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Mens Slip On Trail Shoes

Find men's slip-on trail shoes for your next trail outing, and browse available styles and sizes. Compare each pair’s fit and construction details to help narrow the selection and choose the right shoes for you.

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Men's Storm Chaser 5 Slip-Ons
L.L.Bean Men's Storm Chaser 5 Slip-Ons
A tough, all-weather slip-on with waterproof leather, rubber outsole, and exceptional cushioning for cold, wet conditions.
(3,695)
$130 $130
SALE
What customers like:
High quality
Warm and cozy
Versatile design
Easy to slip on
Comfortable fit
$130 $130
SALE
Men's Snow Sneaker 5 Shoes, Slip-On
L.L.Bean Men's Snow Sneaker 5 Shoes, Slip-On
A slip-on winter sneaker with ColdShield insulation, stain-resistant suede, and a rugged VertiGrip rubber outsole.
(619)
$130 $130
SALE
What customers like:
High quality
Comfortable design
Roomy fit
Durable construction
Excellent warmth
$130 $130
SALE
Men's Kennebec Slip-On Shoes
L.L.Bean Men's Kennebec Slip-On Shoes
A versatile slip-on with premium full-grain leather, True Comfort footbed, and VertiGrip outsole for reliable traction.
(238)
$130 $89.99
SALE
What customers like:
High quality
Nice looking
Perfect fit
Attractive style
Comfortable
$130 $89.99
SALE
Men's Bean Boots, Slip-On Rubber Mocs
L.L.Bean Men's Bean Boots, Slip-On Rubber Mocs
A weather-ready slip-on moc with a brown leather upper and waterproof rubber bottom for wet conditions.
(0)
$99.95 $99.95
SALE
$99.95 $99.95
SALE
Men's Elevation Travel Slip-On Shoes, Waterproof
L.L.Bean Men's Elevation Travel Slip-On Shoes, Waterproof
A lightweight green mesh and rubber travel shoe with waterproof protection, breathable comfort, and grippy traction.
(0)
$130 $130
SALE
$130 $130
SALE
Men's Elevation H2O Shoes
L.L.Bean Men's Elevation H2O Shoes
A lightweight gray water-friendly shoe with nylon and neoprene, offering quick-drying comfort and wet/dry traction.
(0)
$99.95 $64.99
SALE
$99.95 $64.99
SALE
Men's HOKA Challenger 8 Trail Shoes, GORE-TEX
HOKA Men's HOKA Challenger 8 Trail Shoes, GORE-TEX
A waterproof black trail shoe featuring a GORE-TEX membrane, EVA midsole, and 4mm multi-directional lugs.
(0)
$165 $165
SALE
$165 $165
SALE
Men's NextVenture Waterproof Slip-On Shoes, Suede
L.L.Bean Men's NextVenture Waterproof Slip-On Shoes, Suede
A brown suede waterproof slip-on with Vibram rubber outsole and cushioned EVA midsole for all-day comfort.
(0)
$150 $150
SALE
$150 $150
SALE
Men's NextVenture Waterproof Slip-On Shoes, Leather
L.L.Bean Men's NextVenture Waterproof Slip-On Shoes, Leather
A brown leather slip-on with waterproof protection, cushioned EVA midsole, and Vibram rubber outsole for traction.
(0)
$150 $150
SALE
$150 $150
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:
Fit
Quality
Comfort
Style
Versatility
$140 $140
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 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 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 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 Bean Boots, Rubber Mocs
L.L.Bean Men's Bean Boots, Rubber Mocs
A Maine-made slip-on boot with waterproof rubber bottom, supple leather upper, and durable chain-tread outsole.
(0)
$99.95 $99.95
SALE
$99.95 $99.95
SALE
Men's Allagash Handsewn Mocs, One-Eye
L.L.Bean Men's Allagash Handsewn Mocs, One-Eye
A durable brown moccasin with full-grain leather, ergonomic footbed, and lightweight rubber outsole.
(0)
$150 $150
SALE
$150 $150
SALE
Men's HOKA Transport 2 Shoes
HOKA Men's HOKA Transport 2 Shoes
A versatile gray athleisure shoe featuring recycled polyester, water-repellent treatment, and a Vibram EcoStep outsole.
(0)
$150 $150
SALE
$150 $150
SALE
Men's 1985 Mountain Classic Sneakers
L.L.Bean Men's 1985 Mountain Classic Sneakers
A water-resistant black sneaker with suede, recycled nylon, and rugged VertiGrip rubber outsole for outdoor traction.
(0)
$110 $79.99
SALE
$110 $79.99
SALE
Men's On Cloudvista Trail Running Shoes
On Men's On Cloudvista Trail Running Shoes
A lightweight gray trail running shoe featuring breathable mesh, Helion™ superfoam cushioning, and Missiongrip™ rubber traction.
(0)
$150 $150
SALE
$150 $150
SALE
Men's On Cloudsurfer Trail 2 Running Shoes
On Men's On Cloudsurfer Trail 2 Running Shoes
A lightweight gray trail running shoe featuring a cushioned Helion™ midsole and durable Missiongrip™ rubber outsole.
(0)
$170 $170
SALE
$170 $170
SALE

Mens Slip On Trail Shoes

There’s something to look forward to in a familiar trail: the bend beneath the trees, the view across the pond, the chance to spend a little time outside together. Our Mens Slip On Trail Shoes selection brings a straightforward footwear style to that outdoor tradition. When browsing, start with the details that matter to you personally, from the shape of the shoe to the way it looks alongside your favorite pants. A streamlined profile and a more substantial silhouette can have quite different appeal, even within the same category. Look closely at the photos from several angles, and consider whether you prefer understated colors or a more noticeable contrast between the upper and sole. The right choice should feel like your style, rather than something you have to build a whole wardrobe around.

Choosing men’s slip-on trail shoes also means giving fit a little extra attention. Without laces to adjust, it’s worth reading the sizing information for each pair instead of assuming your usual size tells the whole story. Check the available widths and any item-specific fit notes, and think about the socks you expect to wear with them. When trying shoes on, take time to notice how they feel through the heel, across the top of the foot and around the toes; don’t judge the fit only while sitting down. For trail plans, let the individual shoe’s description help inform your choice rather than relying on appearance alone. A short loop with family and a longer route through unfamiliar terrain call for different considerations, and the details on each listing are a useful place to begin that comparison.

Slip-on trail shoes can also be a thoughtful gift for someone who enjoys making time for the outdoors, whether that’s your dad, your partner or a friend who always suggests a walk when everyone gets together. The most personal choice often comes from noticing what they already like: the colors they reach for, the shoe shapes they favor and whether they regularly choose slip-on styles. Confirm their size and width when possible, and check the exchange details before deciding. Picture the everyday moments behind the gift—the shoes waiting by the door, the invitation to revisit a favorite path, the conversation that carries on long after the walk ends. Keeping that person’s preferences at the center of the decision makes the selection more meaningful than simply choosing the pair you would pick for yourself.

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