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Casual

Casual

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Chukka subcategory

Chukka

Timberland Men's Emerson Street Mid Lace-Up Sneaker TB0A6BW6EO2 Light Taupe Nubuck Loading Image — Timberland Men's Emerson Street Mid Lace-Up Sneaker TB0A6BW6EO2 Light…

$119.95

Upper made with Premium Timberland LeatherReBOTL fabric liningEVA midsoleRubber outsoleTimberCush Comfort SystemFeel confident on the go with these mid lace-up sneakers made with Premium Timberland Leather and ReBOTL fabric lining containing 50% recycled...

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Timberland Men's Emerson Street Mid Lace-Up Sneaker TB0A6BW6EO2 Light Taupe Nubuck — Timberland Men's Emerson Street Mid Lace-Up Sneaker TB0A6BW6EO2 Light…

$119.95

Upper made with Premium Timberland LeatherReBOTL fabric liningEVA midsoleRubber outsoleTimberCush Comfort SystemFeel confident on the go with these mid lace-up sneakers made with Premium Timberland Leather and ReBOTL fabric lining containing 50% recycled...

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Timberland Men's Emerson Street Mid Lace-Up Sneaker TB0A6BW6EN3 Medium Beige Nubuck Loading Image — Timberland Men's Emerson Street Mid Lace-Up Sneaker TB0A6BW6EN3 Mediu…

$119.95

Upper made with Premium Timberland LeatherReBOTL fabric liningEVA midsoleTimbercush Comfort SystemRubber outsoleFeel confident on the go with these mid lace-up sneakers made with Premium Timberland Leather and ReBOTL fabric lining containing 50% recycled...

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Timberland Men's Emerson Street Mid Lace-Up Sneaker TB0A6BW6EN3 Medium Beige Nubuck — Timberland Men's Emerson Street Mid Lace-Up Sneaker TB0A6BW6EN3 Mediu…

$119.95

Upper made with Premium Timberland LeatherReBOTL fabric liningEVA midsoleTimbercush Comfort SystemRubber outsoleFeel confident on the go with these mid lace-up sneakers made with Premium Timberland Leather and ReBOTL fabric lining containing 50% recycled...

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Timberland Men's Britton Square Mid Lace-Up Boot TB0A6CAAEIZ Rust Suede Loading Image — Timberland Men's Britton Square Mid Lace-Up Boot TB0A6CAAEIZ Rust Sue…

$129.95

Upper made with Premium Timberland LeatherSynthetic liningEVA midsoleTimbercush Comfort SystemDefender Repellent Systems treatmentExperience comfort and durability infused with classic Timberland style. This mid-lace-up Boot has a synthetic lining and an...

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Timberland Men's Britton Square Mid Lace-Up Boot TB0A6CAAEIZ Rust Suede — Timberland Men's Britton Square Mid Lace-Up Boot TB0A6CAAEIZ Rust Sue…

$129.95

Upper made with Premium Timberland LeatherSynthetic liningEVA midsoleTimbercush Comfort SystemDefender Repellent Systems treatmentExperience comfort and durability infused with classic Timberland style. This mid-lace-up Boot has a synthetic lining and an...

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Timberland Men's Euro Hiker TB0A5ZJ5968 Dark Brown Nubuck Loading Image — Timberland Men's Euro Hiker TB0A5ZJ5968 Dark Brown Nubuck

$139.95

$82.00 - $139.95

Upper made with waterproof premium Timberland® leatherLace-up style100% PET lacesReBOTL™ fabric liningEVA footbed and midsoleSteel shank for arch supportOur Euro Hikers are made to tackle uneven terrain with a sole designed for traction and confidence...

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Timberland Men's Euro Hiker TB0A5ZJ5968 Dark Brown Nubuck — Timberland Men's Euro Hiker TB0A5ZJ5968 Dark Brown Nubuck

$139.95

$82.00 - $139.95

Upper made with waterproof premium Timberland® leatherLace-up style100% PET lacesReBOTL™ fabric liningEVA footbed and midsoleSteel shank for arch supportOur Euro Hikers are made to tackle uneven terrain with a sole designed for traction and confidence...

