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Sport Trail Shoes

Find sport trail shoes that suit your fit preferences and trail plans. Browse the available styles, then compare sizing information and individual product details to understand how each pair differs before making your choice.

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Men's Elevation Trail Shoes, Waterproof
L.L.Bean Men's Elevation Trail Shoes, Waterproof
A lightweight blue trail shoe with waterproof mesh upper, thermoregulating lining, and grippy rubber outsole.
(0)
$130 $130
SALE
$130 $130
SALE
Men's Oboz Sawtooth X B-DRY Hikers, Low
Oboz Men's Oboz Sawtooth X B-DRY Hikers, Low
A rugged brown trail shoe with waterproof nubuck leather, breathable lining, and multi-directional traction lugs.
(0)
$165 $165
SALE
$165 $165
SALE
Men's Elevation H2O Shoes
L.L.Bean Men's Elevation H2O Shoes
A lightweight green water shoe with breathable nylon/neoprene, quick-drying design, and VertiGrip wet/dry traction.
(0)
$99.95 $64.99
SALE
$99.95 $64.99
SALE
Men's Trail Model X Waterproof Hiking Shoes, Leather
L.L.Bean Men's Trail Model X Waterproof Hiking Shoes, Leather
A brown waterproof leather hiking shoe with enhanced traction, breathable mesh panels, and recycled polyester laces.
(0)
$120 $120
SALE
$120 $120
SALE
Men's Trail Model X Waterproof Hiking Shoes
L.L.Bean Men's Trail Model X Waterproof Hiking Shoes
A brown suede leather hiking shoe with waterproof protection and enhanced traction for wet surfaces.
(0)
$110 $110
SALE
$110 $110
SALE
Men's On Cloudvista Trail Running Shoes
On Men's On Cloudvista Trail Running Shoes
A lightweight gray trail running shoe with breathable recycled mesh, Helion™ superfoam cushioning, and Missiongrip™ rubber traction.
(0)
$150 $150
SALE
$150 $150
SALE
Men's 1985 Mountain Classic Sneakers
L.L.Bean Men's 1985 Mountain Classic Sneakers
A versatile gray sneaker featuring water-resistant suede, recycled mesh, and grippy VertiGrip rubber outsole for outdoor adventures.
(0)
$110 $79.99
SALE
$110 $79.99
SALE
Men's On Cloudsurfer Trail 2 Running Shoes
On Men's On Cloudsurfer Trail 2 Running Shoes
A lightweight gray trail running shoe featuring a cushioned Helion™ midsole and durable Missiongrip™ rubber outsole.
(0)
$170 $170
SALE
$170 $170
SALE
Men's HOKA Challenger 8 Trail Shoes, GORE-TEX
HOKA Men's HOKA Challenger 8 Trail Shoes, GORE-TEX
A black trail running shoe with GORE-TEX waterproofing, EVA midsole, and 4mm lugs for all-terrain traction.
(0)
$165 $165
SALE
$165 $165
SALE
Men's Trail Model X Ventilated Hiking Shoes
L.L.Bean Men's Trail Model X Ventilated Hiking Shoes
A water-resistant suede hiking shoe with enhanced traction, comfort, and recycled materials for outdoor adventures.
(0)
$99.95 $84.99
SALE
$99.95 $84.99
SALE
Men's HOKA Transport 2 Shoes
HOKA Men's HOKA Transport 2 Shoes
A versatile gray athleisure shoe featuring recycled polyester, water-repellent treatment, and a Vibram EcoStep outsole.
(0)
$150 $150
SALE
$150 $150
SALE
Men's Access Hiking Shoes, Waterproof
L.L.Bean Men's Access Hiking Shoes, Waterproof
A waterproof hiking shoe in carbon navy with leather/rubber upper and EVA midsole for all-day comfort.
(0)
$140 $119.99
SALE
$140 $119.99
SALE
Men's NextVenture Hiking Shoes, Waterproof
L.L.Bean Men's NextVenture Hiking Shoes, Waterproof
A waterproof tan hiking shoe with cushioned EVA midsole, Vibram® outsole, and breathable mixed-material upper.
(0)
$150 $150
SALE
$150 $150
SALE
Men's HOKA Challenger 8 Trail Shoes
HOKA Men's HOKA Challenger 8 Trail Shoes
A blue trail running shoe featuring a lightweight mesh upper, cushioned EVA midsole, and grippy 4mm lugs.
(0)
$150 $150
SALE
$150 $150
SALE
Men's Bean's Comfort Fitness Walking Shoes, Waterproof
L.L.Bean Men's Bean's Comfort Fitness Walking Shoes, Waterproof
A weatherproof, cushioned walking shoe with a breathable polyester mesh upper and durable VertiGrip rubber outsole.
(543)
$120 $99.99
SALE
What customers like:
Fit
Quality
Comfort
Durability
Arch support
$120 $99.99
SALE
Men's Oboz Bridger Low B-Dry Hiking Shoes
Oboz Men's Oboz Bridger Low B-Dry Hiking Shoes
A versatile dark shadow hiking shoe with waterproof nubuck leather and advanced cushioning for all activities.
(279)
$160 $160
SALE
What customers like:
Durable construction
High-quality materials
Excellent support
Comfortable fit
Professional customer service
$160 $160
SALE
Women's Oboz Sawtooth X B-DRY Hikers, Low
Oboz Women's Oboz Sawtooth X B-DRY Hikers, Low
A rugged, waterproof trail shoe with durable nubuck leather and reliable traction, perfect for muddy trails.
(158)
$165 $165
SALE
$165 $165
SALE
Men's Oboz Sawtooth X B-DRY Hikers, Mid
Oboz Men's Oboz Sawtooth X B-DRY Hikers, Mid
A rugged, waterproof hiker with a nubuck leather upper and reliable traction, perfect for muddy trails.
(93)
$180 $180
SALE
What customers like:
Durable quality
Great support
High comfort
Excellent fitting
Reliable traction
$180 $180
SALE
Women's Elevation Trail Shoes, Waterproof
L.L.Bean Women's Elevation Trail Shoes, Waterproof
A lightweight green trail shoe with waterproof mesh, durable rubber outsole, and thermoregulating lining for comfort.
(0)
$130 $130
SALE
$130 $130
SALE
Men's Elevation Travel Slip-On Shoes, Waterproof
L.L.Bean Men's Elevation Travel Slip-On Shoes, Waterproof
A lightweight green mesh and rubber travel shoe with waterproof protection, breathable comfort, and grippy traction.
(0)
$130 $130
SALE
$130 $130
SALE
Women's HOKA Challenger 8 Trail Shoes, GORE-TEX
HOKA Women's HOKA Challenger 8 Trail Shoes, GORE-TEX
A gray trail running shoe with GORE-TEX membrane, EVA midsole, and 100% recycled mesh upper.
(0)
$165 $165
SALE
$165 $165
SALE
Women's NextVenture Hiking Shoes, Waterproof
L.L.Bean Women's NextVenture Hiking Shoes, Waterproof
A waterproof blue hiking shoe with mesh, rubber, and leather for comfort, breathability, and reliable traction.
(0)
$150 $150
SALE
$150 $150
SALE
Men's On Cloud 6 Shoes
On Men's On Cloud 6 Shoes
A lightweight blue sneaker with a recycled mesh upper, cushioned CloudTec® midsole, and durable rubber outsole.
(0)
$150 $150
SALE
$150 $150
SALE
Men's Trail Model X Waterproof Hiking Boots, Leather
L.L.Bean Men's Trail Model X Waterproof Hiking Boots, Leather
A brown waterproof leather hiking boot with enhanced traction, recycled polyester laces, and breathable mesh panels.
(0)
$130 $130
SALE
$130 $130
SALE

