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    • Sale
      City Groove Chukka for Men in Dark Brown Timberland On SaleCity Groove Chukka for Men in Dark Brown Timberland On Sale

      City Groove Chukka for Men in Dark Brown Timberland On Sale

      This men's chukka is made with premium Better Leather sourced from a sustainable tannery rated silver for its environmental processes. The chukka has a foam footbed for cushioning, and the laces are made with 50% recycled PET. The rubber heel and outsole provide durability...
      $43.00
      $130.50
      $43.00
      Unit price
      / per 
      • Dark Brown
    • Sale
      City Groove Chelsea Boot for Men in Dark Brown Timberland For SaleCity Groove Chelsea Boot for Men in Dark Brown Timberland For Sale

      City Groove Chelsea Boot for Men in Dark Brown Timberland For Sale

      A pull-on tab and dual stretch gore make our City Groove men's Chelsea boots easy to put on, while the rubber heel and outsole offer traction on everything from slick floors to sidewalks and trails. This style also features a comfy cushioned footbed and...
      $46.00
      $139.59
      $46.00
      Unit price
      / per 
      • Dark Brown
    • Sale
      City Groove Chukka for Men in Black Timberland OutletCity Groove Chukka for Men in Black Timberland Outlet

      City Groove Chukka for Men in Black Timberland Outlet

      This men's chukka is made with premium Better Leather sourced from a sustainable tannery rated silver for its environmental processes. The chukka has a foam footbed for cushioning, and the laces are made with 50% recycled PET. The rubber heel and outsole provide durability...
      $42.99
      $130.00
      $42.99
      Unit price
      / per 
      • Black
    • Sale
      Sprint Trekker Chukka for Men in Yellow Timberland OnlineSprint Trekker Chukka for Men in Yellow Timberland Online

      Sprint Trekker Chukka for Men in Yellow Timberland Online

      This men's chukka has our exclusive TimberDry™ waterproof lining made of 50% recycled plastic , to help keep feet dry wherever you're heading. The chukka is crafted with an upper and lining in durable ReBOTL™ fabric mesh, which also contains at least 50% recycled...
      $37.50
      $113.59
      $37.50
      Unit price
      / per 
      • Yellow
    • Sale
      Alden Brook Side-Zip Boot for Men in Dark Brown Timberland SaleAlden Brook Side-Zip Boot for Men in Dark Brown Timberland Sale

      Alden Brook Side-Zip Boot for Men in Dark Brown Timberland Sale

      Constructed with a cushioned interior and built-in arch support, this Alden Brook men's traditional lace-up boot has a convenient side zip for easy on/off. Plus, it's fully waterproofed with our exclusive TimberDry™ membrane made of 50% recycled plastic bottles. The leather and linings were...
      $45.50
      $151.00
      $45.50
      Unit price
      / per 
      • Dark Brown
    • Sale
      Alden Brook Side-Zip Boot for Men in Brown Timberland DiscountAlden Brook Side-Zip Boot for Men in Brown Timberland Discount

      Alden Brook Side-Zip Boot for Men in Brown Timberland Discount

      Constructed with a cushioned interior and built-in arch support, this Alden Brook men's traditional lace-up boot has a convenient side zip for easy on/off. Plus, it's fully waterproofed with our exclusive TimberDry™ membrane made of 50% recycled plastic bottles. The leather and linings were...
      $45.50
      $151.50
      $45.50
      Unit price
      / per 
      • Brown
    • Sale
      Stormbucks Chelsea Boot for Men in Dark Brown Timberland USStormbucks Chelsea Boot for Men in Dark Brown Timberland US

      Stormbucks Chelsea Boot for Men in Dark Brown Timberland US

      The convenience of a pull-on Chelsea style meets the warm lining you need for winter in these men's leather boots. Environmentally sensitive materials such as responsibly sourced leather and an eco-conscious lining feel good in any season.CARE INSTRUCTIONS:CleanerBoot Sauce™ CleanerRubber Sole BrushMax® Shoe ShineMade...
      $40.99
      $136.50
      $40.99
      Unit price
      / per 
      • Dark Brown
    • Sale
      Stormbucks Chelsea Boot for Men in Light Brown Timberland On SaleStormbucks Chelsea Boot for Men in Light Brown Timberland On Sale

      Stormbucks Chelsea Boot for Men in Light Brown Timberland On Sale

      The convenience of a pull-on Chelsea style meets the warm lining you need for winter in these men's leather boots. Environmentally sensitive materials such as responsibly sourced leather and an eco-conscious lining feel good in any season.CARE INSTRUCTIONS:CleanerBoot Sauce™ CleanerRubber Sole BrushMax® Shoe ShineMade...
      $41.00
      $136.59
      $41.00
      Unit price
      / per 
      • Light Brown
    • Sale
      Bradstreet Chukka for Men in Dark Brown Timberland For SaleBradstreet Chukka for Men in Dark Brown Timberland For Sale