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Timberland Men's Britton Road Mid Lace-Up Waterproof Chukka Boot TB0A69TWEM5 Medium Brown Nubuck Loading Image — Timberland Men's Britton Road Mid Lace-Up Waterproof Chukka Boot TB0A…

$159.95

$92.00 - $159.95

OrthoLite InsolesPremium Timberland LeatherReBOTL MaterialTIMBERGRIPTimberDry Waterproof TechnologyWaterproof Footwear

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Timberland Men's Britton Road Mid Lace-Up Waterproof Chukka Boot TB0A69TWEM5 Medium Brown Nubuck — Timberland Men's Britton Road Mid Lace-Up Waterproof Chukka Boot TB0A…

$159.95

$92.00 - $159.95

OrthoLite InsolesPremium Timberland LeatherReBOTL MaterialTIMBERGRIPTimberDry Waterproof TechnologyWaterproof Footwear

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Timberland Men's Euro Hiker Mid Lace-Up Boot TB0A2P27EIW Burgundy Full Grain Loading Image — Timberland Men's Euro Hiker Mid Lace-Up Boot TB0A2P27EIW Burgundy Ful…

$139.95

$82.00 - $139.95

100% Recycled PETEVAPremium Timberland LeatherPrimaLoft InsulationReBOTL Material

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Timberland Men's Euro Hiker Mid Lace-Up Boot TB0A2P27EIW Burgundy Full Grain — Timberland Men's Euro Hiker Mid Lace-Up Boot TB0A2P27EIW Burgundy Ful…

$139.95

$82.00 - $139.95

100% Recycled PETEVAPremium Timberland LeatherPrimaLoft InsulationReBOTL Material

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Timberland Men's Premium 6 Inch Lace Up Wp Boot TB0A2P6WEJD Medium Orange Full Grain Loading Image — Timberland Men's Premium 6 Inch Lace Up Wp Boot TB0A2P6WEJD Medium Or…

$197.95

$111.53 - $197.95

100% Recycled PETAnti-Fatigue TechnologyPremium Timberland LeatherPrimaLoft InsulationReBOTL MaterialTimberDry Waterproof Technology

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Timberland Men's Premium 6 Inch Lace Up Wp Boot TB0A2P6WEJD Medium Orange Full Grain — Timberland Men's Premium 6 Inch Lace Up Wp Boot TB0A2P6WEJD Medium Or…

$197.95

$111.53 - $197.95

100% Recycled PETAnti-Fatigue TechnologyPremium Timberland LeatherPrimaLoft InsulationReBOTL MaterialTimberDry Waterproof Technology

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Timberland Men's Newmarket Mid Lace Up Chukka Boot TB0A6AZE754 Wheat Nubuck Loading Image — Timberland Men's Newmarket Mid Lace Up Chukka Boot TB0A6AZE754 Wheat …

$139.95

$82.00 - $139.95

OrthoLite InsolesPremium Timberland LeatherReBOTL Material

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Timberland Men's Newmarket Mid Lace Up Chukka Boot TB0A6AZE754 Wheat Nubuck — Timberland Men's Newmarket Mid Lace Up Chukka Boot TB0A6AZE754 Wheat …

$139.95

$82.00 - $139.95

OrthoLite InsolesPremium Timberland LeatherReBOTL Material

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Timberland Men's Britton Road Mid Lace-Up Waterproof Chukka Boot TB0A69TWEM6 Rust Full Grain Loading Image — Timberland Men's Britton Road Mid Lace-Up Waterproof Chukka Boot TB0A…

$159.95

$92.00 - $159.95

OrthoLite InsolesPremium Timberland LeatherReBOTL MaterialTIMBERGRIPTimberDry Waterproof TechnologyWaterproof Footwear

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Timberland Men's Britton Road Mid Lace-Up Waterproof Chukka Boot TB0A69TWEM6 Rust Full Grain — Timberland Men's Britton Road Mid Lace-Up Waterproof Chukka Boot TB0A…

$159.95

$92.00 - $159.95

OrthoLite InsolesPremium Timberland LeatherReBOTL MaterialTIMBERGRIPTimberDry Waterproof TechnologyWaterproof Footwear

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Timberland Men's Motion Scramble Mid Lace Up Wp Hiking Boot TB0A6CENEM4 Medium Brown Full Grain Loading Image — Timberland Men's Motion Scramble Mid Lace Up Wp Hiking Boot TB0A6CENE…

$169.95

$97.00 - $169.95

GreenStridePremium Timberland LeatherReBOTL MaterialRegenerative AgricultureTimberDry Waterproof TechnologyWaterproof Footwear

