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Comfortable Trail Shoes

Find comfortable trail shoes for your time outdoors, with styles to suit different preferences. Compare each pair’s fit information, sizing guidance and product details to narrow your options and choose the trail footwear that’s right for you.

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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 Bucksport Shoes, Plain Toe
L.L.Bean Men's Bucksport Shoes, Plain Toe
A rugged, waterproof brown leather shoe with Vibram® rubber outsoles and anti-odor technology for all-day comfort.
(835)
$170 $170
SALE
What customers like:
Perfect fit
Quality
Durability
Excellent value
Comfortable
$170 $170
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 lightweight, waterproof hiking shoe with advanced cushioning, superior arch support, and a durable rubber toe cap.
(279)
$160 $160
SALE
What customers like:
Durable design
Excellent sole
High-quality construction
Superior arch support
Comfortable fit
$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 trail shoe with waterproof nubuck leather and reliable traction for wet, muddy conditions.
(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 rugged brown hiker with waterproof B-DRY lining, nubuck leather upper, and reliable multi-directional traction.
(100)
$180 $180
SALE
What customers like:
Snug ankle support
Waterproof protection
Warm and insulated
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 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 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 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 NextVenture Hiking Shoes, Waterproof
L.L.Bean Men's NextVenture Hiking Shoes, Waterproof
A tan waterproof hiking shoe with leather and rubber materials, cushioned EVA midsole, and Vibram outsole.
(0)
$150 $150
SALE
$150 $150
SALE
Men's Trail Model X Waterproof Hiking Boots
L.L.Bean Men's Trail Model X Waterproof Hiking Boots
A brown suede leather hiking boot with waterproof features and enhanced traction for wet conditions.
(0)
$120 $120
SALE
$120 $120
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
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 On Cloudrunner 3 Running Shoes
On Men's On Cloudrunner 3 Running Shoes
A cushioned, multi-color running shoe with breathable mesh upper, Helion™ superfoam midsole, and durable rubber outsole.
(0)
$150 $150
SALE
$150 $150
SALE
Women's Oboz Ousel B-Dry Hiking Shoes
Oboz Women's Oboz Ousel B-Dry Hiking Shoes
A waterproof hiking shoe with leather upper, rubber outsole, and recycled polyester laces for superior comfort.
(0)
$145 $145
SALE
$145 $145
SALE
Men's Heritage Hiking Boots, Waterproof
L.L.Bean Men's Heritage Hiking Boots, Waterproof
A waterproof gray hiking boot with suede-and-nylon upper, grippy rubber outsole, and cushioned comfort insole.
(0)
$150 $109.99
SALE
$150 $109.99
SALE
Men's Elevation Travel Slip-On Shoes, Waterproof
L.L.Bean Men's Elevation Travel Slip-On Shoes, Waterproof
A lightweight green travel shoe with waterproof mesh, grippy rubber outsole, and thermoregulating lining for comfort.
(0)
$130 $130
SALE
$130 $130
SALE
Women's Trail Model X Waterproof Hiking Shoes
L.L.Bean Women's Trail Model X Waterproof Hiking Shoes
A gray suede and rubber hiking shoe featuring waterproof protection, breathable mesh panels, and enhanced wet-surface traction.
(0)
$110 $110
SALE
$110 $110
SALE
Men's Elevation H2O Shoes
L.L.Bean Men's Elevation H2O Shoes
A lightweight gray water-friendly shoe with nylon and neoprene, offering quick-drying comfort and wet/dry traction.
(0)
$99.95 $64.99
SALE
$99.95 $64.99
SALE
Men's New Balance 574V3 Walking Shoes
New Balance Men's New Balance 574V3 Walking Shoes
A versatile walking shoe with a breathable suede-and-mesh upper and durable rubber outsole for all-day comfort.
(0)
$89.99 $89.99
SALE
$89.99 $89.99
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
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 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 Cresta II Waterproof Hiking Boots, Leather
L.L.Bean Men's Cresta II Waterproof Hiking Boots, Leather
A rugged brown leather hiking boot with waterproof membrane and Vibram® sole for reliable traction and comfort.
(0)
$280 $280
SALE
$280 $280
SALE

Comfortable Trail Shoes

Comfortable Trail Shoes belong among the essentials that make getting outside feel inviting, whether a familiar trail is part of your weekly routine or you’re looking forward to exploring somewhere new with friends. Choosing a pair starts with your own sense of comfort: the shape that feels right on your feet, the fit you prefer and the styles you’ll be glad to reach for again. Think about shoes you’ve enjoyed wearing in the past and what made them favorites. Perhaps they gave your toes enough room, felt secure around your heels or came in a size that never left you wishing for a little more space. Those details are useful starting points when comparing options. A familiar size alone doesn’t tell the whole story, so take a moment to check each pair’s sizing information and any fit notes before making your choice. The goal is a pair that feels like your choice—not simply the one someone else prefers.

Comfort is personal, and it’s worth giving the small details some attention. When trying on trail shoes, wear the socks you expect to wear with them and check the fit on both feet. Give your toes room to move, notice whether your heel shifts as you walk and pay attention to any pressure across the top or sides of your foot. If something feels cramped or awkward, compare another size or shape rather than assuming it will become comfortable later. Consider how you like your shoes to look, too. Understated colors can feel familiar and easy to coordinate, while a brighter accent may be more your style. Neither approach is more suited to enjoying a trail lined with ferns or pausing with friends where the trees open up to a view. What matters is choosing thoughtfully, with your preferences at the center of the decision.

Trail shoes can also make a thoughtful gift for someone who enjoys time outside, from a partner with a favorite local loop to a friend who’s always suggesting another shared outing. Footwear is a personal choice, though, so a little groundwork helps. Knowing the recipient’s usual size is useful; knowing their preferred width, fit and style is even better. If you’re unsure, letting them help choose can be part of the gift rather than spoiling the surprise. For your own next pair, use the same care: compare the individual descriptions, look closely at sizing details and give yourself permission to favor what feels familiar. There’s something special about an unhurried afternoon outdoors—the conversation, the turn in the path, the chance to spend a little longer together. Choosing comfortable trail shoes is a practical place to begin.

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