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Trail Hiking Shoes

Explore trail hiking shoes for your next hike, with a selection of styles to compare. Check each pair’s product details for sizing, fit and features to help you choose footwear that suits your hiking plans.

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Men's Oboz Bridger Low B-Dry Hiking Shoes
Oboz Men's Oboz Bridger Low B-Dry Hiking Shoes
A versatile, waterproof hiking shoe in dark shadow with advanced cushioning and superior arch support.
(279)
$160 $160
SALE
What customers like:
Durable construction
High-quality materials
Superior support
Comfortable fit
Professional customer service
$160 $160
SALE
Men's Oboz Bridger Mid B-Dry Hiking Boots
Oboz Men's Oboz Bridger Mid B-Dry Hiking Boots
A midheight hiking boot with waterproof nubuck leather, breathable membrane, and superior arch support for tricky 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 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 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 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 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 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 eco-friendly materials for outdoor adventures.
(0)
$99.95 $99.95
SALE
$99.95 $99.95
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 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 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
Men's Elevation H2O Shoes
L.L.Bean Men's Elevation H2O Shoes
A lightweight gray water-friendly shoe with breathable nylon/neoprene, convertible heel, and VertiGrip outsole for traction.
(0)
$99.95 $64.99
SALE
$99.95 $64.99
SALE
Women's Access Hiking Shoes, Waterproof
L.L.Bean Women's Access Hiking Shoes, Waterproof
A waterproof hiking shoe with a recycled polyester mesh and nubuck leather upper for all-day comfort.
(0)
$140 $140
SALE
$140 $140
SALE
Men's HOKA Challenger 8 Trail Shoes
HOKA Men's HOKA Challenger 8 Trail Shoes
A lightweight blue trail running shoe featuring a recycled mesh upper, cushioned EVA midsole, and grippy outsole.
(0)
$150 $150
SALE
$150 $150
SALE
Men's Keen Targhee IV Waterproof Hiking Shoes
Keen Men's Keen Targhee IV Waterproof Hiking Shoes
A waterproof leather hiking shoe offering stability, support, and comfort with eco-friendly features and durable traction.
(0)
$170 $170
SALE
$170 $170
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 Trail Model X Waterproof Hiking Shoes
L.L.Bean Men's Trail Model X Waterproof Hiking Shoes
A durable brown suede hiking shoe with waterproof membrane and enhanced traction for wet conditions.
(0)
$110 $110
SALE
$110 $110
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 HOKA Challenger 8 Trail Shoes, GORE-TEX
HOKA Men's HOKA Challenger 8 Trail Shoes, GORE-TEX
A black trail running shoe with GORE-TEX waterproofing, EVA midsole, and 4mm lugs for all-terrain traction.
(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 Access Hiking Boots, Waterproof
L.L.Bean Men's Access Hiking Boots, Waterproof
A blue hiking boot with waterproof leather, grippy rubber outsole, and cushioned, shock-absorbing 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 features and enhanced traction for wet conditions.
(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 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

Trail Hiking Shoes

Trail Hiking Shoes are a good place to start when you’re looking forward to more time on the trail, whether that means revisiting a favorite loop or joining friends for a hike somewhere new. Choosing a pair is personal: your usual size, preferred fit and sense of style all deserve a place in the decision. As you browse the recommended options, look beyond the photograph and read each pair’s sizing notes and product details. Consider what you like about the shoes you already own, along with anything you would change—a little more room at the toes, a different shape or a color that feels more like you. You don’t need an ambitious itinerary to make a thoughtful choice. A familiar trail, a willing companion and an afternoon set aside for hiking are plenty of reason to find a pair that suits you.

Fit deserves particular attention when comparing trail hiking shoes. Start with the listed size and width options rather than assuming every style will feel the same in your usual size. When trying on a pair, wear the socks you expect to hike in, lace both shoes and take time to walk around indoors, following the retailer’s try-on and return requirements. Notice where your toes sit, whether your heels shift and whether there are any spots that pinch or press. A favorite color is worth considering, but it shouldn’t talk you into overlooking a fit that feels wrong. If you’re deciding between two options, return to their individual descriptions and sizing guidance rather than relying on appearance alone. Details vary from pair to pair, and a careful comparison can help you narrow the selection without guessing.

Trail hiking shoes can also be a thoughtful gift for someone who enjoys exploring on foot, from a family member who knows every turn of a local trail to a friend beginning to make hiking part of their weekends. The most useful starting point is knowing what the recipient actually wants, including their size, width and style preferences. Asking for those details needn’t take away the pleasure of the gift; it shows that you’ve paid attention to the person who will wear it. Check the exchange policy before choosing, and consider pairing the gift with an invitation to hike together. There’s something worth looking forward to in a simple plan: meeting at the trailhead, choosing a route together and leaving enough time to stop at the overlook rather than heading straight back.

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