry captain's cvo sneaker

Sperry’s classic sneaker design gets an update in the new, lighter-weight Captain’s CVO sneaker. With features like a flexible slip-resistant outsole, a supportive removable footbed, and a soft blister-resistant lining, you won’t even need a breaking in period. You’ll be able to walk for miles right out of the box. The unisex, classic design works with everything from shorts to dresses.

Reef Iris Sneakers

Reef iris sneaker

So many fashion shoes lack support, but Reef’s Iris Sneakers are outfitted with anatomical arch support that will keep you comfortable all day long. These stylish walking shoes are perfect for travel, with a slim profile that’s easy to pack and looks good with almost any outfit. Made from a canvas twill, these sneakers are easy to clean, and also, thanks to elastic detailing, easy to slip on and off.

Cole Haan ZEROGRAND Explore Waterproof Hiker Boots

Cole haan zerogrand explore
Cole Haan

Cole Haan’s ZEROGRAND Explore Waterproof Hiker Boots are unbelievably lightweight, weighing around 12 ounces each. These boots are waterproof, warm, and mix outdoor-friendly technical features (like a slip-resistant outsole) with urban style. The lightweight and Grand.OS cushioning technology in these boots mean your feet and legs won’t tire as easily. These boots are the rare piece of footwear that will work whether you’re tackling a trail or just taking a walk downtown.

Seavees The Legend Sneaker Standards

Seavees the legend sneakers

The classically cool SeaVees the Legend Sneaker Standards make an excellent walking shoe for travel. The casual sneaker is made from a smooth poplin twill material that keeps your feet from overheating. Although these shoes look casual, they have some serious comfort features like a contoured foam footbed and molded grip-lock outsole. The Legends come in men’s and women’s versions and in a wide range of colors, from classic white to lavender.

Keen Elsa III

Keen elsa iii sneaker

Keen has updated their best-selling Elsa sneakers into a new version with a cushioned Luftcell footbed, padded heel panel, and plenty of stylish color options. The Elsa III’s canvas material is lightweight and breathable.

Samuel Hubbard Hubbard Free

Samuel hubbard free

If you can only pack one pair of shoes for your trip, the Hubbard Free should be it. Nicknamed the “Unsneaker” Samuel Hubbard’s Hubbard Free is a hybrid between a casual shoe and a dress shoe and promises to handle any travel-situation from a long walk to a nice evening out. They are also some of the most comfortable shoes you can buy, designed with buttery-soft full glove-leather lining, custom Vibram soles, triple-density leather lined memory foam insole, and a lightweight Kevlar shank for arch support.

Yosi Samra Samara Flats

Yosi samra flats

Packable ballet flats are often flimsy and unsupportive, but not Yosi Samra’s. These fold-in-half flats are easy to pack in a purse or carry-on and they have a plush memory foam padding in the toe and heel areas. The Samara Flats weigh a mere four ounces and come with a compact carrying bag.

adidas Outdoor Terrex Parley

Adidas terrex shoe
Adidas Outdoor

The Terrex Parleys are true boat shoes. With a special drainage system to quickly move water out and a Traxion outsole that offers excellent grip even on wet surfaces, these shoes were designed to be on deck. And not only are they good on the water, but the Parleys are good for the water. Made with yarn that uses Parley Ocean Plastic, which is created from recycled waste from coastal communities, these shoes are doing their part to keep the ocean free of plastic.

Merrell Ontario Mid Waterproof

Merrell ontario mid waterproof boots

Hiking shoes that you can wear on and off the trail? Merrell has made the impossible possible with their new Ontario Mid Waterproof boots. Available for men and women, you can wear these stylish boots with either jeans or hiking pants.  You’ll get a lot of miles out of these shoes, thanks to an air cushion in the heel that absorbs shock, and the Vibram Megagrip soles will keep you stable no matter what the terrain.

Vionic Thatcher Boots

Vionic thatcher boots

The low-heeled Vionic Thatcher Boots feature built-in orthotics for the ultimate in comfort and walking support. These leather booties are water-resistant, so you can safely take them out in the rain. And if you’re wearing the Thatchers at the airport, you’ll appreciate the back loop that makes them easy to put on and take off in the security line.

Sanuk TKO

Sanuk tko shoes

Sanuk’s TKO shoes have a casual design that will pair well with shorts or jeans. They look super casual, but these shoes sneak in plenty of comfort on the inside. With a molded EVA footbed that uses an antimicrobial additive to reduce odors and outsoles that are removable for easy washing, or in case you’d like to swap in your own, these stylish walking shoes offer a lot of bang for your buck.

Sperry Oasis Canal Boat Shoe

Sperry oasis canal shoe

Sperry’s Oasis Canal Boat Shoe are slip-on shoes made from premium leather lined with moisture-wicking technology to keep your feet dry, blister-free, and fresh. Although these look like normal boat shoes, they have a hidden memory foam insole that offers arch support and padding without adding weight.

What to Wear on Your Next Vacation

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Caroline Morse Teel loves the new stylish walking shoes trend. Follow her on Instagram @TravelWithCaroline for style and travel photos from around the world. 

Some review products are sent to us free of charge and with no incentive to offer a favorable review. We offer our unbiased opinions, positive and negative, and will never accept compensation to review a product.

We hand-pick everything we recommend and select items through testing and reviews. Some products are sent to us free of charge with no incentive to offer a favorable review. We offer our unbiased opinions and do not accept compensation to review products. All items are in stock and prices are accurate at the time of publication. If you buy something through our links, we may earn a commission.

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