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Outdoor Trail Shoes

Explore outdoor trail shoes and find a style that suits your plans. Compare the available options, then check each pair’s product details for sizing, fit guidance and intended terrain to help narrow your choice.

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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
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 for muddy trails.
(93)
$180 $180
SALE
What customers like:
Great support
High comfort
Excellent fitting
Superior quality
$180 $180
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, TEK2.5® membrane, and enhanced traction for wet trails.
(0)
$110 $92.99
SALE
$110 $92.99
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 eco-friendly materials for outdoor adventures.
(0)
$99.95 $99.95
SALE
$99.95 $99.95
SALE
Men's Heritage Hiking Shoes, Waterproof
L.L.Bean Men's Heritage Hiking Shoes, Waterproof
A waterproof tan hiking shoe with a suede-and-nylon upper and grippy rubber outsole for tough trails.
(0)
$140 $99.99
SALE
$140 $99.99
SALE
Women's Access Hiking Shoes, Waterproof
L.L.Bean Women's Access Hiking Shoes, Waterproof
A waterproof hiking shoe with a recycled polyester mesh and nubuck leather upper for all-day comfort.
(0)
$140 $140
SALE
$140 $140
SALE
Men's Elevation H2O Shoes
L.L.Bean Men's Elevation H2O Shoes
A lightweight gray water-friendly shoe with breathable nylon/neoprene, convertible heel, and VertiGrip outsole for traction.
(0)
$99.95 $64.99
SALE
$99.95 $64.99
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 NextVenture Waterproof Slip-On Shoes, Leather
L.L.Bean Men's NextVenture Waterproof Slip-On Shoes, Leather
A tan leather slip-on shoe with waterproof protection, cushioned comfort, and a grippy Vibram rubber outsole.
(0)
$150 $150
SALE
$150 $150
SALE
Men's HOKA Challenger 8 Trail Shoes
HOKA Men's HOKA Challenger 8 Trail Shoes
A lightweight blue trail running shoe with cushioned EVA midsole and durable, recycled mesh upper.
(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 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 details.
(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 gray suede hiking shoe with waterproof membrane, breathable mesh panels, and enhanced rubber outsole traction.
(0)
$110 $110
SALE
$110 $110
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 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 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
Men's On Cloudvista Trail Running Shoes
On Men's On Cloudvista Trail Running Shoes
A lightweight gray trail running shoe featuring breathable mesh, Helion™ superfoam cushioning, and Missiongrip™ rubber traction.
(0)
$150 $150
SALE
$150 $150
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 NextVenture Hiking Shoes, Waterproof
L.L.Bean Men's NextVenture Hiking Shoes, Waterproof
A waterproof tan hiking shoe with a cushioned EVA midsole, Vibram outsole, and breathable mixed-material upper.
(0)
$150 $150
SALE
$150 $150
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 Storm Chaser 5 Slip-Ons
L.L.Bean Men's Storm Chaser 5 Slip-Ons
A durable, waterproof slip-on with leather upper, rubber outsole, and exceptional cushioning for all-weather comfort.
(3,695)
$130 $130
SALE
What customers like:
High quality
Warm and cozy
Versatile design
Easy to slip on
Comfortable fit
$130 $130
SALE
Men's Oboz Bridger Mid B-Dry Hiking Boots
Oboz Men's Oboz Bridger Mid B-Dry Hiking Boots
A waterproof, breathable hiking boot with a leather upper and rubber sole, ideal for tricky trails.
(181)
$200 $200
SALE
What customers like:
Light
Sturdy
Comfortable
Good quality orthotic base
Looks great
$200 $200
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 upper, breathable lining, and rugged traction for wet, muddy trails.
(100)
$180 $180
SALE
What customers like:
Warm for cold conditions
Snug ankle support
Sturdy construction
Comfortable fit
$180 $180
SALE

Outdoor Trail Shoes

Outdoor Trail Shoes are part of the anticipation of heading outside: choosing a route, inviting a friend and setting aside a little time to see where the path leads. Whether you’re drawn to a familiar loop through the woods or a trail you’ve been meaning to explore, choosing a pair starts with your own preferences rather than someone else’s checklist. Think about the shoes you already enjoy wearing, the styles you reach for most often and what you’d like to fit differently. A favorite pair can be a useful point of comparison, especially when you know its size and shape. Explore the selection with those details in mind, looking for a balance of personal style, fit and the qualities that matter to you.

Fit deserves a closer look than the size printed on the box. Read the sizing information for each pair, including any notes about width or whether to order a different size than usual. When trying shoes on, wear the socks you expect to wear with them, check both feet and take time to walk around indoors. Notice whether your toes have room, whether your heel moves more than you’d like and whether any part of the shoe presses against your foot. Comparing those impressions with a familiar pair can make the decision feel less like guesswork. Product descriptions and care instructions are also worth reading before choosing; details vary from one style to another, and a similar appearance doesn’t necessarily mean a similar fit. Color and design can help narrow the options, but neither should outweigh how a pair feels on your feet.

Trail shoes can be a thoughtful gift for someone who looks forward to time outside—the friend who always suggests a woodland walk or the family member who turns a free morning into an invitation to explore. Footwear is personal, though, so a little knowledge goes a long way. Start with the recipient’s current size, preferred width and everyday style, and leave room for them to make the final choice when possible. An understated color may suit someone who likes a simple look, while a more distinctive combination might feel right for someone whose outdoor wardrobe is full of color. For yourself or someone close to you, the most meaningful choice is one that reflects the person, not just the occasion. There’s something worth looking forward to in a trail branching through the trees, a companion beside you and an afternoon with no need to rush.

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