Skip to main content
{count} Cart

Free 3-day shipping - free returns

[ES_CATEGORY_TOP_HERO]

MEN'S CHUKKAS

Men's chukka boots have been in style for more than a century, starting as desert boots and evolving throughout the 1900s into much more than just standard men's leather boots. Their distinctive mid height and versatility in material and style makes our chukkas some of our most popular footwear styles.

Back To Top
Women's Nature Needs Heroes Nellie Chukka Boots
[ES_PRODUCT_GRID_PROMOTION_MESSAGE]
EXTRA 25% OFF- IN CART
Women's Nature Needs Heroes Nellie Chukka Boots
$140.00 $109.99

21% off

Men's Adventure Modern Chukka Shoes
Black Nubuck
Light Grey Nubuck
Beige Nubuck
Medium Grey Nubuck
[ES_PRODUCT_GRID_PROMOTION_MESSAGE]
EXTRA 25% OFF- IN CART
Men's Adventure Modern Chukka Shoes
$120.00 $99.99

17% off

Men's Kendrick Waterproof Chukka Boots
Dark Brown Full-Grain
Black Full-Grain
[ES_PRODUCT_GRID_PROMOTION_MESSAGE]
Men's Kendrick Waterproof Chukka Boots
$160.00
Men's Groveton Chukka Shoes
Dark Grey Nubuck
Grey Nubuck
Black Nubuck/Canvas
Dark Green Nubuck
Black Camo Nubuck
Green Camo Nubuck
Beige Camo Nubuck
Navy Nubuck/Canvas
Black Nubuck/Canvas
[ES_PRODUCT_GRID_PROMOTION_MESSAGE]
Men's Groveton Chukka Shoes
$80.00
Men's Killington Chukka Sneaker Boots
[ES_PRODUCT_GRID_PROMOTION_MESSAGE]
Men's Killington Chukka Sneaker Boots
$125.00
Men's Timberland® Waterproof Chukka Boots
Wheat Nubuck
Black Smooth
[ES_PRODUCT_GRID_PROMOTION_MESSAGE]
Men's Timberland® Waterproof Chukka Boots
$135.00
Men's Folk Gentleman Chukka Boots
Dark Brown Suede
Dark Blue Suede
Rust Suede
[ES_PRODUCT_GRID_PROMOTION_MESSAGE]
EXTRA 25% OFF- IN CART
Men's Folk Gentleman Chukka Boots
$110.00
Men's Timberland® Waterproof Chukka Boots
GORE-TEX®
[ES_PRODUCT_GRID_PROMOTION_MESSAGE]
Men's Timberland® Waterproof Chukka Boots
$155.00
Men's Groveton Leather Chukka Shoes
Brown Full-Grain
Black Full-Grain
Grey Full-Grain
[ES_PRODUCT_GRID_PROMOTION_MESSAGE]
Men's Groveton Leather Chukka Shoes
$100.00
Men's Groveton Chukka Shoes
Black Nubuck/Canvas
Grey Nubuck
Dark Grey Nubuck
Dark Green Nubuck
Black Camo Nubuck
Green Camo Nubuck
Beige Camo Nubuck
Navy Nubuck/Canvas
Black Nubuck/Canvas
[ES_PRODUCT_GRID_PROMOTION_MESSAGE]
Men's Groveton Chukka Shoes
$80.00
Men's Groveton Chukka Shoes
Black Nubuck/Canvas
Grey Nubuck
Black Nubuck/Canvas
Dark Grey Nubuck
Dark Green Nubuck
Black Camo Nubuck
Green Camo Nubuck
Beige Camo Nubuck
Navy Nubuck/Canvas
[ES_PRODUCT_GRID_PROMOTION_MESSAGE]
Men's Groveton Chukka Shoes
$80.00
Men's Adventure Cupsole Chukka Shoes
Burnished Wheat Nubuck
Olive Full-Grain
Medium Brown Full-Grain
[ES_PRODUCT_GRID_PROMOTION_MESSAGE]
Men's Adventure Cupsole Chukka Shoes
$110.00
Men's Timberland® Waterproof Chukka Boots
Black Smooth
Wheat Nubuck
[ES_PRODUCT_GRID_PROMOTION_MESSAGE]
Men's Timberland® Waterproof Chukka Boots
$135.00
Men's Squall Canyon Waterproof Chukka Boots
Waterproof
[ES_PRODUCT_GRID_PROMOTION_MESSAGE]
Men's Squall Canyon Waterproof Chukka Boots
$150.00
Men's Folk Gentleman Chukka Boots
Rust Suede
Dark Blue Suede
Dark Brown Suede
[ES_PRODUCT_GRID_PROMOTION_MESSAGE]
EXTRA 25% OFF- IN CART
Men's Folk Gentleman Chukka Boots
$110.00
Men's Adventure Modern Chukka Shoes
Beige Nubuck
Black Nubuck
Light Grey Nubuck
Medium Grey Nubuck
[ES_PRODUCT_GRID_PROMOTION_MESSAGE]
EXTRA 25% OFF- IN CART
Men's Adventure Modern Chukka Shoes
$120.00 $99.99

