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City Walking Shoes

Find city walking shoes for your walks around town, with versatile styles to pair with your everyday wardrobe. Browse the selection and compare individual fit and sizing details to help choose the right pair for you.

Men's HOKA Transport 2 Shoes
HOKA Men's HOKA Transport 2 Shoes
A gray pair of shoes featuring recycled polyester, quick-toggle laces, reflective details, and a recycled outsole.
(0)
$155 $155
SALE
$155 $155
SALE
Men's New Balance 574V3 Walking Shoes
New Balance Men's New Balance 574V3 Walking Shoes
A walking shoe with breathable suede-and-mesh uppers, ENCAP® cushioning, removable foam insoles and rubber outsoles.
(0)
$89.99 $89.99
SALE
$89.99 $89.99
SALE
Men's New Balance 603 Shoes
New Balance Men's New Balance 603 Shoes
A brown walking sneaker with a suede-and-mesh upper, cushioned EVA midsole, and durable rubber outsole.
(0)
$109.99 $109.99
SALE
$109.99 $109.99
SALE
Women's HOKA Transport 2 Shoes
HOKA Women's HOKA Transport 2 Shoes
A white polyester athleisure shoe with city-to-trail versatility, reflective details, water-repellent finish, and recycled materials.
(0)
$155 $155
SALE
$155 $155
SALE
Women's New Balance 574V3 Walking Shoes
New Balance Women's New Balance 574V3 Walking Shoes
A blue suede-and-mesh walking shoe with ENCAP support, removable foam insole, and durable rubber outsole.
(95)
$89.99 $89.99
SALE
$89.99 $89.99
SALE
Men's Comfort Walkers 2, Ventilated
L.L.Bean Men's Comfort Walkers 2, Ventilated
A gray walking shoe with water-resistant suede, breathable mesh, reflective overlays and cushioned, supportive traction.
(0)
$110 $110
SALE
$110 $110
SALE
Women's Comfort Walkers 2, Ventilated
L.L.Bean Women's Comfort Walkers 2, Ventilated
A gray walking shoe with water-resistant suede, mesh panels, reflective overlays and cushioned, stable rubber traction.
(0)
$110 $110
SALE
$110 $110
SALE
Women's VEJA Campo Sneakers, Bold
Veja Women's VEJA Campo Sneakers, Bold
A tan leather sneaker with recycled, plant-based materials, organic cotton laces, and clean minimalist styling.
(0)
$160 $160
SALE
$160 $160
SALE
Men's On Cloud 6 Shoes
On Men's On Cloud 6 Shoes
A blue sneaker with breathable recycled-polyester mesh, CloudTec cushioning, Speedboard support, and a durable rubber outsole.
(0)
$150 $150
SALE
$150 $150
SALE
Men's Elevation Everyday Slip-Ons, Leather
L.L.Bean Men's Elevation Everyday Slip-Ons, Leather
Brown leather slip-on shoes with water-resistant uppers, cushioned midsoles, and grippy rubber outsoles for all-day comfort.
(0)
$110 $110
SALE
$110 $110
SALE
Women's Bean's Comfort Fitness Walking Shoes, Waterproof
L.L.Bean Women's Bean's Comfort Fitness Walking Shoes, Waterproof
A gray waterproof walking shoe with breathable mesh, cushioned support, and grippy rubber traction.
(276)
$120 $84.99
SALE
What customers like:
Supportive
Waterproof
Versatile
Comfortable
Well made
$120 $84.99
SALE
Men's New Balance 300 Court Shoes
New Balance Men's New Balance 300 Court Shoes
A yellow court-inspired sneaker with split suede-and-mesh upper, cushioned insole and durable rubber outsole.
(0)
$89.99 $89.99
SALE
$89.99 $89.99
SALE
Men's New Balance 990V6 Running Shoes
New Balance Men's New Balance 990V6 Running Shoes
A multicolor leather-and-mesh running-inspired sneaker with ENCAP stability, plush cushioning, and a durable rubber outsole.
(0)
$199.95 $199.95
SALE
$199.95 $199.95
SALE
Men's Portland Boots, Chelsea
L.L.Bean Men's Portland Boots, Chelsea
A red leather Chelsea boot with elastic gores and a lightweight lugged Vibram rubber outsole.
(0)
$190 $190
SALE
$190 $190
SALE
Men's Portland Boots, Lace-Up
L.L.Bean Men's Portland Boots, Lace-Up
A red leather lace-up boot with D-rings, speed hooks, and a lightweight lugged Vibram rubber outsole.
(0)
$200 $200
SALE
$200 $200
SALE
Men's NextVenture Waterproof Slip-On Shoes, Suede
L.L.Bean Men's NextVenture Waterproof Slip-On Shoes, Suede
A brown waterproof suede slip-on shoe with cushioned EVA comfort and grippy rubber traction.
(0)
$150 $150
SALE
$150 $150
SALE
Women's Double L Sneakers, Lace Up
L.L.Bean Women's Double L Sneakers, Lace Up
A black leather sneaker with cushioned comfort, supportive rubber cupsole, and mini-lug traction for everyday adventures.
(0)
$99 $49.99
SALE
$99 $49.99
SALE
Men's Keen Jasper Zionic Sneakers
Keen Men's Keen Jasper Zionic Sneakers
A green leather-and-rubber sneaker with lightweight hiker comfort, breathable lining, and high-traction lugs.
(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 tan waterproof leather slip-on shoe with cushioned EVA midsole and grippy Vibram outsole for trails.
(0)
$150 $150
SALE
$150 $150
SALE
Women's Camden Hills Penny Loafers, Leather
L.L.Bean Women's Camden Hills Penny Loafers, Leather
A brown leather penny loafer with cushioned comfort, supportive design, and durable mini-lug rubber traction.
(0)
$140 $99.99
SALE
$140 $99.99
SALE
Men's Bucksport Shoes, Plain Toe
L.L.Bean Men's Bucksport Shoes, Plain Toe
A brown waterproof oiled-leather shoe with Vibram® lugged soles, triple-needle stitching, and all-day comfort.
(835)
$170 $170
SALE
What customers like:
Excellent quality
Durable
Great appearance
Versatile
Comfortable
$170 $170
SALE
Women's Camden Hills Boots, Lace-Up
L.L.Bean Women's Camden Hills Boots, Lace-Up
A black full-grain leather lace-up boot with a cushioned footbed and grippy mini-lug rubber outsole.
(0)
$190 $129.99
SALE
$190 $129.99
SALE
Women's Camden Hills Chelsea Boots
L.L.Bean Women's Camden Hills Chelsea Boots
Chelsea boots in brown full-grain leather feature stretchy side gores, cushioned footbeds, and rugged mini-lug traction.
(0)
$190 $84.99
SALE
$190 $84.99
SALE
Men's 1985 Mountain Classic Sneakers
L.L.Bean Men's 1985 Mountain Classic Sneakers
A black suede-and-nylon sneaker with cushioned B-Bound® midsole, thermoregulating lining, and grippy VertiGrip outsole.
(0)
$110 $64.99
SALE
$110 $64.99
SALE

