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Mid Trail Shoes

Browse mid trail shoes for a mid-height alternative to low-cut styles. Compare each pair’s design, sizing and fit guidance to narrow your options, and check individual product descriptions for details that matter to you.

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Men's Oboz Sawtooth X B-DRY Hikers, Mid
Oboz Men's Oboz Sawtooth X B-DRY Hikers, Mid
A gray waterproof leather-and-nylon hiker with supportive cushioning and multidirectional traction for muddy, wet trails.
(93)
$180 $180
SALE
What customers like:
Great support
High comfort
Excellent fitting
Reliable traction
Superior quality
$180 $180
SALE
Women's Oboz Sawtooth X B-DRY Hikers, Mid
Oboz Women's Oboz Sawtooth X B-DRY Hikers, Mid
A brown leather mid hiker with waterproof protection, breathable lining, and mud-shedding traction for rugged trails.
(100)
$180 $180
SALE
What customers like:
Warmth for cold conditions
Snug ankle support
Sturdy construction
Comfortable fit
$180 $180
SALE
Women's Oboz Bridger Mid B-Dry Hiking Boots
Oboz Women's Oboz Bridger Mid B-Dry Hiking Boots
A gray leather hiking boot with waterproof-breathable protection, cushioned arch support, and rugged rubber traction.
(0)
$200 $200
SALE
$200 $200
SALE
Men's Oboz Bridger Mid B-Dry Hiking Boots
Oboz Men's Oboz Bridger Mid B-Dry Hiking Boots
A brown leather hiking boot with waterproof breathable protection, supportive cushioning, and rugged rubber traction.
(181)
$200 $200
SALE
What customers like:
Light
Sturdy
Comfortable
Good quality orthotic base
Looks great
$200 $200
SALE
Men's Keen Targhee IV Mid Waterproof Hiking Boots
Keen Men's Keen Targhee IV Mid Waterproof Hiking Boots
A multicolor, waterproof mid hiking boot with nubuck leather, breathable mesh, and cushioning for outdoor adventures.
(0)
$180 $180
SALE
$180 $180
SALE
Women's Keen Targhee IV Mid Waterproof Hiking Boots
Keen Women's Keen Targhee IV Mid Waterproof Hiking Boots
A brown leather waterproof hiking boot with cushioned support, heel stability, and durable multidirectional traction.
(0)
$180 $180
SALE
$180 $180
SALE
Men's HOKA Challenger 8 Trail Shoes
HOKA Men's HOKA Challenger 8 Trail Shoes
A blue trail shoe with recycled polyester mesh, cushioned EVA midsole, reflective details, and 4mm lugs.
(0)
$150 $150
SALE
$150 $150
SALE
Men's Trail Model X Waterproof Hiking Shoes, Camo
L.L.Bean Men's Trail Model X Waterproof Hiking Shoes, Camo
A waterproof camo hiking shoe with suede upper, cushioned EVA midsole, and high-traction rubber outsole.
(0)
$110 $92.99
SALE
$110 $92.99
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 breathable mesh, cushioned EVA comfort and enhanced wet-surface traction.
(0)
$120 $120
SALE
$120 $120
SALE
Men's On Cloudsurfer Trail 2 Running Shoes
On Men's On Cloudsurfer Trail 2 Running Shoes
A gray trail shoe with a breathable, abrasion-resistant upper, cushioned foam midsole, and grippy rubber outsole.
(0)
$170 $170
SALE
$170 $170
SALE
Men's Trail Model X Waterproof Hiking Shoes
L.L.Bean Men's Trail Model X Waterproof Hiking Shoes
A gray suede leather hiking shoe with waterproof protection, rubber toe and outsole, and cushioned comfort.