      Bradstreet Chukka for Men in Dark Brown Timberland For Sale

      This casual and comfortable men's chukka has an upper in premium Better Leather, which is sourced from a sustainable tannery rated silver for its environmental processes. The durable lining uses ReBOTL™ fabric, containing at least 50% recycled plastic. This chukka features a three-layer SensorFlex™...
      $37.50
      $113.59
      $37.50
      Unit price
      / per 
      • Dark Brown
    • Sale
      Larchmont II Mid Chukka for Men in Grey Timberland OutletLarchmont II Mid Chukka for Men in Grey Timberland Outlet

      Larchmont II Mid Chukka for Men in Grey Timberland Outlet

      This men’s lace-up chukka features Gripstick™ rubber and our exclusive multi-directional Traction Lug technology for superior traction on the move. This chukka is responsibly made using premium Better Leather sourced from a sustainable tannery rated silver for its environmental processes, and ReBOTL™ fabric lining...
      $39.50
      $119.50
      $39.50
      Unit price
      / per 
      • Grey
    • Sale
      Cross Mark Chukka for Men in Dark Brown Timberland OnlineCross Mark Chukka for Men in Dark Brown Timberland Online

      Cross Mark Chukka for Men in Dark Brown Timberland Online

      This men's plain-toe chukka is responsibly-made with premium Better Leather from a sustainable tannery rated silver for its environmental processes, while the eco-conscious ReBOTL™ fabric lining contains at least 50% recycled plastic.CARE INSTRUCTIONS:CleanerRenewbuck® Suede and Nubuck Foam CleanerSuede Restorer BrushDry Cleaning KitProtectorBalm Proofer™ All...
      $44.99
      $135.99
      $44.99
      Unit price
      / per 
      • Dark Brown
    • Sale
      Newmarket II 6 Inch Moc-toe Boot for Men in Brown Timberland SaleNewmarket II 6 Inch Moc-toe Boot for Men in Brown Timberland Sale

      Newmarket II 6 Inch Moc-toe Boot for Men in Brown Timberland Sale

      This men's 6-inch moc-toe boot is made with premium Better Leather sourced from a sustainable tannery rated silver for its environmental processes. The durable ReBOTL™ fabric lining also contains at least 50% recycled plastic. This boot has a rugged but classic style, and is...
      $42.99
      $142.59
      $42.99
      Unit price
      / per 
      • Brown
    • Sale
      Bradstreet Ultra Chukka Boot for Men in Brown Timberland DiscountBradstreet Ultra Chukka Boot for Men in Brown Timberland Discount

      Bradstreet Ultra Chukka Boot for Men in Brown Timberland Discount

      Our Bradstreet Ultra leather chukkas for men class up any look, while also helping to protect the planet. They are fitted with our new eco-conscious GreenStride™ comfort soles made with renewable sugar cane and responsibly sourced rubber, as well as being constructed from Better...
      $39.99
      $121.00
      $39.99
      Unit price
      / per 
      • Brown
    • Sale
      Bradstreet Ultra Chukka Boot for Men in Monochrome Black Timberland USBradstreet Ultra Chukka Boot for Men in Monochrome Black Timberland US

      Bradstreet Ultra Chukka Boot for Men in Monochrome Black Timberland US

      Our Bradstreet Ultra leather chukkas for men class up any look, while also helping to protect the planet. They are fitted with our new eco-conscious GreenStride™ comfort soles made with renewable sugar cane and responsibly sourced rubber, as well as being constructed from Better...
      $39.59
      $120.50
      $39.59
      Unit price
      / per 
      • Monochrome Black
    • Sale
      Bee Line x Timberland® 6 Inch Rubber Toe Boot for Men in Dark Green Timberland For SaleBee Line x Timberland® 6 Inch Rubber Toe Boot for Men in Dark Green Timberland For Sale

      Bee Line x Timberland® 6 Inch Rubber Toe Boot for Men in Dark Green Timberland For Sale

      When you think of Timberland® boots, you're thinking of these. Our original waterproof boot was designed more than 40 years ago and remains a best-seller today, with tireless waterproof performance and instantly recognisable work-boot styling. This style features an anti-fatigue removable footbed for all-day...
      $59.99
      $199.59
      $59.99
      Unit price
      / per 
      • Dark Green
    • Sale
      Bee Line x Timberland® 6 Inch Rubber Toe Boot for Men in Dark Green/Orange Timberland On SaleBee Line x Timberland® 6 Inch Rubber Toe Boot for Men in Dark Green/Orange Timberland On Sale

