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9 Stylish Boots You Can Actually Walk In

Travelers shouldn’t have to choose between stylish boots and ones that will destroy your feet a mile in. These picks will keep you warm, comfortable, and looking good.

Merrell Tremblant Ezra Tall Waterproof Ice+

In the winter, anti-ice treatments often leave a salty white coating on your winter boots. To prevent this, Merrell’s new Tremblant boots are treated with a salt-resistant coating that prevents your boots from getting that dirty salt rim. Inside the Tremblants, Merrell’s Select WARM 200-grams insulation (plus a faux fur lining) will keep your feet and calves warm.

These boots are comfortable to walk in, with a Vibram Artic Grip outsole that provides solid traction on ice or wet surfaces, and Kinetic Fit Base, a removable contoured insole, for customized support.

Cole Haan Harrington Grand Riding Boots

Cole Haan’s Harrington Grand Riding Boots are the rare pair of stylish boots that are actually comfortable to walk in. The Harringtons are an updated, modern take on the riding boot style, and come in rich black or brown leather to match any outfit. The inside is lined with a breathable man-made material, and features a padded footbed that offers support and cushioning.

SOREL Whistler Tall Boots

Headed somewhere really cold? Pack the SOREL Whistler Tall Boots, which are rated to a temperature of -25 degrees, thanks to a 200g insulated interior and wool lining inside. The boots are also completely waterproof and will stay dry even in heavy snow.

These stylish boots will go with any winter outfit, and are extremely comfortable to walk in, even in slippery conditions.

Timberland Men’s White Ledge Mid Waterproof Ankle Boot

Timberland’s White Ledge boots are the perfect height – low enough to make them easy to pack, but high enough to keep you dry in most snow conditions. The boots are seam-sealed for complete waterproofing, and feature a speed lace design that makes them easy to take on and off at airport security.

BZEES Boomerang Tall Shaft Boot

BZEES Boomerang Tall Shaft Boots feel like wearing slippers, thanks to their patented free-foam memory foam footbeds and air-infused outsoles. The boots are very lightweight and easy to pack. The upper is made of a stretch material that folds down, so these pack more like shoes than boots. A side zip closure and stretch bungee cord at the top of the boots allow you to adjust these stylish boots for a custom fit.

SAS Delaney Ankle Boots

SAS’ Delaney Ankle Boots are perfectly designed for travel. The ankle booties will fit in a small carry-on, but they’re so comfortable and easy to slip on and off that you’ll want to wear them on the plane. The boots are handcrafted in Italy using buttery and long-lasting Italian. Elastic gore side panels offer a flexibility that will fit your feet even if they are swollen from your travels.

These classic boots look good with jeans or a dress, and are incredibly comfortable to walk in, thanks to a cushioned insole.

Kamik Greenbay Cold Weather Boot

Kamik’s Greenbay boots work for any temperature, thanks to the removable thermal liner, which you can insert or take out depending on the weather. The outside is waterproof, and a drawstring at the top of the boot helps keep rain or snow out and can be adjusted to fit any size calf.

Propet Madison Tall Boots

Walking shoe company Propet has taken their orthopedic technology and put it in a winter boot.  The Madison Tall Boots feature a unique heat-retaining insole, and a scotchgard treated exterior, which will keep your feet warm and dry.

Dream Paris Boots

These mid-calf boots by Dream Paris feature a secret pocket to store your cash and credit card. The affordably priced boots start at $34.99 and come in nearly 20 different colors, so you can get one to match every outfit.

More from SmarterTravel:

Caroline Morse Teel loves stylish boots for cold weather travel. 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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