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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 Heritage Hiking Boots, Waterproof
L.L.Bean Men's Heritage Hiking Boots, Waterproof
A gray waterproof suede-and-nylon hiking boot with cushioned support and grippy traction for trails and town.
(0)
$150 $109.99
SALE
$150 $109.99
SALE
Men's NextVenture Boots, Lace-Up
L.L.Bean Men's NextVenture Boots, Lace-Up
A tan leather-and-rubber waterproof boot with cushioned support and Vibram® traction for town and trail.
(0)
$170 $170
SALE
$170 $170
SALE
Women's NextVenture Boots, Lace-Up
L.L.Bean Women's NextVenture Boots, Lace-Up
A gray waterproof rubber lace-up boot with EVA comfort, thermoregulating lining, and Vibram traction for trails.
(0)
$170 $109.99
SALE
$170 $109.99
SALE
Men's Keen Targhee IV Mid Waterproof Hiking Boots
Keen Men's Keen Targhee IV Mid Waterproof Hiking Boots
A multicolor waterproof hiking boot with nubuck leather and mesh, supportive cushioning, and grippy non-marking lugs.
(0)
$180 $180
SALE
$180 $180
SALE
Men's Portland Boots, Lace-Up
L.L.Bean Men's Portland Boots, Lace-Up
A red leather boot with speed hooks and a lightweight lugged rubber outsole for durable traction.
(0)
$200 $200
SALE
$200 $200
SALE
Women's NextVenture Boots, Chelsea
L.L.Bean Women's NextVenture Boots, Chelsea
A tan waterproof Chelsea boot with oiled nubuck uppers and Vibram® traction for town-to-trail adventures.
(0)
$150 $99.99
SALE
$150 $99.99
SALE
Men's NextVenture Boots, Chelsea
L.L.Bean Men's NextVenture Boots, Chelsea
A tan waterproof Chelsea boot with oiled nubuck, cushioned comfort, and rugged traction for town-to-trail adventures.
(0)
$150 $150
SALE
$150 $150
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 B-DRY lining, nubuck leather, supportive cushioning, and multidirectional traction.
(93)
$200 $200
SALE
What customers like:
Durable quality
Great support
High comfort
Excellent fitting
Reliable traction
$200 $200
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 construction, cushioned comfort, and reliable Vibram® traction.
(0)
$150 $150
SALE
$150 $150
SALE
Women's Keen Targhee IV Mid Waterproof Hiking Boots
Keen Women's Keen Targhee IV Mid Waterproof Hiking Boots
A brown leather hiking boot with waterproof protection, lightweight stability, cushioned comfort, and multi-directional traction.
(0)
$180 $180
SALE
$180 $180
SALE
Women's Oboz Bridger Mid B-Dry Hiking Boots
Oboz Women's Oboz Bridger Mid B-Dry Hiking Boots
A gray waterproof nubuck leather hiking boot with breathable membrane, supportive cushioning, and grippy rubber tread.
(0)
$200 $200
SALE
$200 $200
SALE
Men's Heritage Hiking Shoes, Waterproof
L.L.Bean Men's Heritage Hiking Shoes, Waterproof
A gray waterproof hiking shoe with a suede-and-nylon upper, cushioned insole, and grippy rubber outsole.
(0)
$140 $99.99
SALE
$140 $99.99
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 grippy rubber traction for trails.
(181)
$220 $220
SALE
What customers like:
Light
Sturdy
Comfortable
Good quality orthotic base
Looks great
$220 $220
SALE
Men's Trail Model X Waterproof Hiking Boots, Leather
L.L.Bean Men's Trail Model X Waterproof Hiking Boots, Leather
A brown leather hiking boot with waterproof protection, enhanced wet-surface traction, EVA cushioning and protective toe.
(0)
$130 $130
SALE
$130 $130
SALE
Women's Oboz Sawtooth X B-DRY Hikers, Mid
Oboz Women's Oboz Sawtooth X B-DRY Hikers, Mid
A brown mid hiking boot with waterproof protection, nubuck leather, supportive cushioning, and reliable wet-trail traction.
(100)
$200 $200
SALE
What customers like:
Warmth
Snug ankle support
Sturdy construction
Comfortable fit
$200 $200
SALE
Women's NextVenture Hiking Shoes, Waterproof
L.L.Bean Women's NextVenture Hiking Shoes, Waterproof
A brown waterproof hiking shoe with mesh, leather and rubber construction, cushioned comfort and trail traction.
(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 hiking boot with waterproof protection, wet-surface traction, rubber toe protection and cushioning.
(0)
$120 $120
SALE
$120 $120
SALE
Women's Trail Model X Waterproof Hiking Boots
L.L.Bean Women's Trail Model X Waterproof Hiking Boots
A tan waterproof hiking boot with suede upper, rubberized toe, cushioned EVA midsole and wet-surface traction.
(0)
$120 $120
SALE
$120 $120
SALE
Women's Trail Model X Waterproof Hiking Boots, Leather
L.L.Bean Women's Trail Model X Waterproof Hiking Boots, Leather
A gray waterproof leather hiking boot with a thermoregulating lining, rock plate, and grippy rubber outsole.
(0)
$130 $130
SALE
$130 $130
SALE
Men's Keen Targhee IV Waterproof Hiking Shoes
Keen Men's Keen Targhee IV Waterproof Hiking Shoes
A waterproof, multicolor nubuck leather hiker offering supportive stability, cushioned comfort, and confident all-terrain traction.
(0)
$170 $170
SALE
$170 $170
SALE
Women's Camden Hills Alpine Boots
L.L.Bean Women's Camden Hills Alpine Boots
A brown leather alpine boot with wool lining, side zipper, and rugged rubber traction for exploration.
(0)
$180 $119.99
SALE
$180 $119.99
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 protection, cushioned comfort, and Vibram rubber traction.
(0)
$280 $280
SALE
$280 $280
SALE
Men's Access Hiking Boots, Waterproof
L.L.Bean Men's Access Hiking Boots, Waterproof
A blue leather-and-rubber hiking boot with waterproof protection, grippy traction and cushioned, supportive comfort.
(0)
$150 $126.99
SALE
$150 $126.99
SALE
Men's Portland Boots, Chelsea
L.L.Bean Men's Portland Boots, Chelsea
A red leather pull-on boot with elastic goring and a lightweight lugged Vibram rubber outsole.
(0)
$190 $190
SALE
$190 $190
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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