(0)
$110 $110
SALE
$110 $110
SALE
Women's Trail Model X Waterproof Hiking Shoes, Leather
L.L.Bean Women's Trail Model X Waterproof Hiking Shoes, Leather
A brown leather waterproof hiking shoe with cushioned support, rock-plate protection and enhanced wet-surface traction.
(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 waterproof trail shoe with recycled mesh, EVA cushioning, reflective details, and grippy 4mm lugs.
(0)
$165 $165
SALE
$165 $165
SALE
Men's On Cloudvista 3 Trail Running Shoes
On Men's On Cloudvista 3 Trail Running Shoes
A white trail shoe with breathable upper, Helion superfoam cushioning, and Missiongrip traction for mixed terrain.
(0)
$160 $160
SALE
$160 $160
SALE
Men's Keen Targhee IV Waterproof Hiking Shoes
Keen Men's Keen Targhee IV Waterproof Hiking Shoes
A waterproof leather hiking shoe with stability, support, cushioning and multidirectional traction for all-terrain adventures.
(0)
$170 $170
SALE
$170 $170
SALE
Women's HOKA Challenger 8 Trail Shoes, GORE-TEX
HOKA Women's HOKA Challenger 8 Trail Shoes, GORE-TEX
A gray waterproof trail shoe with GORE-TEX, recycled mesh, cushioned EVA, reflective details, and 4mm lugs.
(0)
$165 $165
SALE
$165 $165
SALE
Women's On Cloudvista 3 Trail Running Shoes
On Women's On Cloudvista 3 Trail Running Shoes
A white trail running shoe with Helion superfoam cushioning, a breathable upper and sticky Missiongrip traction.
(0)
$160 $160
SALE
$160 $160
SALE
Women's Trail Model X Waterproof Hiking Shoes
L.L.Bean Women's Trail Model X Waterproof Hiking Shoes
A gray suede-and-rubber hiking shoe with waterproof protection, enhanced wet traction, cushioning, and protective toe-and-rock plate.
(0)
$110 $110
SALE
$110 $110
SALE
Women's HOKA Challenger 8 Trail Shoes
HOKA Women's HOKA Challenger 8 Trail Shoes
A blue trail shoe with a recycled mesh upper, cushioned EVA midsole, reflective details, and grippy 4mm lugs.
(0)
$150 $150
SALE
$150 $150
SALE
Women's Keen Targhee IV Waterproof Hiking Shoes
Keen Women's Keen Targhee IV Waterproof Hiking Shoes
A gray nubuck leather hiking shoe with waterproof protection, cushioned support, and multidirectional traction.
(0)
$170 $170
SALE
$170 $170
SALE
Men's NextVenture Hiking Shoes, Waterproof
L.L.Bean Men's NextVenture Hiking Shoes, Waterproof
A tan waterproof leather-and-rubber hiking shoe with cushioned EVA comfort and Vibram traction for wet trails.
(0)
$150 $150
SALE
$150 $150
SALE
Men's Access Hiking Shoes, Waterproof
L.L.Bean Men's Access Hiking Shoes, Waterproof
A blue waterproof hiking shoe with leather, recycled mesh, cushioned support, and grippy traction for trails.
(0)
$140 $119.99
SALE
$140 $119.99
SALE
Men's Elevation Trail Shoes, Waterproof
L.L.Bean Men's Elevation Trail Shoes, Waterproof
A blue waterproof trail shoe with recycled mesh, rock protection, cushioned comfort and grippy rubber traction.
(0)
$130 $130
SALE
$130 $130
SALE
Men's Trail Model X Ventilated Hiking Shoes
L.L.Bean Men's Trail Model X Ventilated Hiking Shoes
A gray suede hiking shoe with breathable mesh, water resistance, rock plate, and grippy rubber outsole.
(0)
$99.95 $99.95
SALE
$99.95 $99.95
SALE