      Bee Line x Timberland® 6 Inch Rubber Toe Boot for Men in Dark Green/Orange Timberland On Sale

      When you think of Timberland® boots, you're thinking of these. Our original waterproof boot was designed more than 40 years ago and remains a best-seller today, with tireless waterproof performance and instantly recognisable work-boot styling. This style features an anti-fatigue removable footbed for all-day...
      $59.59
      $199.50
      $59.59
      Unit price
      / per 
      • Dark Green
    • Sale
      Timberland® Premium Extra Warm 6 Inch Boot for Men in Brown Timberland OutletTimberland® Premium Extra Warm 6 Inch Boot for Men in Brown Timberland Outlet

      Timberland® Premium Extra Warm 6 Inch Boot for Men in Brown Timberland Outlet

      This men's waterproof winter boot is inspired by our original Timberland® boot, and is made with premium Better Leather sourced from a sustainable tannery rated silver for its environmental processes. This instantly recognisable work-boot style gives you lasting waterproof performance and also features PrimaLoft®...
      $49.50
      $164.00
      $49.50
      Unit price
      / per 
      • Brown
    • Sale
      Timberland® Premium Extra Warm 6 Inch Boot for Men in Yellow Full Grain Timberland OnlineTimberland® Premium Extra Warm 6 Inch Boot for Men in Yellow Full Grain Timberland Online

      Timberland® Premium Extra Warm 6 Inch Boot for Men in Yellow Full Grain Timberland Online

      This men's waterproof winter boot is inspired by our original Timberland® boot, and is made with premium Better Leather sourced from a sustainable tannery rated silver for its environmental processes. This instantly recognisable work-boot style gives you lasting waterproof performance and also features PrimaLoft®...
      $49.50
      $164.50
      $49.50
      Unit price
      / per 
      • Yellow
    • Sale
      Timberland® Euro Hiker Hiking Boot for Men in Black Timberland DiscountTimberland® Euro Hiker Hiking Boot for Men in Black Timberland Discount

      Timberland® Euro Hiker Hiking Boot for Men in Black Timberland Discount

      The Euro Hiker has been a favourite for many years, due to its good looks and superior comfort. Enjoy cushiony EVA midsoles, strong arch support, and outsoles built for traction. These men's mixed-media boots also feature eco-consciously sourced leather, fabric, and laces.CARE INSTRUCTIONS:CleanerRenewbuck® Suede...
      $38.00
      $115.00
      $38.00
      Unit price
      / per 
      • Black
    • Sale
      Bradstreet Ultra Gore-Tex® Chukka for Men in Brown Timberland SaleBradstreet Ultra Gore-Tex® Chukka for Men in Brown Timberland Sale

      Bradstreet Ultra Gore-Tex® Chukka for Men in Brown Timberland Sale

      Take on the elements in these men's leather chukkas with Gore-Tex® bootie construction for complete waterproof protection. They also feel good on your feet - and let you feel good about helping to protect the environment, with eco-conscious laces and our GreenStride™ soles made...
      $41.00
      $136.99
      $41.00
      Unit price
      / per 
      • Brown
    • Sale
      Field Trekker Chukka for Men in Black Timberland USField Trekker Chukka for Men in Black Timberland US

      Field Trekker Chukka for Men in Black Timberland US

      This men's chukka is built for comfort with a lightweight Ortholite® footbed and EVA-blend foam midsole. The chukka is also made with eco-conscious materials, including ReBOTL™ fabric containing at least 50% recycled plastic. Durable Helcor® Leather adds protection.CARE INSTRUCTIONS:CleanerBoot Sauce™ CleanerRubber Sole BrushMax® Shoe...
      $39.50
      $109.00
      $39.50
      Unit price
      / per 
      • Black
    • Sale
      Sprint Trekker Chukka for Men in Black Timberland On SaleSprint Trekker Chukka for Men in Black Timberland On Sale

      Sprint Trekker Chukka for Men in Black Timberland On Sale

      This men's chukka is made with premium Better Leather sourced from a sustainable tannery rated silver for its environmental processes. The detailing on the upper and the interior lining are both made with durable ReBOTL™ fabric made with at least 50% recycled plastic. The...
      $39.99
      $110.59
      $39.99
      Unit price
      / per 
      • Black
    • Sale
      Plymouth Gore-Tex® Trail Hiker for Men in Brown Timberland For SalePlymouth Gore-Tex® Trail Hiker for Men in Brown Timberland For Sale

