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Trail Footwear

Shop trail footwear from L.L.Bean to find your next pair for the trail. Browse styles and compare sizing, fit information and individual product features to choose footwear that suits your plans.

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Men's Elevation Trail Shoes, Waterproof
L.L.Bean Men's Elevation Trail Shoes, Waterproof
A blue waterproof trail shoe with recycled polyester mesh, rock protection and grippy rubber traction.
(0)
$130 $130
SALE
$130 $130
SALE
Women's Elevation Trail Shoes, Waterproof
L.L.Bean Women's Elevation Trail Shoes, Waterproof
A lightweight green waterproof trail shoe with recycled mesh, rock plate and grippy rubber outsole.
(0)
$130 $130
SALE
$130 $130
SALE
Women's HOKA Challenger 8 Trail Shoes, GORE-TEX
HOKA Women's HOKA Challenger 8 Trail Shoes, GORE-TEX
A gray trail-running shoe with recycled mesh, GORE-TEX protection, cushioned EVA midsoles, and 4mm lugs.
(0)
$165 $165
SALE
$165 $165
SALE
Men's HOKA Challenger 8 Trail Shoes
HOKA Men's HOKA Challenger 8 Trail Shoes
A blue trail running shoe with rRPET mesh, cushioned EVA midsole, reflective details, and 4mm lugs.
(0)
$150 $150
SALE
$150 $150
SALE
Men's Oboz Sawtooth X B-DRY Hikers, Low
Oboz Men's Oboz Sawtooth X B-DRY Hikers, Low
A brown hiking shoe with waterproof B-DRY lining, nubuck leather, supportive nylon shank, and mud-shedding traction.
(0)
$185 $185
SALE
$185 $185
SALE
Women's Oboz Sawtooth X B-DRY Hikers, Low
Oboz Women's Oboz Sawtooth X B-DRY Hikers, Low
A gray waterproof hiking shoe with breathable nubuck leather, mud-shedding lugs and supportive cushioning.
(158)
$185 $185
SALE
$185 $185
SALE
Men's On Cloudvista Trail Running Shoes
On Men's On Cloudvista Trail Running Shoes
A gray trail-running shoe with sticky rubber traction, responsive cushioning, and a lightweight mesh upper.
(0)
$150 $150
SALE
$150 $150
SALE
Women's HOKA Challenger 8 Trail Shoes
HOKA Women's HOKA Challenger 8 Trail Shoes
A blue trail-running shoe with high cushioning, recycled polyester mesh, reflective details, and 4mm lugs.
(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 waterproof hiking shoe with a suede-and-rubber upper, rock plate, cushioned midsole, and wet-grip outsole.
(0)
$110 $110
SALE
$110 $110
SALE
Men's Trail Model X Waterproof Hiking Shoes, Camo
L.L.Bean Men's Trail Model X Waterproof Hiking Shoes, Camo
A camouflage waterproof hiking shoe with suede leather, cushioned EVA, and grippy rubber outsoles.
(0)
$110 $74.99
SALE
$110 $74.99
SALE
Men's Oboz Bridger Low B-Dry Hiking Shoes
Oboz Men's Oboz Bridger Low B-Dry Hiking Shoes
A gray leather hiking shoe with waterproof protection, cushioned support, and durable traction for trail adventures.
(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 Trail Model X Waterproof Hiking Shoes, Leather
L.L.Bean Women's Trail Model X Waterproof Hiking Shoes, Leather
A brown waterproof leather hiking shoe with a grippy rubber outsole, rock plate and cushioned comfort.
(0)
$120 $120
SALE
$120 $120
SALE
Men's Oboz Sawtooth X B-DRY Hikers, Mid
Oboz Men's Oboz Sawtooth X B-DRY Hikers, Mid
A gray mid-height hiking boot with waterproof lining, nubuck leather, and multidirectional traction for rugged trails.
(93)
$200 $200
SALE
What customers like:
Great fitting
Excellent support
High comfort
Superior quality
$200 $200
SALE
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 a waterproof membrane, Vibram® traction, and cushioned comfort for trails.
(0)
$280 $280
SALE
$280 $280
SALE
Men's On Cloudvista 3 Trail Running Shoes
On Men's On Cloudvista 3 Trail Running Shoes
A white trail-running shoe with Helion superfoam cushioning, Speedboard rebound, and Missiongrip traction for mixed terrain.
(0)
$160 $160
SALE
$160 $160
SALE
Women's On Cloudvista Trail Running Shoes
On Women's On Cloudvista Trail Running Shoes
A green trail-running shoe with lightweight mesh, responsive cushioning, and grippy rubber traction for moderate terrain.
(0)
$160 $160
SALE
$160 $160
SALE
Men's Trail Model X Ventilated Hiking Shoes
L.L.Bean Men's Trail Model X Ventilated Hiking Shoes
A brown suede hiking shoe with breathable mesh, water resistance, rock protection, and wet-grip rubber traction.
(0)
$99.95 $69.99
SALE
$99.95 $69.99
SALE
Men's Access Hiking Shoes, Waterproof
L.L.Bean Men's Access Hiking Shoes, Waterproof
A blue waterproof hiking shoe with nubuck leather, recycled mesh, cushioned support, and grippy trail traction.
(0)
$140 $94.99
SALE
$140 $94.99
SALE
Men's On Cloudsurfer Trail 2 Running Shoes
On Men's On Cloudsurfer Trail 2 Running Shoes
A lightweight gray trail running shoe with Helion cushioning, protective abrasion resistance, and grippy rubber outsole.
(0)
$170 $170
SALE
$170 $170
SALE
Women's Oboz Ousel B-Dry Hiking Shoes
Oboz Women's Oboz Ousel B-Dry Hiking Shoes
A gray leather hiking shoe with waterproof breathable protection, supportive cushioning and high-traction rubber for trails.
(0)
$155 $155
SALE
$155 $155
SALE
Women's On Cloudvista 3 Trail Running Shoes
On Women's On Cloudvista 3 Trail Running Shoes
A white trail running shoe with sticky traction, breathable construction, softer cushioning and responsive rebound.
(0)
$160 $160
SALE
$160 $160
SALE
Women's Access Hiking Shoes, Waterproof
L.L.Bean Women's Access Hiking Shoes, Waterproof
A blue waterproof hiking shoe with recycled mesh, nubuck leather, cushioned support and grippy trail traction.
(0)
$140 $94.99
SALE
$140 $94.99
SALE
Women's NextVenture Hiking Shoes, Waterproof
L.L.Bean Women's NextVenture Hiking Shoes, Waterproof
A blue waterproof hiking shoe with mesh, leather and rubber construction, cushioned comfort and trail traction.
(0)
$150 $150
SALE
$150 $150
SALE
Women's Trail Model X Ventilated Hiking Shoes
L.L.Bean Women's Trail Model X Ventilated Hiking Shoes
A purple hiking shoe with water-resistant suede, breathable mesh, protective rock plate, and grippy rubber outsole.
(0)
$99.95 $99.95
SALE
$99.95 $99.95
SALE

