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Men's Trail Shoes

Explore men's trail shoes and compare styles, sizing and fit to find the right pair for you. Review each shoe's product details to narrow your choices based on the features that matter most to you.

Men's Oboz Bridger Low B-Dry Hiking Shoes
Oboz Men's Oboz Bridger Low B-Dry Hiking Shoes
A gray waterproof leather hiking shoe with cushioned support, protective toe caps and durable trail traction.
(279)
$175 $175
SALE
What customers like:
Durable construction
High-quality materials
Superior arch support
Comfortable fit
Professional customer service
$175 $175
SALE
Men's NextVenture Hiking Shoes, Waterproof
L.L.Bean Men's NextVenture Hiking Shoes, Waterproof
Waterproof hiking shoes with tan leather-and-mesh uppers, cushioned EVA midsoles, and grippy Vibram® rubber outsoles.
(0)
$150 $150
SALE
$150 $150
SALE
Men's Access Hiking Shoes, Waterproof
L.L.Bean Men's Access Hiking Shoes, Waterproof
A gray waterproof hiking shoe with nubuck leather, cushioned support, and grippy rubber traction for trails.
(0)
$140 $140
SALE
$140 $140
SALE
Men's On Cloudvista Trail Running Shoes
On Men's On Cloudvista Trail Running Shoes
Gray trail running shoes with lightweight mesh uppers, responsive cushioning, rocker geometry and sticky rubber traction.
(0)
$150 $150
SALE
$150 $150
SALE
Men's Keen Targhee IV Waterproof Hiking Shoes
Keen Men's Keen Targhee IV Waterproof Hiking Shoes
A waterproof leather hiking shoe with breathable mesh, supportive cushioning, and multi-directional traction.
(0)
$170 $170
SALE
$170 $170
SALE
Men's Oboz Sawtooth X B-DRY Hikers, Low
Oboz Men's Oboz Sawtooth X B-DRY Hikers, Low
A brown waterproof hiking shoe with nubuck leather, breathable lining, supportive nylon shank and mud-shedding traction.
(0)
$185 $185
SALE
$185 $185
SALE
Men's Trail Model X Ventilated Hiking Shoes
L.L.Bean Men's Trail Model X Ventilated Hiking Shoes
A brown suede-and-rubber hiking shoe with breathable mesh, water resistance, protective toe and enhanced wet traction.
(0)
$99.95 $69.99
SALE
$99.95 $69.99
SALE
Men's Heritage Hiking Shoes, Waterproof
L.L.Bean Men's Heritage Hiking Shoes, Waterproof
Waterproof tan hiking shoes with suede-and-nylon uppers, cushioned insoles, and grippy rubber outsoles for trail traction.
(0)
$140 $94.99
SALE
$140 $94.99
SALE
Men's On Cloudsurfer Trail 2 Running Shoes
On Men's On Cloudsurfer Trail 2 Running Shoes
A gray trail running shoe with cushioned Helion foam and a grippy Missiongrip rubber outsole.
(0)
$170 $170
SALE
$170 $170
SALE
Men's On Cloudvista 3 Trail Running Shoes
On Men's On Cloudvista 3 Trail Running Shoes
A white trail running shoe with breathable construction, responsive Speedboard®, Helion™ cushioning, and grippy Missiongrip™ traction.
(0)
$160 $160
SALE
$160 $160
SALE
Men's Trail Model X Waterproof Hiking Shoes
L.L.Bean Men's Trail Model X Waterproof Hiking Shoes
A gray suede hiking shoe with a waterproof membrane, rock plate, and high-traction rubber outsole.
(0)
$110 $110
SALE
$110 $110
SALE
Men's HOKA Challenger 8 Trail Shoes, GORE-TEX
HOKA Men's HOKA Challenger 8 Trail Shoes, GORE-TEX