      Plymouth Gore-Tex® Trail Hiker for Men in Brown Timberland For Sale

      Our men's Plymouth Trail waterproof hiking boot is crafted from premium Better Leather sourced from a sustainable tannery rated silver for its environmental processes. Built to look good for a range of activities and outdoor settings, the boot has a Gore-Tex® bootie construction to...
      $41.50
      $125.50
      $41.50
      Unit price
      / per 
      • Brown
    • Sale
      GreenStride™ TBL® Originals Ultra Waterproof Boot for Men in Light Brown Timberland OutletGreenStride™ TBL® Originals Ultra Waterproof Boot for Men in Light Brown Timberland Outlet

      GreenStride™ TBL® Originals Ultra Waterproof Boot for Men in Light Brown Timberland Outlet

      Ultra adventure. A new look at our men’s classic waterproof boots with natural comfort. New GreenStride™ soles are made using 75% natural sugar cane and rubber from trees. TimberDry™ linings are made of at least 50% recycled plastic diverted from landfills and the upper...
      $47.99
      $159.59
      $47.99
      Unit price
      / per 
      • Light Brown
    • Sale
      Killington Chukka Boot for Men in Light Brown Timberland OnlineKillington Chukka Boot for Men in Light Brown Timberland Online

      Killington Chukka Boot for Men in Light Brown Timberland Online

      Our Killington men's leather chukkas mix the performance and comfort of a trainer with sleek leather uppers sourced from tanneries that are audited for their environmental efforts during the tanning process. Plus, they feature SensorFlex™ technology for comfort, flexibility and stability on any terrain.CARE...
      $36.50
      $110.59
      $36.50
      Unit price
      / per 
      • Light Brown
    • Sale
      Timberland® Heritage 6 Inch Winter Boot for Men in Black/Camo Timberland SaleTimberland® Heritage 6 Inch Winter Boot for Men in Black/Camo Timberland Sale

      Timberland® Heritage 6 Inch Winter Boot for Men in Black/Camo Timberland Sale

      This men's Timberland® Heritage 6-inch boot is constructed with a premium upper using Better Leather sourced from a sustainable tannery rated silver for its environmental processes. Another eco-conscious material is the durable ReBOTL™ fabric lining, which contains at least 50% recycled plastic. Helping to...
      $49.00
      $164.00
      $49.00
      Unit price
      / per 
      • Black
    • Sale
      GreenStride™ Edge Boot for Men in Yellow Timberland DiscountGreenStride™ Edge Boot for Men in Yellow Timberland Discount

      GreenStride™ Edge Boot for Men in Yellow Timberland Discount

      Adventure on the edge. GreenStride™ soles are one of the most eco-conscious and comfortable experiences we’ve ever invented. And now we bring them to boots. We use a 75% combination of renewable natural sugar cane and rubber from trees to make them naturally comfortable,...
      $45.50
      $151.50
      $45.50
      Unit price
      / per 
      • Yellow
    • Sale
      GreenStride™ Edge Boot for Men in Black Timberland USGreenStride™ Edge Boot for Men in Black Timberland US

      GreenStride™ Edge Boot for Men in Black Timberland US

      Adventure on the edge. GreenStride™ soles are one of the most eco-conscious and comfortable experiences we’ve ever invented. And now we bring them to boots. We use a 75% combination of renewable natural sugar cane and rubber from trees to make them naturally comfortable,...
      $45.50
      $150.99
      $45.50
      Unit price
      / per 
      • Black
    • Sale
      Treeline Chukka for Men in Dark Green Timberland On SaleTreeline Chukka for Men in Dark Green Timberland On Sale

      Treeline Chukka for Men in Dark Green Timberland On Sale

      This men's chukka is made with premium Better Leather sourced from a sustainable tannery rated silver for its environmental process. The lining inside is also crafted with durable ReBOTL™ fabric containing at least 50% recycled plastic. Putting extra comfort between you and the ground,...
      $39.50
      $119.59
      $39.50
      Unit price
      / per 
      • Dark Green
    • Sale
      Treeline Chukka for Men in Beige Timberland For SaleTreeline Chukka for Men in Beige Timberland For Sale

      Treeline Chukka for Men in Beige Timberland For Sale

      This men's chukka is made with premium Better Leather sourced from a sustainable tannery rated silver for its environmental process. The lining inside is also crafted with durable ReBOTL™ fabric containing at least 50% recycled plastic. Putting extra comfort between you and the ground,...
      $39.59
      $120.00
      $39.59
      Unit price
      / per 
      • Beige
    Showing 61 -90 of 408 total
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