Trail Footwear

Trail footwear belongs to the part of getting outside that starts before reaching the trailhead: deciding where to go, making time to meet a friend, and choosing what to bring along. A familiar loop through the trees can be just as welcome as a path somewhere new, especially when the outing leaves room for conversation and a few stops to take in the view. Choosing footwear for those moments is a personal decision, shaped by fit, preferences, and the trails that keep drawing someone back. This collection brings trail footwear together in one place, offering a starting point for comparing styles and finding an option that feels right for the person wearing it. The category name provides a useful starting point, but individual descriptions matter when deciding between options. Footwear grouped under the same theme should not be assumed to have identical construction, sizing, care requirements, or intended uses. Looking beyond appearance helps make the comparison more meaningful, whether the search begins with a favorite silhouette or a particular fit preference. Someone who enjoys returning to the same woodland path may approach the choice differently from someone who likes planning a visit to an unfamiliar trail. Both can start with the same practical consideration: how a particular pair fits into their own plans and preferences. There is no need to choose according to someone else’s pace or ambitions. The shared pleasure of being outside can mean an unhurried afternoon with family, a regular meeting with a friend, or simply another chance to notice a bend in the path that looks different from a new angle. Trail footwear is part of preparing for that experience, not a measure of how far someone goes. Timeless styling, quality, and a considered fit offer a more personal starting point than choosing solely by looks or following another person’s favorite.

Fit deserves close attention because a familiar size is only the beginning of a footwear decision. Comparing the listed size information with the fit of footwear already worn regularly can help establish a starting point, while any style-specific sizing notes deserve a careful read. Different people prefer different amounts of room, and the shape of a pair matters alongside the number on its label. During a try-on, wear the socks intended for the outing and take time to check both feet rather than judging from a quick slip-on. Notice where the toes sit, how the heel feels, and whether any area presses or rubs. A pair that looks right still needs to feel right to the person wearing it; choosing a different size is not necessarily the answer to every fit issue. If an orthotic or another prescribed insert is part of someone’s usual routine, its compatibility with a particular style is another detail to confirm rather than assume. These small considerations make comparisons more useful without turning the choice into a technical exercise. Appearance matters, too, and personal taste is a reasonable part of the decision. A straightforward design may appeal to someone who likes familiar essentials, while another person may be drawn to a different shape or set of details. Neither preference replaces the need to review the individual description. Construction and material information belong in that closer comparison, where the details can be understood in relation to one particular option instead of treated as promises about the entire category. The same approach applies to intended use: match the stated purpose of the footwear to the outing being planned, rather than relying on the word “trail” alone. A route description, a trail map, and a clear sense of the day’s plans provide useful context for that decision. Whether the destination is a well-known local trail or a place suggested by a friend, choosing thoughtfully starts with the person, the fit, and the details provided for the pair under consideration.

Care is another worthwhile consideration when comparing trail footwear, particularly for someone who prefers a simple routine. Read the care directions for the individual pair before choosing a cleaning method or treatment, since instructions can differ with construction and materials. A routine borrowed from another pair may not be appropriate, even when the two look similar. Following the stated directions takes the guesswork out of care and gives the owner a clear reference after an outing. It is also worth paying attention to condition over time rather than assuming that every pair will wear in the same way. Durability cannot be judged from a category name or appearance alone; individual construction details, care guidance, and the way footwear is used all deserve consideration. Keeping those details in mind makes quality a more useful part of the shopping decision than a broad promise about how long something will last. For a gift, trail footwear can be a thoughtful choice for someone whose favorite plans often include time outside, but personal fit makes a little advance knowledge especially valuable. Knowing the recipient’s usual size is helpful; knowing their fit preferences and the styles they have been considering is better. A shared selection can be part of the gift, giving the recipient a say in something they will wear. The occasion does not need to be elaborate: an invitation to revisit a favorite trail together can give the choice a personal connection. For anyone considering the rest of an outfit, Trail Wear offers a related collection to explore alongside footwear, with individual details to review in the same thoughtful way. The aim is a selection that reflects real preferences and real plans, rather than a checklist of features that may not matter to the wearer. A little attention before heading out leaves more room for the parts of the day worth remembering: conversation at the trailhead, a pause beneath the trees, and the decision to come back again.
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