Skip to main content

It's time to upgrade your browser

Your current browser is no longer supported on llbean.com. Please upgrade to one of the following for a smoother, safer shopping experience with us:

Comfortable Trail Footwear

Find comfortable trail footwear for your next outing, with a selection of styles to explore. Compare each pair’s fit guidance, available sizes and product details to narrow your choices and find the right footwear for you.

Read More
Men's Storm Chaser 5 Slip-Ons
L.L.Bean Men's Storm Chaser 5 Slip-Ons
A brown waterproof leather and rubber slip-on offering warmth, odor control, and superior grip in wet conditions.
(3,695)
$130 $130
SALE
$130 $130
SALE
Men's Storm Chaser Boots 5, Zip
L.L.Bean Men's Storm Chaser Boots 5, Zip
A gray all-weather boot with waterproof leather, PrimaLoft® insulation, and easy on/off side zip.
(1,216)
$170 $170
SALE
What customers like:
Comfortable for long hours of use
Great fit and support
Warmth and effective in cold weather
High quality materials and construction
Easy to put on and take off
$170 $170
SALE
Men's Stonington Boots, Moc-Toe
L.L.Bean Men's Stonington Boots, Moc-Toe
A rugged black leather boot with sneaker-like comfort, moisture-wicking lining, and durable rubber outsole.
(1,099)
$170 $124.99
SALE
What customers like:
Durable construction
Lightweight design
Stylish appearance
Quick break-in
Comfortable fit
$170 $124.99
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 Maine Hunting Shoes, 10"
L.L.Bean Men's Maine Hunting Shoes, 10"
A 10" waterproof leather boot offering superior support and traction, ideal for hunting or daily wear.
(590)
$160 $160
SALE
What customers like:
Favorite boots
Lightweight
Quiet in the woods
Comfortable
Warm
$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 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 Bean Boots, 8" Shearling-Lined Insulated
L.L.Bean Men's Bean Boots, 8" Shearling-Lined Insulated
A Maine-made boot with plush shearling lining, waterproof leather, and reliable traction for cold conditions.
(425)
$290 $290
SALE
What customers like:
High durability
Waterproof quality
Made in the USA
Excellent warmth
Comfortable fit
$290 $290
SALE
Men's Oboz Bridger Low B-Dry Hiking Shoes
Oboz Men's Oboz Bridger Low B-Dry Hiking Shoes
A durable, waterproof hiking shoe with advanced cushioning, superior arch support, and a protective rubber toe cap.
(279)
$160 $160
SALE
What customers like:
High quality
Durable construction
Superior support
Comfortable fit
Professional customer service
$160 $160
SALE
Women's Bean's Comfort Fitness Walking Shoes, Waterproof
L.L.Bean Women's Bean's Comfort Fitness Walking Shoes, Waterproof
A weatherproof, cushioned walking shoe with a breathable mesh upper and durable VertiGrip rubber outsole.
(276)
$120 $99.99
SALE
What customers like:
Supportive
Waterproof
Versatile
Comfortable
Well made
$120 $99.99
SALE
Men's Bean Boots 8", Flannel-Lined Insulated
L.L.Bean Men's Bean Boots 8", Flannel-Lined Insulated
A Maine-made boot with premium leather, flannel lining, and waterproof rubber bottom for cold, wet conditions.
(264)
$200 $200
SALE
What customers like:
Great fit
Light
Durable
Warm
Comfortable
$200 $200
SALE
Men's Kennebec Slip-On Shoes
L.L.Bean Men's Kennebec Slip-On Shoes
A versatile dark earth leather slip-on with True Comfort footbed and VertiGrip outsole for all-day wear.
(238)
$130 $89.99
SALE
What customers like:
High quality
Nice looking
Attractive color
Perfect fit
Comfortable
$130 $89.99
SALE
Women's Keen Newport H2
Keen Women's Keen Newport H2
A versatile water shoe with quick-drying nylon, superior toe protection, and enhanced traction for varied terrain.
(213)
$130 $130
SALE
What customers like:
Quality materials
Roomy toe
Light weight
Good arch support
Comfortable fit
$130 $130
SALE
Men's Kangaroo Upland Hunter's Boots, Insulated
L.L.Bean Men's Kangaroo Upland Hunter's Boots, Insulated
A brown kangaroo leather hunting boot with waterproof lining, Primaloft insulation, and Vibram Mega-Grip outsole.
(190)
$280 $280
SALE
What customers like:
Warm insulation
Durable leather
No break-in required
Comfortable fit
Excellent traction
$280 $280
SALE
Men's Oboz Bridger Mid B-Dry Hiking Boots
Oboz Men's Oboz Bridger Mid B-Dry Hiking Boots
A waterproof, all-leather hiking boot with superior arch support and a durable rubber sole for tricky trails.
(181)
$200 $200
SALE
What customers like:
Good quality
Light
Sturdy
Comfortable
Looks great
$200 $200
SALE
Men's Kangaroo Upland Hunter's Boots, Uninsulated
L.L.Bean Men's Kangaroo Upland Hunter's Boots, Uninsulated
A pair of lightweight, brown leather hunting boots with improved traction and waterproof lining for all-day comfort.
(178)
$260 $260
SALE
What customers like:
Boots keep feet dry
Well-made
Comfort
Durability
Great performance in wet and tough conditions
$260 $260
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 protection, breathable nubuck leather, and reliable traction for wet surfaces.
(158)
$165 $165
SALE
$165 $165
SALE
Men's Teva Omnium 2 Leather Sandals
Teva Men's Teva Omnium 2 Leather Sandals
A rugged brown sandal with waterproof leather straps and a nonmarking Spider Rubber outsole for stability.
(148)
$100 $100
SALE
What customers like:
Durable construction
Good fit
Comfortable to wear
$100 $100
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 nubuck leather, breathable lining, and multi-directional traction lugs.
(100)
$180 $180
SALE
What customers like:
Snug ankle support
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 for muddy or wet trails.
(93)
$180 $180
SALE
What customers like:
Great fitting
Excellent support
High comfort
Reliable traction
Superior quality
$180 $180
SALE
Men's Apex Wading Boots, Studded
L.L.Bean Men's Apex Wading Boots, Studded
A pair of studded gray wading boots with Aramid fibers and Vibram Idrogrip rubber soles for superior traction.
(18)
$250 $250
SALE
$250 $250
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
Women's Elevation H2O Shoes
L.L.Bean Women's Elevation H2O Shoes
A lightweight green water-friendly shoe with a breathable nylon/neoprene upper and cushioned EVA midsole.
(0)
$99.95 $64.99
SALE
$99.95 $64.99
SALE
Women's Salomon X Ultra 5 GORE-TEX Hiking Boots
Salomon Women's Salomon X Ultra 5 GORE-TEX Hiking Boots
A lightweight gray hiking boot featuring GORE-TEX waterproofing, advanced support, and all-terrain Contagrip traction.
(0)
$185 $185
SALE
$185 $185
SALE
Women's Trail Model X Waterproof Hiking Shoes
L.L.Bean Women's Trail Model X Waterproof Hiking Shoes
A gray suede leather hiking shoe with waterproof protection and enhanced traction for wet conditions.
(0)
$110 $110
SALE
$110 $110
SALE

