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We’ll never tire of the classic outdoor recreation aesthetic—give us made in USA 60/40 parkas, wool pants, and chunky sole, laced-to-the-toe 1970s hiking boots all day. But the issue with living in the past is that there’s never anything new. Sure, we could amass an entire collection from eBay and vintage sellers worldwide, but production capabilities have come quite a ways since the ‘70s and ‘80s. Plus, it’s not always so easy to track down that grail piece in your exact size and color choice. That’s part of the fun in collecting vintage, but it’s not everyone’s thing.
There is a best of both worlds though, and hiking footwear is one category where you might've noticed new styles channeling vintage men’s and women’s style hiking boot roots, while adding contemporary touches. Cushier soles, better waterproof construction methods, funkier colorways, responsibly sourced leather; we’re not skating around on hoverboards yet, but we’ve got some pretty great hiking shoes.
By balancing form and function, this breed of vintage style hiking shoe keeps classic outdoor style alive. From breakout and established brands alike, there are plenty of retro boots to choose from (and not all of them are old school hiking boots with red laces). Keep scrolling for our top picks.
The 10 Best Classic Hiking Boots Made for Modern Life
Not much has changed for the Mountain Light in the forty-plus years since Danner began handmaking them at its Portland, Oregon factory. This style is the grandaddy of several lifestyle spin-offs introduced by the brand over the years, so check those out if black or brown doesn’t cut it. Thick, full-grain leather uppers with a Gore-Tex waterproof membrane sit atop a heavy-duty Vibram outsole with traction for days. With a pair weighing in at 58 ounces, they’re by no means a lightweight boot (despite the name) but are fully capable of your next backpacking trip, once you break them in.
American bootmakers Vasque created an instant classic when they released the Sundowner boot in 1984. A cleverly named update dubbed the Sunsetter retains much of the original flavor of the original Sundowner and other vintage Vasque hiking boots while injecting some 21st Century tech. The Sunsetter's uppers have made the switch to a waterproof suede leather, and are made from 50% recycled materials and lined with a 100% recycled interior fabric. Ankle support comes from a molded mesh collar with a cushy midsole providing comfort at the base. They truly offer the best of vintage Vasque hiking boots, and the tan “lion” colorway perfectly executes the classic old-school hiking boots with red laces look. (For more of a retro hiking shoe vibe, check out the equally iconic Vasque Clarion 88.)
We’re pretty big fans of the high-style and highly rugged boots Italy’s Diemme puts out. Though the style of the Roccia Vet fits well into the vintage style hiking boot world, its origins are actually as a hunting boot. A lighter weight sole makes it an ideal candidate for daily wear, but there’s no shortage of lugs down there for traction for Winter or rough terrain. Vegan wearers will appreciate the synthetic Cordura upper, and everyone should like this vintage style hiking boots' wraparound rubber guard, which protects from abrasions.
The French Tyrolean shoe specialists at Paraboot are known best for their stylish Michael shoe, but the brand's catalog packs some heavy-duty gems like the climbing-inspired Yosemite boot. Handcrafted in Spain, the leather boot's textured rubber mudguards protect the luxe material while providing a touch of rugged hiker style. Thick rubber lugged soles are sure to provide plenty of traction for everyday and casual wear while still lending some bounce to your step. The blue colorway is undoubtedly the favorite, but more somber palettes are available.
After a dip into the world of fashion, we found this reasonably conventional boot from California designer Reese Cole. Production of the line’s apparel takes place in their hometown of Los Angeles, but Italian bootmakers take care of the vintage hiking boot-inspired Wilson. Immediately noticeable is its extra D-ring located at the heel, which we’re pretty sure serves no functional purpose other than style. The brand encourages wearers to lace the suede boot however they feel though, and even includes three pairs of shoelaces for further customization and color combos.
Italian bootmaker AKU has fused alpine DNA into the moderately capable Slope Original GTX, which is suitable for regular wear or light trails with grip from a Vibram sole. A combo of suede and proprietary fabric makes up the boot uppers, and of course, you’ll find Gore-Tex taking care of waterproof membrane duties. The palette of brown, yellow, and green could prove tricky to coordinate into your fit, so please drip with caution.
With over a hundred years of experience making long-lasting and reliable work boots, the Canadian brand knows a thing or two about design. The Skogan, first introduced in 2021, takes inspiration from old school models the brand made back in the 1980s—though the construction of the Skogan is all modern. As the most “environmentally considered boot in the history of the company," the Kodiak Skogan features a textile upper composed of 100% recycled plastic, laces made of 50% recycled material, and lining made of 100% recycled plastics.
The Seattle-born outfitters reach way back into their 1964 catalog to reintroduce the K-6 boots for 2023 hikers and outdoor style enthusiasts, who have a choice here between brown and black leather in the ankle height, weatherproof lace up. On the brown leather option, a pair of work boot laces add a welcome change from the typical red, while the black colorway adds a pop of color with electric blue lacing. No matter which stylish colorway you go for, a black Vibram sole will have you finding traction anywhere it’s needed.
Retro and vintage may be subject terms, so let’s instead refer to the iconic beef and broccoli boots as “classic.” If it’s not obvious, the lace up ankle boots receives their street name from the full-grain brown leather paired with a deep green canvas that imitates the palette of the Chinese take-out staple. Timberland’s own TimberDry membrane keeps feet bone dry while sourcing 50% of its materials from recycled sources, a win for dry feet and the environment alike.
The American casualwear retailer might not be the first place you’d look for a hiking boot, but these brown suede clompers serve heavy mountaineering boot style with a sturdy, lugged rubber outsole from the experts at Vibram. Thick red shoelaces continue the retro trend and a heavily cushioned ankle provides comfort during strolls down the street or trekking in the backcountry with style.