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City Hiking Boots

Find city hiking boots for exploring the city on foot, with styles that fit your everyday wardrobe. Compare individual product details, sizing and fit guidance to help choose the right pair for your city walks.

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Men's Stonington Boots, Moc-Toe
L.L.Bean Men's Stonington Boots, Moc-Toe
A rugged dark oakwood leather boot with sneaker-like comfort, moisture-wicking lining, and durable rubber outsole.
(1,099)
$170 $170
SALE
What customers like:
Durable construction
Versatile use
Lightweight design
Stylish appearance
Comfortable fit
$170 $170
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 nubuck leather upper and reliable traction for muddy trails and rainy walks.
(93)
$180 $180
SALE
What customers like:
Great support
High comfort
Excellent fitting
Superior quality
$180 $180
SALE
Men's Maine Warden's Field Boot
L.L.Bean Men's Maine Warden's Field Boot
A rugged, deepest brown leather boot with GORE-TEX, Primaloft insulation, and Vibram outsole for superior traction.
(0)
$280 $280
SALE
$280 $280
SALE
Men's Portland Boots, Lace-Up
L.L.Bean Men's Portland Boots, Lace-Up
A heritage-inspired dark russet leather boot with a Vibram® rubber outsole for durability and traction.
(0)
$200 $200
SALE
$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 waterproof membrane and Vibram® sole for rugged, all-weather traction.
(0)
$280 $280
SALE
$280 $280
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, breathable mesh panels, and enhanced traction for wet trails.
(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 enhanced traction, breathable mesh panels, and recycled polyester accents.
(0)
$120 $120
SALE
$120 $120
SALE
Men's NextVenture Boots, Lace-Up
L.L.Bean Men's NextVenture Boots, Lace-Up
A tan leather and rubber lace-up boot with waterproof protection, cushioned comfort, and Vibram® traction.
(0)
$170 $170
SALE
$170 $170
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 Access Hiking Boots, Waterproof
L.L.Bean Men's Access Hiking Boots, Waterproof
A waterproof hiking boot in carbon navy with leather/rubber construction and shock-absorbing foam insole.
(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 with outstanding stability, support, and comfort, featuring a durable TPU outsole.
(0)
$170 $170
SALE
$170 $170
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 surfaces.
(0)
$120 $120
SALE
$120 $120
SALE
Women's Camden Hills Alpine Boots
L.L.Bean Women's Camden Hills Alpine Boots
A rugged yet stylish black boot with a full-grain leather upper and cozy wool lining.
(0)
$180 $180
SALE
$180 $180
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 traction for wet trails.
(0)
$130 $130
SALE
$130 $130
SALE
Men's Storm Chaser Boots 5, Zip
L.L.Bean Men's Storm Chaser Boots 5, Zip
A gray all-weather boot with waterproof leather, PrimaLoft® insulation, and easy on/off side zip.
(1,216)
$170 $170
SALE
What customers like:
Comfortable for long hours of use
Great fit and support
Warmth and effective in cold weather
High quality materials and construction
Easy to put on and take off
$170 $170
SALE
Women's Bean Boots, 8" Shearling-Lined Insulated
L.L.Bean Women's Bean Boots, 8" Shearling-Lined Insulated
A multi-color, leather and rubber boot with plush shearling lining for warmth and waterproof protection.
(1,100)
$290 $290
SALE
What customers like:
Waterproof
Well-made
Lightweight
Warmth
Comfortable
$290 $290
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 plush shearling lining, waterproof leather, and reliable traction for cold conditions.
(425)
$290 $290
SALE
What customers like:
High durability
Waterproof quality
Made in the USA
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 versatile, waterproof hiking shoe with advanced cushioning and superior arch support in dark shadow.
(279)
$160 $160
SALE
What customers like:
Well-designed
Durable construction
Advanced cushioning
Superior support
Comfortable fit
$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 and insulation for warmth and waterproof protection.
(264)
$200 $200
SALE
What customers like:
High quality leather and materials
Warm and well-insulated
Attractive style and color options
Comfortable fit with no break-in required
Well made and durable
$200 $200
SALE
Women's Oboz Sawtooth X B-DRY Hikers, Mid
Oboz Women's Oboz Sawtooth X B-DRY Hikers, Mid
A rugged brown hiker with waterproof B-DRY lining, nubuck leather upper, and reliable multi-directional traction.
(100)
$180 $180
SALE
What customers like:
Snug ankle support
Waterproof protection
Warm and insulated
Sturdy construction
Comfortable fit
$180 $180
SALE
Men's Portland Boots, Chelsea
L.L.Bean Men's Portland Boots, Chelsea
A heritage-inspired leather Chelsea boot with a Vibram® rubber outsole, perfect for city exploration.
(0)
$190 $190
SALE
$190 $190
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, and grippy VertiGrip Trail rubber outsole.
(0)
$140 $140
SALE
$140 $140
SALE
Women's Access Hiking Boots, Waterproof
L.L.Bean Women's Access Hiking Boots, Waterproof
A waterproof hiking boot in deepwater blue with leather/rubber construction and all-day comfort features.
(0)
$150 $150
SALE
$150 $150
SALE

City Hiking Boots

City Hiking Boots bring an outdoor-inspired look to a setting full of familiar streets, neighborhood parks and places still waiting to be discovered. There’s a particular pleasure in seeing a city on foot: noticing the stonework above a doorway, taking the quieter street lined with trees or meeting a friend a few blocks beyond your usual route. When choosing a pair, start with your own preferences rather than someone else’s idea of the right look. Think about whether you like a simple profile or a more substantial silhouette, understated colors or contrasting details, and a boot that sits lower or higher around the ankle. Looking at those differences across the selection can help you narrow the options to styles that feel like a natural part of your wardrobe.

Fit deserves just as much attention as appearance. Check each pair’s size information and any available fit notes, especially if you’re shopping for a style you haven’t worn before. Your usual shoe size is a useful starting point, but it isn’t a substitute for the details provided for an individual boot. When trying boots on, wear the socks you expect to pair with them, lace both boots and take a little time to walk around indoors. Notice how your toes, heels and the tops of your feet feel rather than judging the fit while sitting down. If you use an insert, include it in the try-on, following the boot’s fit guidance. For City Hiking Boots, the most useful comparison is the one grounded in your own feet, your preferences and the information available for each pair—not appearance alone.

Style is often easier to judge when you picture the clothes already hanging by your door. A favorite pair of jeans, straight-leg pants or a familiar jacket can give you a better reference point than an entirely new outfit. Look closely at the shape of the toe, the lacing and the balance of the boot with the pants you wear most often. Those small details can make the difference between a pair you admire and a pair that feels like you. City Hiking Boots can also be a thoughtful gift for someone who enjoys city hiking and appreciates outdoor-inspired style. Before choosing, confirm their size, ask about fit preferences and take a cue from the footwear they already love. A gift chosen around someone’s actual tastes feels personal, whether it marks a birthday, celebrates a move to a new city or simply invites more time outside together.

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