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Trailblazers: 10 Best Vintage Hiking Boots

Hiking boots are much better now than they were even five or ten years ago. Yet, it is hard not to pine after the old-school hiking gear of yore. Rather than having a high-tech rubberized feel that so many hiking boots do now, older boots embraced leather materials, simple silhouettes, tough construction, and natural waterproofing provided by seamless uppers.

Thankfully, there are still boots being made today that embrace that more traditional look. Even better, a lot of those boots have been combined with newer technology – making it so they not only look good but feel great even on long hikes through the backcountry. Whether you are looking for a sturdy pair of hikers for taking on serious treks, or just a solid pair to wear in the city during the colder months – we’re sure you’ll be satisfied with our roundup of the best vintage hiking boots for men.

Vasque Sundowner

You don’t have to break the bank in order to sport some cool vintage hiking boots. This pair from Vasque boasts an American-made leather construction from Red Wing, a GORE-TEX lining for waterproofing, and both a gusseted tongue and polyurethane midsole for superb comfort. For a little bit of style, the leather upper (which comes in either suede, black, or red oak) is contrasted by a metallic D-ring lacing system. An altogether solid pair of boots that’ll be good for years of use.

Purchase: $130

Sorel Ankeny Waterproof Leather Boots

These boots don’t necessarily scream ‘vintage’ like others on this list. Rather than boasting a seamless leather upper, these feature a rubber toe and heel-cap that you’d never see on anything from the 1970s or before. That being said, these do benefit from a simple, and attractive construction. The upper is made from a waterproofed leather that’s been seam-sealed with a vulcanized rubber sole. For extra comfort, the boots have been fitted with a removable EVA footbed making them a great pair for braving a wet fall or slushy winter.

Purchase: $140

Timberland 1978 Hiker Waterproof Leather Boots

These boots feature the exact same design as Timberland’s original mountaineering boots released almost 40 years ago, but with some substantial updates. Along with the seamless waterproof upper, these hikers have a proprietary Timber-Dry waterproof membrane as well as a deeply lugged Vibram rubber outsole. For added comfort, the boots have been fitted with footbeds designed to take on both ascents and descents. Oh yea, and they look incredible.

Purchase: $250

Fracap M120 Ripple Sole Scarponcino Boot

Our first few picks have solid North American roots. In contrast, this pair of vintage hiking boots from Fracap are proudly handmade across the pond in Italy by some of the most skilled craftsmen out there. This particular style from Fracap is their most popular silhouette. Seeing that it’s made from a high-quality Italian leather, features a D-ring lacing system, and has a classic ripple sole – we can see why.

Purchase: $275

Grenson Brady Suede-Panelled Leather Boots

These vintage hiking boots are definitely capable of going off the beaten path – but you’d likely not want to take them all too far in that direction. Featuring XL EXTRALIGHT rubber lug soles and an upper made from a combination of high-quality leather and suede they’re the perfect pair of boots for wearing during the colder time of the year.

Purchase: $335

Danner Mountain Pass

Few boot makers have managed to combine old-school looks with contemporary hiking technology better than Danner. The outdoor gear brand has been around since the early 20th century, making boots for loggers, the military, police, and outdoor enthusiasts alike. Their Mountain Pass boot is by far one of their most popular – and for good reason. They feature a full-grain leather upper, a GORE-TEX lining to keep your feet dry no matter what, and a sturdy Vibram Kletterlift outsole. All of these features and more come together to make a totally capable boot. And to top all of that off, they’re made by hand in Portland, Oregon.

Purchase: $360

FEIT Hiker Shearling-Lined Boots

Like Danner, FEIT makes all of their shoes by hand. Unlike Danner, FEIT makes their boots outside of the U.S., and they’re not quite built for hard wearing. Instead, these vintage hiking boots are more aimed at the guy looking for a pair of incredibly stylish boots for wearing in the city during the winter. The upper of the boot is made from a high-quality vegetable tanned leather and is lined with a warm, plush shearling that’ll keep you from losing feeling in your toes. The deep-lugged Vibram Gumlite outsole is Goodyear-welted to the upper and purpose-built for trekking on wet and icy surfaces.

Purchase: $760

Moncler Peak Pebble-Grain Leather Hiking Boots

These boots, like the last, are maybe better fit for lighter wear than they are for taking out on long, strenuous hikes. Made from an incredibly fine scuff-resistant Italian pebble grain leather fitted with a padded collar and attached to a Vibram outsole, they’re definitely capable of wearing out on a ski trip, or around the city. To top off the quality materials, the midsole is colored red, white, and blue at the heel to match the laces snaking through the D-rings on the shoe’s upper.

Purchase: $765

Heschung Richmod Pebble-Grain Leather Hiking Boots

If having a pair of vintage hiking boots isn’t quite stand-out enough for you – then you should consider this pair from Hechung. Not only do they boast an old-school silhouette, but the French boots boast a beautiful pebble-grain leather upper, a buckled strap, and bright red laces that snake through a series of metal clips running up the shoe’s tongue. They’re even nice enough to include in your office wardrobe.

Purchase: $800

Ralph Lauren Purple Label Boots

Contrary popular belief, you don’t need to have conquered the Pacific Crest Trail or the Appalachian Trail to need to throw on a pair of boots as well built as this pair from Ralph Lauren. Made from a gorgeous leather-trimmed suede upper and finished off by a Vibram Gumlight sole, these old-school hiking boots from the famous designer are ideal for trudging around the ski resort or for a walk to work during the cold winter months.

Purchase: $1,500

20 Best Hiking Boots For Men

Looking for a newer model of hiking boots for your next adventure in the backcountry? Take a look at our list of the 20 best hiking boots.