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Timberland Men's Motion Scramble Mid Lace Up Wp Hiking Boot TB0A6CENEM4 Medium Brown Full Grain — Timberland Men's Motion Scramble Mid Lace Up Wp Hiking Boot TB0A6CENE…

$169.95

$97.00 - $169.95

GreenStridePremium Timberland LeatherReBOTL MaterialRegenerative AgricultureTimberDry Waterproof TechnologyWaterproof Footwear

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Timberland Men's Britton Road Mid Chelsea Boot TB0A6A4WEM5 Medium Brown Nubuck Loading Image — Timberland Men's Britton Road Mid Chelsea Boot TB0A6A4WEM5 Medium Bro…

$149.95

$87.00 - $149.95

EVAPremium Timberland LeatherReBOTL MaterialTIMBERGRIP

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Timberland Men's Britton Road Mid Chelsea Boot TB0A6A4WEM5 Medium Brown Nubuck — Timberland Men's Britton Road Mid Chelsea Boot TB0A6A4WEM5 Medium Bro…

$149.95

$87.00 - $149.95

EVAPremium Timberland LeatherReBOTL MaterialTIMBERGRIP

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Timberland Men's Britton Road 7-Eye Moc Toe Boot TB0A697HEIW Burgundy Full-Grain Loading Image — Timberland Men's Britton Road 7-Eye Moc Toe Boot TB0A697HEIW Burgundy…

$170.00

$97.00 - $170.00

Upper made with Premium Timberland LeatherLace-up styleReBOTL fabric liningOrthoLite Impressions memory foam footbedEVA midsoleTPR weltThe Britton Road 7-Eye Boot brings comfort and elevated heritage-inspired style to your outdoor pursuits, with...

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Timberland Men's Britton Road 7-Eye Moc Toe Boot TB0A697HEIW Burgundy Full-Grain — Timberland Men's Britton Road 7-Eye Moc Toe Boot TB0A697HEIW Burgundy…

$170.00

$97.00 - $170.00

Upper made with Premium Timberland LeatherLace-up styleReBOTL fabric liningOrthoLite Impressions memory foam footbedEVA midsoleTPR weltThe Britton Road 7-Eye Boot brings comfort and elevated heritage-inspired style to your outdoor pursuits, with...

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Timberland Men's Britton Road Mid Lace-Up Waterproof Boot TB0A69UHEN1 Wheat Full-Grain Loading Image — Timberland Men's Britton Road Mid Lace-Up Waterproof Boot TB0A69UHEN1…

$190.00

$148.70 - $190.00

Upper made with waterproof Premium Timberland LeatherLace-up styleReBOTL fabric liningOrthoLite Impressions memory foam footbedEVA midsoleTPR weltDurable, and versatile, with plenty of protection against the elements, the Britton Road Waterproof Boot...

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Timberland Men's Britton Road Mid Lace-Up Waterproof Boot TB0A69UHEN1 Wheat Full-Grain — Timberland Men's Britton Road Mid Lace-Up Waterproof Boot TB0A69UHEN1…

$190.00

$148.70 - $190.00

Upper made with waterproof Premium Timberland LeatherLace-up styleReBOTL fabric liningOrthoLite Impressions memory foam footbedEVA midsoleTPR weltDurable, and versatile, with plenty of protection against the elements, the Britton Road Waterproof Boot...

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Timberland Men's Britton Road Mid Lace-Up Waterproof Boot TB0A69UHEM6 Rust Full-Grain Loading Image — Timberland Men's Britton Road Mid Lace-Up Waterproof Boot TB0A69UHEM6…

$190.00

Upper made with waterproof Premium Timberland LeatherLace-up styleReBOTL fabric liningOrthoLite Impressions memory foam footbedEVA midsoleTPR weltDurable, and versatile, with plenty of protection against the elements, the Britton Road Waterproof Boot...

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Timberland Men's Britton Road Mid Lace-Up Waterproof Boot TB0A69UHEM6 Rust Full-Grain — Timberland Men's Britton Road Mid Lace-Up Waterproof Boot TB0A69UHEM6…

$190.00

Upper made with waterproof Premium Timberland LeatherLace-up styleReBOTL fabric liningOrthoLite Impressions memory foam footbedEVA midsoleTPR weltDurable, and versatile, with plenty of protection against the elements, the Britton Road Waterproof Boot...

