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Waterproof Trail Boots

Find waterproof trail boots for your next outing, with a selection of styles to explore. Compare fit and sizing information, and check each pair’s waterproof features and recommended use to help choose the right boots for your trail plans.

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Men's Cresta II Waterproof Hiking Boots, Leather
L.L.Bean Men's Cresta II Waterproof Hiking Boots, Leather
A brown leather hiking boot with waterproof membrane and Vibram® sole for rugged, all-weather traction.
(0)
$280 $280
SALE
$280 $280
SALE
Women's Cresta II Waterproof Hiking Boots, Leather
L.L.Bean Women's Cresta II Waterproof Hiking Boots, Leather
A brown leather hiking boot with waterproof membrane, cushioned EVA footbed, and Vibram rubber sole for traction.
(0)
$280 $280
SALE
$280 $280
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 rubber outsole for superior wet traction.
(0)
$130 $130
SALE
$130 $130
SALE
Women's Trail Model X Waterproof Hiking Boots, Leather
L.L.Bean Women's Trail Model X Waterproof Hiking Boots, Leather
A brown leather hiking boot featuring a waterproof upper, rugged rubber outsole, and recycled polyester accents.
(0)
$130 $130
SALE
$130 $130
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 conditions.
(0)
$120 $120
SALE
$120 $120
SALE
Women's Trail Model X Waterproof Hiking Boots
L.L.Bean Women's Trail Model X Waterproof Hiking Boots
A waterproof hiking boot with gray suede leather, rubber sole, and enhanced traction for wet conditions.
(0)
$120 $120
SALE
$120 $120
SALE
Men's Access Hiking Boots, Waterproof
L.L.Bean Men's Access Hiking Boots, Waterproof
A waterproof black hiking boot featuring recycled mesh, nubuck leather, and a grippy VertiGrip Trail outsole.
(0)
$150 $126.99
SALE
$150 $126.99
SALE
Women's Access Hiking Boots, Waterproof
L.L.Bean Women's Access Hiking Boots, Waterproof
A waterproof hiking boot featuring a multi-color mesh, rubber, and leather upper for all-day comfort.
(0)
$150 $150
SALE
$150 $150
SALE
Men's Heritage Hiking Boots, Waterproof
L.L.Bean Men's Heritage Hiking Boots, Waterproof
A retro-inspired gray hiking boot with waterproof suede-and-nylon upper and grippy VertiGrip Trail rubber outsole.
(0)
$150 $109.99
SALE
$150 $109.99
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
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 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
Men's Keen Targhee IV Mid Waterproof Hiking Boots
Keen Men's Keen Targhee IV Mid Waterproof Hiking Boots
A waterproof leather hiking boot offering stability, support, and comfort with eco-friendly features and durable traction.
(0)
$180 $180
SALE
$180 $180
SALE
Men's Storm Chaser Boots 5, Zip
L.L.Bean Men's Storm Chaser Boots 5, Zip
A durable oakwood boot with waterproof leather, PrimaLoft® insulation, and side zips for easy on/off.
(1,216)
$170 $170
SALE
What customers like:
Comfortable for long hours of use
Warmth and insulation
Great traction and water resistance
High quality and durable materials
Easy to put on and take off
$170 $170
SALE
Men's Storm Chaser Boots 5, Leather Lace-Up
L.L.Bean Men's Storm Chaser Boots 5, Leather Lace-Up
A rugged, all-weather black boot with waterproof leather, PrimaLoft® insulation, and a multi-lugged rubber outsole.
(774)
$170 $170
SALE
What customers like:
Perfect fit
Great quality
High comfort
Improved traction
Excellent warmth
$170 $170
SALE
Kids' Northwoods Boots
L.L.Bean Kids' Northwoods Boots
A pair of bold lilac winter boots with removable liners, waterproof rubber bottoms, and reflective trim.
(733)
$79.95 $79.95
SALE
What customers like:
Comfort
Warmth
Durability
Easy to put on and take off
Waterproofing
$79.95 $79.95
SALE
Men's Maine Hunting Shoes, 10"
L.L.Bean Men's Maine Hunting Shoes, 10"
A pair of 10" waterproof leather boots offering superior support and traction for versatile outdoor use.
(590)
$160 $160
SALE
What customers like:
Favorite boots
Lightweight
Quiet in the woods
Comfortable
Warm
$160 $160
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 buttery-soft leather, plush shearling lining, and waterproof rubber bottom for cold conditions.
(425)
$290 $290
SALE
What customers like:
High durability
Made in the USA
Stylish appearance
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 and superior arch support, made from leather, rubber, and nylon.
(279)
$160 $160
SALE
What customers like:
Durable construction
High-quality materials
Superior support
Comfortable fit
Professional customer service
$160 $160
SALE
Men's Bean Boots 8", Flannel-Lined Insulated
L.L.Bean Men's Bean Boots 8", Flannel-Lined Insulated
A brown leather and rubber boot lined with soft flannel, offering warmth, comfort, and waterproof protection.
(264)
$200 $200
SALE
$200 $200
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
Women's Bean Boots, 8" Flannel-Lined Insulated
L.L.Bean Women's Bean Boots, 8" Flannel-Lined Insulated
A brown leather and rubber boot lined with premium flannel and insulation for cozy, waterproof warmth.
(187)
$200 $200
SALE
$200 $200
SALE
Men's Arctic Sport Muck Boots, Mid-Cut
Muck Men's Arctic Sport Muck Boots, Mid-Cut
A waterproof, insulated mid-cut boot with thermal foam, breathable lining, and reinforced outsole for extreme conditions.
(179)
$180 $180
SALE
What customers like:
High durability
Lightweight
All-around use
Watertightness
Keeps feet warm
$180 $180
SALE
Women's Oboz Sawtooth X B-DRY Hikers, Low
Oboz Women's Oboz Sawtooth X B-DRY Hikers, Low
A rugged, waterproof trail shoe with reliable traction and a breathable nubuck leather upper in hazy gray.
(158)
$165 $165
SALE
$165 $165
SALE