Black road-to-trail running shoes with a waterproof GORE-TEX membrane, EVA midsole and 4mm multi-directional lugs.
(0)
$165 $165
SALE
$165 $165
SALE
Men's Elevation Trail Shoes, Waterproof
L.L.Bean Men's Elevation Trail Shoes, Waterproof
Waterproof blue trail shoes with recycled mesh, rock protection, cushioned midsoles, and grippy rubber outsoles.
(0)
$130 $130
SALE
$130 $130
SALE
Men's HOKA Challenger 8 Trail Shoes
HOKA Men's HOKA Challenger 8 Trail Shoes
Men’s blue trail running shoes with cushioned EVA midsoles, recycled mesh uppers and grippy 4mm lugs.
(0)
$150 $150
SALE
$150 $150
SALE
Men's Trail Model X Waterproof Hiking Shoes, Leather
L.L.Bean Men's Trail Model X Waterproof Hiking Shoes, Leather
Brown waterproof leather hiking shoes with breathable mesh, EVA cushioning, rock plate, and high-traction rubber outsoles.
(0)
$120 $120
SALE
$120 $120
SALE
Men's Oboz Sawtooth X B-DRY Hikers, Mid
Oboz Men's Oboz Sawtooth X B-DRY Hikers, Mid
A gray waterproof hiking boot with breathable nubuck leather, cushioned support and multidirectional lugs for traction.
(93)
$200 $200
SALE
What customers like:
Great support
High comfort
Excellent fitting
Superior quality
$200 $200
SALE
Men's HOKA Transport 2 Shoes
HOKA Men's HOKA Transport 2 Shoes
A gray polyester city-to-trail shoe with recycled materials, water repellency, quick-toggle laces and 360-degree reflectivity.
(0)
$155 $155
SALE
$155 $155
SALE
Men's Oboz Bridger Mid B-Dry Hiking Boots
Oboz Men's Oboz Bridger Mid B-Dry Hiking Boots
A brown leather hiking boot with waterproof breathable protection, cushioned arch support and grippy granite-peak tread.
(181)
$220 $220
SALE
What customers like:
Light
Sturdy
Comfortable
Good quality orthotic base
Looks great
$220 $220
SALE
Men's Elevation Travel Slip-On Shoes, Waterproof
L.L.Bean Men's Elevation Travel Slip-On Shoes, Waterproof
A green waterproof slip-on shoe with breathable recycled mesh, cushioned support, and grippy rubber traction.
(0)
$130 $130
SALE
$130 $130
SALE
Men's Cresta II Waterproof Hiking Boots, Leather
L.L.Bean Men's Cresta II Waterproof Hiking Boots, Leather
A brown waterproof leather hiking boot with TEK2.5 membrane and Vibram rubber sole for trail traction.
(0)
$280 $280
SALE
$280 $280
SALE
Men's Heritage Hiking Boots, Waterproof
L.L.Bean Men's Heritage Hiking Boots, Waterproof
Waterproof gray hiking boots with suede-and-nylon uppers, cushioned insoles, and grippy rubber outsoles for trail traction.
(0)
$150 $99.99
SALE
$150 $99.99
SALE
Men's Keen Targhee IV Mid Waterproof Hiking Boots
Keen Men's Keen Targhee IV Mid Waterproof Hiking Boots
A waterproof mid hiking boot with nubuck leather, breathable mesh, supportive cushioning, and grippy multi-directional lugs.
(0)
$180 $180
SALE
$180 $180
SALE
Men's Trail Model X Waterproof Hiking Boots, Leather
L.L.Bean Men's Trail Model X Waterproof Hiking Boots, Leather
A waterproof brown leather hiking boot with rubberized toe protection and grippy rubber outsoles for trails.
(0)
$130 $130
SALE
$130 $130
SALE
Men's Access Hiking Boots, Waterproof
L.L.Bean Men's Access Hiking Boots, Waterproof
A waterproof gray hiking boot with nubuck leather, recycled mesh, grippy traction and cushioned all-day comfort.
(0)
$150 $150
SALE
$150 $150
SALE

