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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 brown leather-and-rubber slip-on with waterproof protection, insulated cushioning, and siped traction for snow and slush.
(3,695)
$130 $130
SALE
$130 $130
SALE
Men's Bucksport Shoes, Plain Toe
L.L.Bean Men's Bucksport Shoes, Plain Toe
A brown waterproof oiled-leather shoe with Goodyear welted construction, Vibram® lugged traction, and all-day comfort.
(835)
$170 $170
SALE
What customers like:
Perfect fit
Quality
Durability
Excellent value
Comfortable
$170 $170
SALE
Women's Snow Sneaker 5 Shoes, Lace-Up
L.L.Bean Women's Snow Sneaker 5 Shoes, Lace-Up
A warm waterproof suede-and-fabric winter sneaker with 200-gram insulation and rugged rubber traction for snow.
(782)
$140 $140
SALE
What customers like:
Exceptional warmth
Great traction
Well made
Keeps feet dry
Comfortable fit
$140 $140
SALE
Men's Snow Sneaker 5 Shoes, Slip-On
L.L.Bean Men's Snow Sneaker 5 Shoes, Slip-On
A black suede-and-fabric winter slip-on with 200-gram insulation, waterproof membrane, moisture-wicking lining, and rugged traction.
(619)
$130 $130
SALE
What customers like:
High quality
Comfortable design
Roomy fit
Durable construction
Excellent warmth
$130 $130
SALE
Men's Maine Hunting Shoes, 10"
L.L.Bean Men's Maine Hunting Shoes, 10"
A brown waterproof leather boot with a steel shank, flexible moccasin-like sole, and improved traction.
(590)
$160 $160
SALE
What customers like:
Favorite boots
Lightweight
Quiet in the woods
Comfortable
Vibrant colors
$160 $160
SALE
Men's Bean's Comfort Fitness Walking Shoes, Waterproof
L.L.Bean Men's Bean's Comfort Fitness Walking Shoes, Waterproof
A blue waterproof walking shoe with breathable mesh, supportive cushioning, and grippy rubber traction for wet-weather comfort.
(543)
$120 $84.99
SALE
What customers like:
Fit
Quality
Comfort
Durability
Arch support
$120 $84.99
SALE
Men's Snow Sneaker 5 Shoes, Lace-Up
L.L.Bean Men's Snow Sneaker 5 Shoes, Lace-Up
A blue suede-and-fabric winter sneaker with waterproof protection, 200-gram insulation, supportive cushioning, and rugged traction.
(516)
$140 $140
SALE
What customers like:
Great fit
Comfortable
Good value
Keeps feet dry
Excellent warmth
$140 $140
SALE
Kids' Trail Model Hikers
L.L.Bean Kids' Trail Model Hikers
A red kids’ hiking shoe with breathable mesh, waterproof membrane, cushioned EVA comfort, and durable traction.
(327)
$79.95 $44.99
SALE
What customers like:
Waterproof
Comfortable for travel
Durable material
Great color options
Good fit
$79.95 $44.99
SALE
Men's Keen® Newport Sandals
Keen Men's Keen® Newport Sandals
A brown waterproof leather sandal with neoprene-lined straps, cushioning and sticky rubber traction for wet adventures.
(294)
$135 $135
SALE
$135 $135
SALE
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 cushioning, arch support, and durable traction for varied trails.
(279)
$175 $175
SALE
What customers like:
Durable construction
High-quality materials
Superior arch support
Comfortable fit
Professional customer service
$175 $175
SALE
Women's Bean's Comfort Fitness Walking Shoes, Waterproof
L.L.Bean Women's Bean's Comfort Fitness Walking Shoes, Waterproof
A gray waterproof shoe with breathable mesh, cushioned support, and grippy rubber traction for stable strides.
(276)
$120 $84.99
SALE
What customers like:
Supportive
Waterproof
Versatile
Comfortable
Well made
$120 $84.99
SALE
Kids' Trail Model Hikers, Low
L.L.Bean Kids' Trail Model Hikers, Low
A blue hiking shoe with water-resistant suede, breathable nylon, cushioned EVA comfort, and grippy rubber traction.