17% off

Men's Timberland® Icon Waterproof Chukka Boots
[ES_PRODUCT_GRID_PROMOTION_MESSAGE]
Men's Timberland® Icon Waterproof Chukka Boots
$145.00
Men's FlyRoam™ Go Chukka Sneakers
Black Full-Grain/Mesh
Grey Full-Grain/Mesh
[ES_PRODUCT_GRID_PROMOTION_MESSAGE]
EXTRA 25% OFF- IN CART
Men's FlyRoam™ Go Chukka Sneakers
$120.00
Men's Groveton Leather Chukka Shoes
Black Full-Grain
Grey Full-Grain
Brown Full-Grain
[ES_PRODUCT_GRID_PROMOTION_MESSAGE]
Men's Groveton Leather Chukka Shoes
$100.00
Men's Groveton Leather Chukka Shoes
Grey Full-Grain
Black Full-Grain
Brown Full-Grain
[ES_PRODUCT_GRID_PROMOTION_MESSAGE]
Men's Groveton Leather Chukka Shoes
$100.00
Men's Kendrick Waterproof Chukka Boots
Black Full-Grain
Dark Brown Full-Grain
[ES_PRODUCT_GRID_PROMOTION_MESSAGE]
Men's Kendrick Waterproof Chukka Boots
$160.00
Men's City's Edge Waterproof Chukka Boots
Dark Brown Full-Grain
Black Full-Grain
GORE-TEX®
[ES_PRODUCT_GRID_PROMOTION_MESSAGE]
Men's City's Edge Waterproof Chukka Boots
$160.00
Men's Timberland® Classic Waterproof Chukka Boots
[ES_PRODUCT_GRID_PROMOTION_MESSAGE]
Men's Timberland® Classic Waterproof Chukka Boots
$145.00
Men's Bradstreet Leather Chukka Sneaker Boots
Grey Nubuck
Dark Blue Nubuck
Green Nubuck
Black Nubuck
Wheat Nubuck
[ES_PRODUCT_GRID_PROMOTION_MESSAGE]
Men's Bradstreet Leather Chukka Sneaker Boots
$120.00
Load More
[ES_PRODUCT_GRID_SPLIT_RECOMMENDATION_1]

MEN'S CHUKKA BOOTS

Timberland® men's chukkas have become some of our most popular footwear. Try a pair of our men's chukka boots for the ultimate smooth ride and a modern look that blends athletic styling with heritage details. Versatility comes standard: Our Timberland® chukka boots work for everything from casual Fridays to date nights.

[ES_PRODUCT_GRID_SPLIT_RECOMMENDATION_2]
[ES_FOOTER_CONTENT_3]