Men's Trail Shoes

Men’s trail shoes belong to a familiar part of time outside: choosing a trail, making a plan and finding a pair that feels right for the person wearing it. That plan might be a regular visit to a favorite local trail, a chance to explore somewhere unfamiliar with a friend or a family outing with plenty of stops along the way. The starting point is personal preference, not someone else’s idea of the perfect shoe. Some men prefer an understated appearance; others look for a more distinctive shape or details that reflect their individual style. Looking closely at the profile, overall design and product description helps put those preferences into focus. A photograph offers a first impression, while the accompanying information provides the details needed for a more thoughtful comparison. Two pairs that look similar may have different sizing guidance, materials or care requirements, so appearance is only one part of the decision. It also helps to separate a preferred look from the practical details that matter most to the wearer. Someone replacing a familiar pair may already know which aspects of its shape and fit they want to find again. Someone choosing trail shoes for the first time may begin with fewer preferences and give each option a closer look. For those interested in that particular style, men’s slip-on trail shoes offer another direction to explore. The choice remains individual: consider the design, read the details and keep the intended trail plans in mind. A useful comparison starts with what matters to the wearer rather than a long list of unfamiliar terms. That might mean prioritizing a familiar silhouette, taking extra time with sizing information or narrowing the selection to designs that suit a personal sense of style. There is room for different preferences without treating any single look as the answer for everyone.

Fit deserves particular attention when comparing men’s trail shoes, because a size label is a starting point rather than a complete description. Length, width and the shape of the foot all contribute to how a pair feels. A man who knows his usual shoe size can still benefit from reviewing the sizing information for the pair under consideration, especially when replacing a style worn for years. If measurements are needed, follow the directions supplied with the size chart and consider both feet rather than assuming they are identical. Trying shoes with the socks intended for the trail also makes the comparison more relevant. Notice where the toes sit, how the heel feels and whether any part of the shoe presses against the foot. There should be no need to dismiss an uncomfortable spot simply because the stated size seems correct. A quiet try-on at home can reveal details that are easy to miss when attention is on the appearance alone. Stand in both shoes, take a few ordinary steps and pay attention to each foot separately. The useful question is how that particular pair fits, not whether its number matches every other pair in the closet. Materials and construction deserve the same individual attention. Read what is listed for each pair instead of assuming that a certain appearance indicates a particular material or that similar-looking shoes are made alike. Where measurements or fit notes are provided, use those specifics to compare options. Personal experience can help here, too: remembering where a previous pair felt too narrow, too loose or simply unfamiliar gives the next choice a clearer starting point. These observations do not require a technical vocabulary. A straightforward description of what feels right—and what does not—is often more useful than choosing by appearance or size alone. The aim is a considered choice based on the wearer’s own feet, preferences and trail plans.

Care and durability are worth considering before making a selection, particularly for someone who wants a pair to remain part of a regular trail routine. Start with the care directions for the shoes themselves. Cleaning and drying methods should follow those directions rather than a general rule borrowed from another pair, and any treatment should be appropriate for the stated materials. Before reaching for a cleaning product, check the instructions instead of relying on the shoe’s appearance to judge what it needs. This is a useful consideration for anyone who prefers a simple care routine: understanding the upkeep in advance makes it easier to decide whether a pair suits those preferences. Construction details also provide a more concrete basis for comparison than appearance alone. A substantial-looking shoe and a streamlined-looking shoe should each be considered on their own descriptions, without assuming that one particular shape establishes how long either will last. Over time, paying attention to changes in fit, visible wear and the condition of the shoes helps keep the decision grounded in the pair actually being worn. The same thoughtful approach applies when choosing men’s trail shoes as a gift. A friend, partner or family member who enjoys spending time on trails may appreciate a gift that reflects that interest, but footwear is personal enough to reward a little preparation. Knowing the recipient’s usual size helps; knowing the fit and styling preferences they already favor helps more. A conversation about what they like in their present shoes can offer better direction than guessing from a photograph. For a surprise, stay close to preferences that are already familiar rather than choosing an entirely different look simply for novelty. Whether the purchase is a gift, a replacement or a first pair, the most useful details are the ones that connect the shoes to the person who will wear them. Thoughtful selection leaves room for individual taste while giving fit, care and product information the attention they deserve.

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