Comfortable Trail Footwear

Comfortable Trail Footwear belongs in those simple plans that give you something to look forward to: a familiar path through the woods, a morning with a friend, or a family outing where everyone has time to stop and take in the view. Choosing a pair starts with your own preferences, not someone else’s idea of what trail footwear should look or feel like. Think about the styles you already enjoy wearing, the fit you tend to prefer, and the trails that keep drawing you back outside. A favorite pair can be as much about feeling like yourself as it is about finding the right size. As you browse, look beyond the photograph and compare each option’s sizing information and fit notes. Those details help narrow a broad selection to footwear worth trying on, whether you’re choosing your first trail pair or replacing an old favorite.

Comfort is personal, and a little extra attention when trying on footwear can make the choice clearer. Start with your usual size, then check the individual sizing guidance rather than assuming every style fits the same way. Try both shoes with the socks you expect to wear, take a few steps, and notice how your heels and toes feel. Your toes shouldn’t feel crowded, and you shouldn’t need to curl them to keep the footwear in place. Pay attention to pressure across the top of your foot as well as along the sides; a pair that looks right still needs to feel right on both feet. If you use your own inserts, check the product details for compatibility before purchasing. Give yourself time to compare options without letting a favorite color settle the decision too soon. The best place to begin is with a fit you feel good about, then a style you’ll be happy to reach for.

Trail footwear can also make a thoughtful gift for someone who treasures time outside—the partner who suggests a walk every weekend, the friend who always knows another path to explore, or the family member who would rather share an afternoon outdoors than a busy schedule indoors. Because fit is so individual, it helps to know more than their shoe size. A preferred style, a familiar fit, or a pair they’ve already expressed interest in gives you a more useful starting point. Choosing together can be part of the gift, especially when there’s a trail outing to look forward to afterward. Keep their taste at the center of the decision, whether that means understated colors or a more distinctive look. A well-considered choice reflects the person receiving it—and the ordinary, memorable moments they enjoy outside.

Read More

FAQs