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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 Redwood Falls Waterproof Moc-Toe Boot TB1A2EDRF13 Rust Full-Grain Loading Image — Timberland Men's Redwood Falls Waterproof Moc-Toe Boot TB1A2EDRF13 Ru…

$160.00

$128.00

Upper made with waterproof Premium Timberland LeatherRustproof speed lace hardware with lace hooks at topReBOTL fabric liningOrthoLite footbedEVA midsoleSteel shank for arch supportThese men's boots are built to hit the trail in comfort, with a cushioned...

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Timberland Men's Redwood Falls Waterproof Moc-Toe Boot TB1A2EDRF13 Rust Full-Grain — Timberland Men's Redwood Falls Waterproof Moc-Toe Boot TB1A2EDRF13 Ru…

$160.00

$128.00

Upper made with waterproof Premium Timberland LeatherRustproof speed lace hardware with lace hooks at topReBOTL fabric liningOrthoLite footbedEVA midsoleSteel shank for arch supportThese men's boots are built to hit the trail in comfort, with a cushioned...

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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

$142.75 - $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

$142.75 - $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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Casual