The 12 Best Travel Boots for Men

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In Terry Pratchett’s 1993 novel Men At Arms, Captain Samuel Vimes has a theory about boots: By investing in a more expensive pair, you’re actually getting a better deal since they’ll last longer than a cheaper pair. This has become my ethos when I’m choosing any footwear, but never more so than when I’m looking for a pair of travel boots.

The ideal travel boots should be able to take you anywhere you want to go, from dining in a restaurant, to walking all day on city streets, to heading off road for a walk on dusty trails. They should look good, wear comfortably, and be built to last for years, not months. And I genuinely believe that the 12 pairs listed here are the best travel boots for men, with each having their own special qualities that set them apart.

Beckett Simonon Medina Boots

Beckett Simonon Medina Boots

A direct-to-consumer business model lets Beckett Simonon offer top notch, handmade leather footwear at a small fraction of the price you’d expect to pay. By removing the middleman, they connect artisans in Colombia directly to the United States and abroad—meaning that you reap the benefit of handmade-to-order boots, with some of the finest attention to detail I’ve seen in a footwear brand. More than 150 manual design and construction steps means these boots will take about six weeks to get to you, but let me tell you it is absolutely worth the wait. Add in a meticulously crafted sole construction that’s easy to replace when it’s worn, and you get a pair of traveling boots that you can put thousands of miles on.

Danner Vertigo 917 Boots

Danner Vertigo 917 Boots

Portland, Oregon based Danner Leather Co. knows a thing or two about boots. They’ve been crafting new and classic styles of their ever-popular leather footwear for over 90 years, giving them a perspective on the industry that’s constantly innovating while sticking to the traditional details that made them a success in the first place. Their Vertigo 917’s are a real standout as a travel boot, falling somewhere between the comfort of a sneaker and the rugged durability of a boot. Waterproof and breathable Gore-Tex liners add the finishing touches, keeping your feet dry and comfortable no matter the weather.

All-Weather Duckboot

All-Weather Duckboot

Lightweight construction combines with 100 percent waterproof construction and grippy Vibram outsoles to make the All-Weather Duckboot a perfect boot for exploring, whether in the city or on the trail. A Huckberry exclusive, it’s built to offer the durability and protection of a boot with the easy-wearing performance of a tennis shoe. Think of it as an upscale version of the classic duckboot design, with full-grain leather giving it a restaurant-ready appearance and a cushioned EVA midsole making it suitable for all day, every day wear.

Vivobarefoot Tracker II FG Mens Boots

Vivobarefoot Tracker II FG Mens Boots

Ever wanted to get rid of your shoes, and really feel the ground beneath your feet? Ground hazards like rocks, glass, and trash make that inadvisable, but you can still get that same feeling with Vivobarefoot’s boots. Designed in a barefoot style, they’re minimally cushioned and meant to keep your feet connected with every bump and curve of the terrain. Their Tracker II FG boots are especially good for traveling, as they’re classy enough to fool people into thinking you’re not basically barefoot and wearing hiking boots. They’re waterproof and breathable too—just one more way that they feel close to wearing no shoes at all.

SeaVees Maslon Desert Boot

SeaVees Maslon Desert Boot

The rugged oiled leather of SeaVees’ Maslon Desert Boot is like a hug from an old friend, but for your feet. From day one, they’ll feel like the best pair of broken-in boots—minus the wear on the sole that comes with extended use. The mid-cut chukka design and natural variation in the leather make them a handsome pair of boots, too, perfect for wearing from city streets to dusty trails. A contoured foam footbed makes them comfortable enough to wear all day, and a herringbone grip outsole means you’ll have sure footing even on wet sidewalks.

