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Rugged Trail Shoes

Explore rugged trail shoes in a selection of styles for your next outing. Compare fit, sizing and the features listed for each pair to help you choose shoes that suit your feet and the trails you plan to explore.

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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 Stonington Shoes, Moc-Toes
L.L.Bean Men's Stonington Shoes, Moc-Toes
A rugged dark cocoa leather shoe with sneaker-like comfort, water-resistant protection, and a molded rubber outsole.
(1,369)
$140 $140
SALE
What customers like:
Well-made construction
Lightweight
Versatile design
Water-resistant leather
Comfortable fit
$140 $140
SALE
Men's Bucksport Shoes, Plain Toe
L.L.Bean Men's Bucksport Shoes, Plain Toe
A rugged dark cocoa leather shoe with Vibram® rubber outsoles and waterproof oiled-leather upper for durability.
(835)
$170 $170
SALE
What customers like:
Excellent quality
Durable
Great appearance
Versatile
Comfortable
$170 $170
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 and superior arch support in dark shadow.
(279)
$160 $160
SALE
What customers like:
Well-designed
Durable construction
Advanced cushioning
Superior support
Comfortable fit
$160 $160
SALE
Men's Oboz Bridger Mid B-Dry Hiking Boots
Oboz Men's Oboz Bridger Mid B-Dry Hiking Boots
A rugged, waterproof hiking boot with a leather upper and rubber sole, perfect for challenging 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, 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
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 Waterproof Hiking Boots, Leather
L.L.Bean Men's Trail Model X Waterproof Hiking Boots, Leather
A brown waterproof leather hiking boot with recycled polyester accents and enhanced traction for wet, rugged trails.
(0)
$130 $130
SALE
$130 $130
SALE
Men's Access Hiking Boots, Waterproof
L.L.Bean Men's Access Hiking Boots, Waterproof
A waterproof hiking boot in carbon navy with leather/rubber construction and shock-absorbing foam insole.
(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 brown suede leather hiking shoe with waterproof features and enhanced traction for wet conditions.
(0)
$110 $110
SALE
$110 $110
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 protection, cushioned EVA footbed, and Vibram® rubber sole.
(0)
$280 $280
SALE
$280 $280
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 Access Hiking Shoes, Waterproof
L.L.Bean Men's Access Hiking Shoes, Waterproof
A waterproof hiking shoe with recycled polyester mesh, nubuck leather upper, and VertiGrip Trail rubber outsole.
(0)
$140 $140
SALE
$140 $140
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 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 recycled materials for outdoor adventures.
(0)
$99.95 $99.95
SALE
$99.95 $99.95
SALE
Men's Trail Model X Waterproof Hiking Shoes, Leather
L.L.Bean Men's Trail Model X Waterproof Hiking Shoes, Leather
A rugged brown leather hiking shoe with waterproof protection, enhanced traction, and breathable, recycled materials.
(0)
$120 $120
SALE
$120 $120
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 Urban Storm Shoes, Waterproof Insulated
L.L.Bean Men's Urban Storm Shoes, Waterproof Insulated
A rugged, waterproof, and insulated shoe with leather upper and rubber outsole, ideal for all-weather comfort.
(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 protection and enhanced traction for wet surfaces.
(0)
$120 $120
SALE
$120 $120
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
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 insulation for cold, wet conditions.
(3,695)
$130 $130
SALE
What customers like:
High quality
Versatile design
Easy to slip on
Warm and insulated
Comfortable fit
$130 $130
SALE
Men's Stonington Boots, Moc-Toe
L.L.Bean Men's Stonington Boots, Moc-Toe
A rugged brown leather boot with water-resistant upper, moisture-wicking lining, and sneaker-like comfort.
(1,099)
$170 $170
SALE
$170 $170
SALE
Men's Stonington Oxford Shoes, Plain Toe
L.L.Bean Men's Stonington Oxford Shoes, Plain Toe
A rugged, deepest brown leather shoe with sneaker-like comfort, water-resistant protection, and a molded rubber outsole.
(681)
$140 $140
SALE
What customers like:
Good looking
Rain resistance
Comfort
True to size
Non-slip soles
$140 $140
SALE

Rugged Trail Shoes

Rugged Trail Shoes belong in the kind of outdoor plans that leave room to linger: a favorite trail with a friend, a quiet stretch of woods, or a family outing with plenty of stops to take in the view. Choosing a pair starts with thinking about the trails you enjoy and what you like in a shoe. Consider the shape, the fit and how each style fits into your outdoor wardrobe, rather than choosing on looks alone. A familiar silhouette or an understated color can make the decision easier, but the most useful comparison is between the individual details of each pair. Look closely at the product descriptions and sizing information to find the options that match your preferences.

Fit deserves a little extra attention, especially when you’re replacing an old favorite. Use your current shoes as a starting point: notice where they feel too close, where there’s unwanted space and whether you’ve been wishing for a different shape around the toes. Check the available widths and any style-specific sizing notes before settling on a size. When trying on trail shoes, wear the socks you expect to wear with them, lace both shoes and give yourself time to walk around indoors. Pay attention to pressure across the top of the foot, movement at the heel and room around your toes. Comparing those details is more helpful than assuming that the same size will feel identical in every style.

Trail shoes can also make a thoughtful gift for someone who treasures time outside, whether they’re a regular companion on your favorite route or a family member who always suggests taking the longer way back. With footwear, a little shared decision-making often makes the gift more personal. Knowing the recipient’s usual size is useful, but knowing their preferred width, shape and style matters, too. Invite them to compare a few options rather than guessing about fit. For your own next pair, take the same thoughtful approach: choose a look you genuinely like, check the details that matter to you and keep fit at the center of the decision. The goal is a pair you’ll be glad to have waiting by the door when it’s time to head out together.

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