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Timberland Men's Newmarket Mid Lace Up Chukka Boot TB0A6AZEEM7 Rust Nubuck Loading Image — Timberland Men's Newmarket Mid Lace Up Chukka Boot TB0A6AZEEM7 Rust N…

$139.95

$82.00 - $139.95

OrthoLite InsolesPremium Timberland LeatherReBOTL Material

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Timberland Men's Newmarket Mid Lace Up Chukka Boot TB0A6AZEEM7 Rust Nubuck — Timberland Men's Newmarket Mid Lace Up Chukka Boot TB0A6AZEEM7 Rust N…

$139.95

$82.00 - $139.95

OrthoLite InsolesPremium Timberland LeatherReBOTL Material

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Timberland Men's Britton Road Mid Lace-Up Waterproof Boot TB0A69UHW02 Black Full-Grain Loading Image — Timberland Men's Britton Road Mid Lace-Up Waterproof Boot TB0A69UHW02…

$190.00

Upper made with waterproof Premium Timberland LeatherLace-up styleReBOTL fabric liningOrthoLite Impressions memory foam footbedEVA midsoleTPR weltDurable, and versatile, with plenty of protection against the elements, the Britton Road Waterproof Boot...

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Timberland Men's Britton Road Mid Lace-Up Waterproof Boot TB0A69UHW02 Black Full-Grain — Timberland Men's Britton Road Mid Lace-Up Waterproof Boot TB0A69UHW02…

$190.00

Upper made with waterproof Premium Timberland LeatherLace-up styleReBOTL fabric liningOrthoLite Impressions memory foam footbedEVA midsoleTPR weltDurable, and versatile, with plenty of protection against the elements, the Britton Road Waterproof Boot...

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Red Wing Heritage Men's Iron Ranger 8078 Alpine Loading Image — Red Wing Heritage Men's Iron Ranger 8078 Alpine

$369.99

Vibram 430 Mini-lugGoodyear Leather Welt and Steel ShankLast 8Full Grain LeatherDull Gilt Hooks and EyeletsFeatures a bump toe that allows toes to move more naturally.The Iron Ranger is an American icon beloved for its standout style and long-lasting...

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Red Wing Heritage Men's Iron Ranger 8078 Alpine — Red Wing Heritage Men's Iron Ranger 8078 Alpine

$369.99

Vibram 430 Mini-lugGoodyear Leather Welt and Steel ShankLast 8Full Grain LeatherDull Gilt Hooks and EyeletsFeatures a bump toe that allows toes to move more naturally.The Iron Ranger is an American icon beloved for its standout style and long-lasting...

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Johnston Murphy Men's Upton Chukka Boot 20-5692 Tan Full Grain Loading Image — Johnston Murphy Men's Upton Chukka Boot 20-5692 Tan Full Grain

$168.95

•Leather and anti-microbial polymesh lining (50% recycled).•Linings are treated with anti-microbial protection for long-lasting wear.•Flexible rubber outsole with TRUFOAM™ for lightweight cushioned comfort.•Removable, molded footbed with m

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Johnston Murphy Men's Upton Chukka Boot 20-5692 Tan Full Grain — Johnston Murphy Men's Upton Chukka Boot 20-5692 Tan Full Grain

$168.95

•Leather and anti-microbial polymesh lining (50% recycled).•Linings are treated with anti-microbial protection for long-lasting wear.•Flexible rubber outsole with TRUFOAM™ for lightweight cushioned comfort.•Removable, molded footbed with m

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Cole Haan Men's Hawthorne Chuk C38728 British Tan - Dark Chocolate W Loading Image — Cole Haan Men's Hawthorne Chuk C38728 British Tan - Dark Chocolate W

$299.95

$75.43 - $299.95

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Timberland Men's Westmore TB0A5YGY901 Canteen Loading Image — Timberland Men's Westmore TB0A5YGY901 Canteen

$129.95

$77.00 - $129.95

Upper made with Premium Timberland Leather100% cotton lacesLace-up stylePolyester liningEVA footbedSensorFlex technologyOur Westmore moc-toe boots elevate your look with the perfect combo of polish and lightweight, athletic style. With 100% cotton laces,...

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Timberland Men's Westmore TB0A5YGY901 Canteen — Timberland Men's Westmore TB0A5YGY901 Canteen

$129.95

$77.00 - $129.95

Upper made with Premium Timberland Leather100% cotton lacesLace-up stylePolyester liningEVA footbedSensorFlex technologyOur Westmore moc-toe boots elevate your look with the perfect combo of polish and lightweight, athletic style. With 100% cotton laces,...

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Casual