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Cushioned Trail Shoes

Find cushioned trail shoes that suit your fit and style preferences. Compare available styles and sizes, then check each pair’s product details for cushioning information and fit guidance to help narrow your choices.

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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 Oboz Bridger Low B-Dry Hiking Shoes
Oboz Men's Oboz Bridger Low B-Dry Hiking Shoes
A versatile, waterproof hiking shoe with advanced cushioning, superior arch support, and a durable granite peak outsole.
(279)
$160 $160
SALE
What customers like:
Durable construction
High-quality materials
Superior arch 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 gray hiking shoe with waterproof nubuck leather and reliable traction for wet, muddy trails.
(158)
$165 $165
SALE
$165 $165
SALE
Women's Oboz Sawtooth X B-DRY Hikers, Mid
Oboz Women's Oboz Sawtooth X B-DRY Hikers, Mid
A waterproof brown hiker with nubuck leather, rubber, and nylon for comfort, support, and reliable traction.
(100)
$180 $180
SALE
What customers like:
Warmth
Snug ankle support
Sturdy construction
Comfortable fit
$180 $180
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 reliable traction and breathable nubuck leather upper for muddy trails.
(93)
$180 $180
SALE
What customers like:
Great fitting
Excellent support
High comfort
Superior quality
$180 $180
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, cushioned EVA midsole, and durable mesh upper.
(0)
$165 $165
SALE
$165 $165
SALE
Men's Trail Model X Waterproof Hiking Shoes, Camo
L.L.Bean Men's Trail Model X Waterproof Hiking Shoes, Camo
A waterproof hiking shoe featuring water-resistant suede, breathable mesh panels, and enhanced traction for wet trails.
(0)
$110 $92.99
SALE
$110 $92.99
SALE
Men's HOKA Gaviota 6 Running Shoes
HOKA Men's HOKA Gaviota 6 Running Shoes
A blue running shoe with breathable mesh, exceptional cushioning, and enhanced support for daily miles.
(0)
$175 $175
SALE
$175 $175
SALE
Men's 1985 Mountain Classic Sneakers
L.L.Bean Men's 1985 Mountain Classic Sneakers
A gray sneaker featuring water-resistant suede, recycled nylon, and a grippy VertiGrip rubber outsole for traction.
(0)
$110 $79.99
SALE
$110 $79.99
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 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 HOKA Challenger 8 Trail Shoes
HOKA Men's HOKA Challenger 8 Trail Shoes
A lightweight blue trail running shoe featuring a recycled mesh upper, cushioned EVA midsole, and grippy outsole.
(0)
$150 $150
SALE
$150 $150
SALE
Men's NextVenture Hiking Shoes, Waterproof
L.L.Bean Men's NextVenture Hiking Shoes, Waterproof
A tan waterproof hiking shoe with a cushioned EVA midsole, Vibram outsole, and breathable TEK2.5 membrane.
(0)
$150 $150
SALE
$150 $150
SALE
Men's Trail Model X Waterproof Hiking Shoes
L.L.Bean Men's Trail Model X Waterproof Hiking Shoes
A gray suede and rubber hiking shoe with waterproof protection, breathable mesh panels, and enhanced wet-surface traction.
(0)
$110 $110
SALE
$110 $110
SALE
Men's Access Hiking Shoes, Waterproof
L.L.Bean Men's Access Hiking Shoes, Waterproof
A waterproof gray hiking shoe featuring recycled mesh, nubuck leather, and grippy rubber for all-day comfort.
(0)
$140 $140
SALE
$140 $140
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 Oboz Sawtooth X B-DRY Hikers, Low
Oboz Men's Oboz Sawtooth X B-DRY Hikers, Low
A rugged brown trail shoe with waterproof B-DRY lining, nubuck leather upper, and reliable multi-directional traction.
(0)
$165 $165
SALE
$165 $165
SALE
Men's Storm Chaser 5 Slip-Ons
L.L.Bean Men's Storm Chaser 5 Slip-Ons
A tough, waterproof slip-on with leather upper and rubber outsole, ideal for cold, wet conditions.
(3,695)
$130 $130
SALE
What customers like:
High quality
Easy to slip on
Versatile
Comfortable
Warm
$130 $130
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 $120
SALE
What customers like:
Fit
Quality
Comfort
Durability
Arch support
$120 $120
SALE
Women's Trail Model X Waterproof Hiking Shoes, Leather
L.L.Bean Women's Trail Model X Waterproof Hiking Shoes, Leather
A brown waterproof leather hiking shoe with recycled laces, enhanced traction, and thermoregulating comfort lining.
(0)
$120 $120
SALE
$120 $120
SALE
Men's Keen Targhee IV Waterproof Hiking Shoes
Keen Men's Keen Targhee IV Waterproof Hiking Shoes
A waterproof leather hiking shoe offering stability, support, and comfort with eco-friendly features and durable traction.
(0)
$170 $170
SALE
$170 $170
SALE
Women's Keen Targhee IV Waterproof Hiking Shoes
Keen Women's Keen Targhee IV Waterproof Hiking Shoes
A waterproof leather hiking shoe with recycled laces, Eco Anti-Odor, and durable traction for all-terrain adventures.
(0)
$170 $170
SALE
$170 $170
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 featuring waterproof protection, breathable recycled upper, and grippy outsole.
(0)
$130 $130
SALE
$130 $130
SALE
Women's Trail Model X Ventilated Hiking Shoes
L.L.Bean Women's Trail Model X Ventilated Hiking Shoes
A purple suede hiking shoe with water-resistant features and enhanced traction for wet surfaces.
(0)
$99.95 $99.95
SALE
$99.95 $99.95
SALE

Cushioned Trail Shoes

Cushioned Trail Shoes bring together two things worth considering as you choose your next pair: the feel you prefer underfoot and a style made for the trail. Cushioning is a personal preference, and more isn’t automatically better for every person. Some people enjoy a noticeably cushioned feel, while others prefer something less pronounced. Think about what you like in the shoes you already own, including where they feel roomy, where they feel snug, and what you would change. Those familiar details make a useful starting point when comparing options. Whether your favorite trail winds through a neighborhood woodland or leads to a spot you visit with family every fall, choosing shoes begins with your own preferences—not someone else’s idea of the perfect pair.

Fit deserves just as much attention as cushioning. As you browse, compare the available sizes and widths, check each pair’s fit notes, and use the size chart rather than relying on size alone. Leave room for your toes to move without choosing a fit that lets your foot slide around, and pay attention to how the heel and midfoot feel. When trying shoes on, wear the socks you expect to wear with them and take time to notice any pressure points. A pair that looks right on the screen still needs to feel right on your feet. If you’re deciding between two options, details such as the shape of the toe area, the way the shoes fasten, and your preferred amount of cushioning can help narrow the choice. Color and overall style matter, too; there’s nothing wrong with choosing a pair you enjoy looking at once the fit feels right.

For someone who looks forward to time on the trail, cushioned trail shoes can also make a thoughtful gift—especially when you know their size, preferred fit, and taste. Picture the family member who always suggests the wooded loop after a weekend get-together, or the friend who stops to point out the first turning leaves. Their enthusiasm gives the gift meaning, but their footwear preferences should guide the selection. If you’re unsure, choosing together can be part of the experience, with a shared trail outing to look forward to afterward. This collection offers a place to compare options at your own pace, keeping the decision centered on the details that matter to the person wearing them. Start with fit, consider the cushioning you prefer, and choose a style that feels like your own.

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