Waterproof Trail Boots

Waterproof Trail Boots belong on the shortlist when you’re choosing footwear for time on the trail and want waterproof protection to be part of the design. A familiar path can feel different from one outing to the next: rain lingering on the leaves, damp ground beneath the trees, a favorite overlook waiting around the last bend. Choosing a pair starts with thinking about the trails you enjoy and what you like in a boot, rather than looking for one style to do everything. Consider the height you prefer, the fit you’re accustomed to and the details that matter to you. Waterproof is an important distinction, but it doesn’t tell the whole story of a boot. Read each pair’s description for its specific construction, intended use and care requirements, and let those details guide your comparison alongside its appearance.

Fit deserves just as much attention as the waterproof designation. When trying on trail boots, wear the socks you expect to wear with them and take time to lace both boots before walking around. Your toes should have room to move without your feet sliding forward, and your heels shouldn’t lift excessively with each step. Pay attention to pressure across the top of your foot and around your ankles; a promising fit should not depend on ignoring a spot that already pinches. If you use an insert, check the individual boot’s details for compatibility rather than assuming it will fit. Size guidance and available measurements are useful starting points, especially when comparing styles with boots you already own. Before heading outside, try your pair indoors in keeping with the retailer’s return policy. Those few extra minutes can help you make a more considered choice than a quick try-on while standing still.

For someone who looks forward to a weekend trail outing, waterproof trail boots can also make a thoughtful gift. The most useful starting point is knowing the recipient’s size, preferred fit and the kind of trails they choose—not simply picking the pair you would wear yourself. Perhaps they favor a short loop with the family, or perhaps they like revisiting the same wooded route with a friend through the changing seasons. Let their preferences shape the choice, and consider letting them make the final fit decision. Whether you’re shopping for yourself or someone close to you, look beyond any single feature and compare the full product details. Follow the care instructions for the pair you select, including any directions for cleaning and drying. A well-considered choice leaves more room to look forward to the outing itself: meeting at the trailhead, catching up along the way and taking a moment to enjoy being outside together.

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