Mid Trail Shoes

Mid trail shoes bring a mid-cut silhouette to trail footwear, giving shoppers a distinct choice alongside lower-cut shoes and taller boots. The word “mid” generally refers to the height of the upper around the ankle, not a particular material, weight, or level of performance. That distinction matters because shoes with a similar outline can feel quite different on the foot. A mid-cut shape may appeal to someone who prefers footwear that sits higher around the ankle or simply likes the proportions of this style. It does not, on its own, establish how a shoe will perform on a particular trail. The individual design and its stated purpose tell more of that story. For anyone who enjoys time outside, choosing trail shoes is also a personal decision: familiar paths, favorite companions, and the simple pleasure of making room for another outing all help shape what feels like the right choice. Picture meeting a friend at the trailhead, unfolding a map with the family, or returning to a path that has become part of a weekend tradition. Those moments give the search for footwear a purpose beyond appearance. Within the mid trail shoe category, overall shape, collar height, sizing information, and construction details provide useful points of comparison without making every pair interchangeable. Some shoppers begin with a familiar silhouette; others are exploring a different cut after years of wearing lower shoes. Either starting point leaves room for personal preferences about fit and style. A clearly described shoe makes it easier to distinguish the features that matter from details that simply look appealing in a photograph. The most useful choice is not necessarily the one with the longest list of features, but the one whose individual description matches the intended trail use and whose fit suits the person wearing it. Quality, versatility, and an enduring outdoor look offer a starting point, while the details of each pair deserve a closer look.

Fit gives that comparison a more personal dimension, especially with a shoe that extends around the ankle. Length is only one part of the picture; width, toe space, heel fit, and the feel of the collar can influence whether a particular shape suits a particular foot. Two people who wear the same numbered size may prefer different shoes, and a familiar size does not mean every design will feel identical. The socks someone expects to wear are also part of the fit, so a try-on is more meaningful with that familiar combination than with an entirely different pair. There is value in noticing the small things: whether the toes have room rather than feeling crowded, whether the heel shifts noticeably, and whether the upper presses against the ankle when the foot bends. These are personal observations, not qualities that a category name can promise. Someone replacing a well-loved pair may already know which aspects of the fit they want to keep, while a shopper choosing mid-cut footwear for the first time may need to compare shapes more deliberately. Size charts and any shoe-specific fit notes help put those preferences into context. Appearance has a place in the decision, too. The proportions of the toe, the outline of the upper, and the arrangement of the laces can make otherwise similar trail shoes look distinctly different. A straightforward outdoor style may feel familiar without needing to imitate footwear already in the closet. Shoppers exploring a separate running-footwear category can also browse Midsole Running Shoes; midsole and mid-cut describe different parts of a shoe and should not be treated as equivalent terms. Keeping that distinction clear helps make comparisons more useful. In mid trail shoes, the starting point remains the cut of the upper, followed by the fit, details, and intended purpose of the individual design.

Materials, construction, care, and durability are further considerations that deserve attention at the shoe level rather than assumptions across the collection. A photograph can show the shape and visible details, but the material description provides information that appearance alone cannot establish. Likewise, the word “trail” identifies the category without making every pair appropriate for every route or outing. The stated intended use of a particular shoe is more informative than its resemblance to another design. For someone with a favorite trail in mind, that information helps keep the comparison connected to an actual plan instead of a broad impression. Care instructions are another practical part of choosing footwear, particularly for shoppers who want to understand the upkeep before making a decision. Cleaning methods can differ by material and construction, so the directions provided for the individual pair should take precedence over a routine borrowed from other shoes. Following those directions also avoids treating every upper, lining, or sole as though it requires the same care. Durability is worth considering with similar care: a substantial-looking silhouette is not a measurement of how long footwear will last, and no single lifespan applies to every wearer. Frequency of use, the demands of the intended outing, and the care a pair receives all belong in that conversation. A person returning regularly to familiar trails may approach the choice differently from someone beginning to make outdoor walks part of family time, but both benefit from clear information and a fit that feels right to them. Mid trail shoes can also be a thoughtful gift for someone who has expressed a preference for this footwear style, especially when their sizing and fit preferences are known. Rather than guessing from appearance alone, the recipient’s experience with footwear offers a better starting point. Whether chosen personally or given with a future shared outing in mind, the appeal is straightforward: a mid-cut trail style, carefully considered details, and another reason to make time together outside.
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