Sport Trail Shoes

Sport Trail Shoes bring an outdoorsy point of view to a footwear collection, with styles that range from understated to distinctly sporty. When narrowing down your favorites, start with what you genuinely like to wear: simple shapes and subtle colors, contrasting accents, or a more pronounced athletic look. Picture the shoes beside the pants and layers already in your closet rather than considering them in isolation. A pair that feels like your style is often a more satisfying choice than one chosen for appearance alone in a single photograph. Look through the available views, compare the shape of the toe and the overall profile, and notice which details keep drawing your eye. Small differences can make two otherwise similar pairs feel quite different to you.

Choosing among Sport Trail Shoes also calls for a little attention to sizing and personal preference. Use your usual shoe size as a starting point, then check the sizing information for each pair rather than assuming every style will fit the same way. If you know your preferred width, keep that in mind as you compare the available options. Think about what you appreciate in shoes you already own—and what you would change. Perhaps one pair feels crowded at the toes, while another never seems quite right around the heel. Those everyday observations give you something concrete to work with when reading individual descriptions and fit notes. Before making your selection, review the details for that particular pair; a shared category name does not mean every shoe has the same construction or intended purpose.

For someone who enjoys choosing their own way along a trail, a thoughtfully selected pair of shoes can make a personal gift. The best starting point is familiarity with the recipient’s preferences, not a guess about what they ought to like. Notice whether they favor quiet colors or brighter accents, and confirm both their size and any width preference before ordering. If they are particular about footwear, choosing together can be part of the pleasure: a few favorites pulled up side by side, an honest opinion about the colors, and time to look over the details. Whether you are shopping for yourself or someone close to you, let individual fit information, personal style and the stated purpose of each pair shape your decision. The aim is a considered choice that feels right for the person wearing it.

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