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

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

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

To buy: wolverine.com, $285

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

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

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

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

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

To buy: zappos.com, $164

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

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)

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

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

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