The Most Stylish Men’s Boots: Waterproof, Lace-up, Hiking, and More

By Katie Fish
March 06, 2018
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Seasons typically dictate what we wear on a day-to-day basis. Rain jackets are for spring, shorts are for summer, sweaters are for autumn, and scarves are for winter.

But there are a few pieces every stylish and well-balanced travel wardrobe needs: items that can transition throughout seasons (and locations) like T-shirts, jeans, lightweight jackets, and boots. While boots may not be the first item that comes to mind when you think of a year-round, all-destination wardrobe staple, think again.

Related:10 Comfortable Dress Shoes for Men

Unlike other shoes — like sandals and thin canvas sneakers — boots are the perfect transitional travel shoe. They offer support to both the ankle and the sole, making them ideal for those long days spent on your feet.

Boots can also be dressed up or down depending on the occasion. You can easily pair them with a nice trouser for a night out in a new city, or wear them with comfy sweats at the airport.

We have rounded up the most stylish boots for all of your upcoming travels. Some pairs offer waterproof design, which is essential for rainy locations or unpredictable climates, while others offer an extra comfortable, cushioned sole for all-day wear.

Ahead, 12 pairs of stylish men's boots that blend fashionable design with technical function.
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Chelsea Boot: Dr. Martens

Courtesy of Zappos

Removing your boots in the airport security line just got a whole lot easier because of the elastic gore panels on these Chelsea boots.

To buy: zappos.com, $165

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Brown Lace-up Boot: Wolverine

Courtesy of Wolverine

The cushioned wedge sole on these work-inspired boots provides extra comfort for a long day on your feet.

To buy: wolverine.com, $285

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Waterproof Boot: Cole Haan

Courtesy of Cole Haan

For a taller boot option, opt for this waterproof leather and waxed canvas pair from Cole Haan. It's got a pull-tab that makes it easier to get back on post-TSA check.

To buy: colehaan.com, $150

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Chukka Boot: Clarks

Courtesy of Zappos

The historic Chukka boot was originally meant for British soldiers stationed in Northern Africa during World War II, but the practical design stuck and is still popular today. And Clarks has perfected the style, crafting it with natural materials for maximum comfort and mobility. They're also Anthony Bourdain's favorite shoe to travel in. 

To buy: zappos.com, $130

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Dress Boot: Ecco

Courtesy of Zappos

The regal wingtips on these breathable boots will take you from day to night, and with Ecco's proprietary Fluidform technology, these shoes provide cushion and rebound with every step you take.

To buy: zappos.com, $250

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Hiking Boot: Eddie Bauer

Courtesy of Eddie Bauer

These stylish adventure boots have a stabilizing heel, exceptional grip, and look just as good on mountain trails as they would during a country weekend away.

To buy: eddiebauer.com, $140

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Brown Boot: Frye

Courtesy of Zappos

These simply designed brown suede boots have both a luxurious look and feel, thanks to a cushioned footbed.

To buy: zappos.com, $164

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Black Boot: Topman

Courtesy of Topman

The rubber sole on these 100 percent leather boots will keep you in line on all types of terrain throughout your travels.

To buy: topman.com, $99

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Casual Boot: Toms

Courtesy of Toms

Because of Toms' “One for One” business model, you can give the gift of comfort and ease to someone in need and by purchasing a pair of these fashionable boots for yourself.

To buy: toms.com, $89 (originally $150)

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Snow Boot: Sperry

Courtesy of Zappos

Packing for a snowy trip? Bring these duck-inspired Sperry boots that are not only waterproof, but also have a lugged sole for extra traction, and a stain-proof upper, as well.

To buy: zappos.com, $140

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Winter Boot: Ugg

Courtesy of Ugg

Ugg has made the ultimate winter boot with this fully lined pair that feels like you're stepping into slippers. Despite being wind and waterproof, they are also incredibly breathable so your feet won’t overheat.

To buy: ugg.com, $130

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Rain Bootie: Stutterheim

Courtesy of Stutterheim

Finally, a fashionable rain boot for men. These Stutterheim booties are attractive enough to wear even when it’s not raining, and the thick lug sole will help with traction when it is.

To buy: stutterheim.com, $145

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