New Republic Ventura Leather Chelsea Boots

New Republic Ventura Leather Chelsea Boots

If your idea of adventure is more in line with exploring New York or Chicago than heading into the mountains, a pair of boots like New Republic’s Ventura Leather Chelsea is an excellent fit. They sport what might be the classiest look of any travel boot featured here, but they definitely don’t skimp on comfort and durability to do so. Premium full grain Italian leather uppers are the real draw here, with a natural ability to take a refined patina with extended use. EVA midsoles help them break in quickly and stay comfortable longer, and the stacked leather sole is finished with a rubber bottom tread for enhanced grip and stability.

Greats The Wooster Hiker Boot

Greats The Wooster Hiker Boot

For eye-catching looks with your hard-wearing boots, look towards The Wooster from Greats. Built in a streetwear-ready style, it’s high-contrast laces and hardware really make the full grain pebbled leather pop. But it’s not all show and no go for these boots — a padded antimicrobial footbed keeps your feet snug, comfy, and fresh, and a vulcanized outsole gives added grip in slippery conditions. Combine that with a padded collar for ankle-level comfort, and you get a boot that looks as good as it feels and is made to last for years.

Timberland Squall Canyon Waterproof Chelsea Boots

Timberland Squall Canyon Waterproof Chelsea Boots

Chelsea boots are great for quickly pulling on to run an errand, but they often fall victim to being less than comfortable in poor weather. Timberland’s Squall Canyon Boots fix this problem by making the entire boot waterproof, then adding a grippy rubber outsole to keep you upright no matter how slick the streets might be. Their proprietary MirrorFit sole system helps the boots immediately conform to the unique shape of your foot, giving you support exactly where you need it. Combined with OrthoLite comfort foam’s antimicrobial properties, this makes the Squall Canyon boots a darned good fit for just about anyone.

Nike SFB Gen 2 8” Gore-Tex Tactical Boots

Nike SFB Gen 2 8” Gore-Tex Tactical Boots

When outdoor adventure calls and you must answer, a pair of tactical boots like Nike’s SFB Gen 2s are just what you need. Designed for speed, flexibility, and agility, they’re equipped with dual-zone lacing for a locked-in fit and an integrated rock shield to protect the soles of your feet. Gore-Tex inner sleeves keep them waterproof but breathable, and a rubber outsole with reinforced heel strike zone caps off their all-purpose ruggedness. Add in a little Thinsulate insulation for cold weather wear and a durable foam midsole, and this boot is prepared for anything.

Columbia Fairbanks Rover 2 Boots

Columbia Fairbanks Rover 2 Boots

Wintertime travel demands a lot of changes in your wardrobe—especially in your choice of footwear. But most winter boots are big and clunky, and far from anything you’d like to wear to a nice dinner. Columbia’s Fairbanks Rover 2 Boots buck the trend, offering top notch insulation and waterproofing with a sleek, refined design and all leather uppers. 200 gram insulation combined with a breathable liner will keep your feet warm and dry, and the Omni-Grip traction rubber soles will let you keep your footing even in icy conditions. That’s all topped off with a Techlite midsole that offers best in class comfort, excellent durability, and high energy spring-back return with every step.

Adidas Superstar Boots

Adidas Superstar Boots

You don’t have to sacrifice bold style for rugged durability in your travel boots, and Adidas’s Superstar Boots prove it. Modeled after the aesthetics of Adidas’s most popular sneakers, they pop with a mid-cut design made of full grain leather for long-lasting durability. A synthetic outsole provides good grip on most surfaces, and metal quick-lace hardware makes them fast to put on and take off. If you want a pair of boots that you can feel fly wearing just about anywhere, the Superstars will get you there.

Lems Boulder Boots

Lems Boulder Boots

For anyone looking to put in a lot of hiking miles on their travels, the zero-drop design of Lems’ Boulder Boots is a godsend. By not elevating your heel and giving you a wide toe box, your foot can take its natural shape and stay healthy no matter how long you walk. The 1200-denier nylon and nubuck leather uppers are breathable and water-resistant, all while being quick drying in case you get caught in a downpour. Injection blown rubber outsoles are incredibly flexible, too, letting you pack down the Boulder Boots into a tiny ball for easy storage on the road.

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