(253)
$64.95 $44.99
SALE
What customers like:
Well-made
Nice appearance
Durable
Versatile
Comfortable
$64.95 $44.99
SALE
Men's Kennebec Slip-On Shoes
L.L.Bean Men's Kennebec Slip-On Shoes
A brown leather slip-on with reliable wet-dry traction, anti-odor comfort, and supportive all-day cushioning.
(238)
$130 $74.99
SALE
What customers like:
High quality
Nice looking
Attractive color
Perfect fit
Comfortable
$130 $74.99
SALE
Women's Keen Newport H2
Keen Women's Keen Newport H2
A blue waterproof sandal with quick-drying nylon, neoprene and rubber, protective toe coverage, and rugged traction.
(213)
$130 $130
SALE
What customers like:
Quality materials
Roomy toe
Light weight
Good arch support
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 brown waterproof leather hiking boot with breathable lining, supportive cushioning, and rugged rubber traction.
(181)
$220 $220
SALE
What customers like:
Light
Sturdy
Comfortable
Good quality orthotic base
Looks great
$220 $220
SALE
Women's Oboz Sawtooth X B-DRY Hikers, Low
Oboz Women's Oboz Sawtooth X B-DRY Hikers, Low
A gray waterproof leather hiking shoe with breathable lining, cushioned support, and reliable multidirectional traction.
(158)
$185 $185
SALE
$185 $185
SALE
Women's Oboz Sawtooth X B-DRY Hikers, Mid
Oboz Women's Oboz Sawtooth X B-DRY Hikers, Mid
A brown waterproof mid hiker with nubuck leather, rubber and nylon construction, cushioning, and mud-shedding traction.
(100)
$200 $200
SALE
What customers like:
Warm for cold conditions
Snug ankle support
Sturdy construction
Comfortable fit
$200 $200
SALE
Toddlers' Trail Model Hikers
L.L.Bean Toddlers' Trail Model Hikers
A gray waterproof toddler hiker with suede-nylon uppers, easy-on straps, cushioning, and grippy rubber traction.
(99)
$64.95 $44.99
SALE
$64.95 $44.99
SALE
Men's Oboz Sawtooth X B-DRY Hikers, Mid
Oboz Men's Oboz Sawtooth X B-DRY Hikers, Mid
A gray waterproof mid hiker with nubuck leather, supportive cushioning, and multidirectional traction for muddy trails.
(93)
$200 $200
SALE
What customers like:
Durable quality
Great support
High comfort
Excellent fitting
Reliable traction
$200 $200
SALE
Men's Trail Model X Waterproof Hiking Shoes, Camo
L.L.Bean Men's Trail Model X Waterproof Hiking Shoes, Camo
A waterproof camo hiking shoe with suede leather, breathable mesh, EVA cushioning, and enhanced wet-surface traction.
(0)
$110 $74.99
SALE
$110 $74.99
SALE
Women's Salomon X Ultra 5 GORE-TEX Hiking Boots
Salomon Women's Salomon X Ultra 5 GORE-TEX Hiking Boots
A gray lightweight GORE-TEX hiking boot offering waterproof protection, all-terrain traction, and stability on technical trails.
(0)
$185 $185
SALE
$185 $185
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 breathable mesh, protective toe, cushioning, and improved wet traction.
(0)
$120 $120
SALE
$120 $120
SALE
Women's Oboz Ousel B-Dry Hiking Shoes
Oboz Women's Oboz Ousel B-Dry Hiking Shoes
A gray leather-and-rubber hiking shoe with waterproof breathable protection, supportive cushioning, and high-traction trail grip.
(0)
$155 $155
SALE
$155 $155
SALE
Women's Elevation Travel Slip-On Shoes, Waterproof
L.L.Bean Women's Elevation Travel Slip-On Shoes, Waterproof
A tan waterproof mesh-and-rubber slip-on with cushioned support, durable traction, and protection from rocks and roots.
(0)
$130 $130
SALE
$130 $130
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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