City Walking Shoes

City Walking Shoes are part of the everyday rhythm of getting outside: passing the neighborhood bakery as the door opens, taking the long way around a favorite block, and noticing a mural you’ve walked past a dozen times before. Choosing a pair starts with your own sense of style and the city walking you enjoy. You might prefer a simple, understated shape that looks familiar alongside your favorite jeans, or a sportier design that adds a casual touch to an otherwise classic outfit. Consider the proportions as well as the color: a substantial silhouette creates a different look from a streamlined one, even when both are worn with the same pants. This collection offers a place to compare those details and find a style that feels like you. Rather than choosing around a single outfit, think about the clothes you reach for most often and the shoes you can picture beside them.

Fit deserves a closer look before you settle on a pair. Start with the individual listing’s size information, available widths, and any guidance about how the style runs; your usual size is a starting point, not a reason to skip the details. When trying shoes on, wear the socks you expect to wear with them, check both feet, and take a few steps to notice whether your toes have room and your heels stay in place. Pay attention to any pinching or slipping rather than assuming it will disappear with wear. Beyond fit, look closely at the opening, closure, and overall shape. Think about whether you like adjusting laces or prefer a different style of entry, and review the care instructions so you know what upkeep involves. Comparing these particulars can be more helpful than choosing by appearance alone, especially when two pairs look similar at first glance.

For someone who enjoys city walking, a thoughtfully chosen pair can also make a personal gift. Picture the person’s existing wardrobe and favorite shoes before deciding: the friend who keeps everything understated may appreciate a quieter design, while someone who enjoys color may welcome a more noticeable accent. Confirm their size and width preferences when possible, and check the exchange options rather than guessing about fit. The same attention is worthwhile when shopping for yourself. Think of a familiar Saturday spent wandering blocks with a friend, pausing to admire a window display, or catching up on the walk through your neighborhood. Those ordinary moments provide a useful starting point for choosing a style—not an imagined occasion that rarely comes around, but the city walking that’s already part of your life. Look for a pair whose appearance, fit, and details suit your preferences, and make the choice your own.

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