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    Timberland Winsor Trail Mid Leather - Mens 8.5 Tan Boot Medium

    Timberland Winsor Trail Mid Leather - Mens 8.5 Tan Boot Medium

    *Trail shoe from Timberland *Better Leather upper *Lace-up front closure *ReBOTL fabric lining *OrthoLite comfort footbed *Rubber rand *GreenStride rubber sole more

    $129.95 $115.97

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    Timberland Eurohiker Leather - Mens 8.5 Green Boot Medium

    Timberland Eurohiker Leather - Mens 8.5 Green Boot Medium

    *This tried-and-true boot is an essential piece of gear for every adventurer *Premium leather upper *5" upper height *100% recycled PET laces *Cushioning EVA midsole *Steel shank for arch support *42% recycled Green Rubber™ sole for durable traction more

    $139.95 $124.97

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    Best Seller
    Timberland Winsor Trail Mid Leather - Mens 11.5 Grey Boot Medium

    Timberland Winsor Trail Mid Leather - Mens 11.5 Grey Boot Medium

    *Trail shoe from Timberland *Better Leather upper *Lace-up front closure *ReBOTL fabric lining *OrthoLite comfort footbed *Rubber rand *GreenStride rubber sole more

    $129.95 $115.97

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    Timberland Eurohiker Leather - Mens 9 Burgundy Boot Medium

    Timberland Eurohiker Leather - Mens 9 Burgundy Boot Medium

    *This tried-and-true boot is an essential piece of gear for every adventurer *Premium leather upper *5" upper height *100% recycled PET laces *Cushioning EVA midsole *Steel shank for arch support *42% recycled Green Rubber™ sole for durable traction more

    $139.95 $124.97

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    Timberland Eurohiker Leather - Mens 9.5 Burgundy Boot Medium

    Timberland Eurohiker Leather - Mens 9.5 Burgundy Boot Medium

    *This tried-and-true boot is an essential piece of gear for every adventurer *Premium leather upper *5" upper height *100% recycled PET laces *Cushioning EVA midsole *Steel shank for arch support *42% recycled Green Rubber™ sole for durable traction more

    $139.95 $124.97

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    Timberland Winsor Trail Mid Leather - Mens 9 Black Boot Medium

    Timberland Winsor Trail Mid Leather - Mens 9 Black Boot Medium

    *Trail shoe from Timberland *Better Leather upper *Lace-up front closure *ReBOTL fabric lining *OrthoLite comfort footbed *Rubber rand *GreenStride rubber sole more

    $129.95 $115.97

    FREE shipping

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    Timberland Winsor Trail Mid Leather - Mens 12 Grey Boot Medium

    Timberland Winsor Trail Mid Leather - Mens 12 Grey Boot Medium

    *Trail shoe from Timberland *Better Leather upper *Lace-up front closure *ReBOTL fabric lining *OrthoLite comfort footbed *Rubber rand *GreenStride rubber sole more

    $129.95 $115.97

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    Timberland Eurohiker Leather - Mens 7.5 Burgundy Boot Medium

    Timberland Eurohiker Leather - Mens 7.5 Burgundy Boot Medium

    *This tried-and-true boot is an essential piece of gear for every adventurer *Premium leather upper *5" upper height *100% recycled PET laces *Cushioning EVA midsole *Steel shank for arch support *42% recycled Green Rubber™ sole for durable traction more

    $139.95 $124.97

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    Timberland Winsor Trail Mid Leather - Mens 9 Tan Boot Medium

    Timberland Winsor Trail Mid Leather - Mens 9 Tan Boot Medium

    *Trail shoe from Timberland *Better Leather upper *Lace-up front closure *ReBOTL fabric lining *OrthoLite comfort footbed *Rubber rand *GreenStride rubber sole more

    $129.95 $115.97

    FREE shipping

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    Timberland Eurohiker Leather - Mens 12 Green Boot Medium

    Timberland Eurohiker Leather - Mens 12 Green Boot Medium

    *This tried-and-true boot is an essential piece of gear for every adventurer *Premium leather upper *5" upper height *100% recycled PET laces *Cushioning EVA midsole *Steel shank for arch support *42% recycled Green Rubber™ sole for durable traction more

    $139.95 $124.97

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    Timberland Winsor Trail Mid Leather - Mens 10.5 Grey Boot Medium

    Timberland Winsor Trail Mid Leather - Mens 10.5 Grey Boot Medium

    *Trail shoe from Timberland *Better Leather upper *Lace-up front closure *ReBOTL fabric lining *OrthoLite comfort footbed *Rubber rand *GreenStride rubber sole more

    $129.95 $115.97

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    Timberland Eurohiker Leather - Mens 7.5 Brown Boot Medium

    Timberland Eurohiker Leather - Mens 7.5 Brown Boot Medium

    *This tried-and-true boot is an essential piece of gear for every adventurer *Premium leather upper *5" upper height *100% recycled PET laces *Cushioning EVA midsole *Steel shank for arch support *42% recycled Green Rubber™ sole for durable traction more

    $139.95 $124.97

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    Timberland Eurohiker Leather - Mens 8.5 Burgundy Boot Medium

    Timberland Eurohiker Leather - Mens 8.5 Burgundy Boot Medium

    *This tried-and-true boot is an essential piece of gear for every adventurer *Premium leather upper *5" upper height *100% recycled PET laces *Cushioning EVA midsole *Steel shank for arch support *42% recycled Green Rubber™ sole for durable traction more

    $139.95 $124.97

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    Timberland Eurohiker Leather - Mens 9 Green Boot Medium

    Timberland Eurohiker Leather - Mens 9 Green Boot Medium

    *This tried-and-true boot is an essential piece of gear for every adventurer *Premium leather upper *5" upper height *100% recycled PET laces *Cushioning EVA midsole *Steel shank for arch support *42% recycled Green Rubber™ sole for durable traction more

    $139.95 $124.97

    FREE shipping

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    Timberland Winsor Trail Mid Leather - Mens 9.5 Grey Boot Medium

    Timberland Winsor Trail Mid Leather - Mens 9.5 Grey Boot Medium

    *Trail shoe from Timberland *Better Leather upper *Lace-up front closure *ReBOTL fabric lining *OrthoLite comfort footbed *Rubber rand *GreenStride rubber sole more

    $129.95 $115.97

    FREE shipping

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    Timberland Winsor Trail Mid Leather - Mens 8.5 Black Boot Medium

    Timberland Winsor Trail Mid Leather - Mens 8.5 Black Boot Medium

    *Trail shoe from Timberland *Better Leather upper *Lace-up front closure *ReBOTL fabric lining *OrthoLite comfort footbed *Rubber rand *GreenStride rubber sole more

    $129.95 $115.97

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    Timberland Eurohiker Leather - Mens 11 Brown Boot Medium

    Timberland Eurohiker Leather - Mens 11 Brown Boot Medium

    *This tried-and-true boot is an essential piece of gear for every adventurer *Premium leather upper *5" upper height *100% recycled PET laces *Cushioning EVA midsole *Steel shank for arch support *42% recycled Green Rubber™ sole for durable traction more

    $139.95 $124.97

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    Timberland Winsor Trail Mid Leather - Mens 8 Grey Boot Medium

    Timberland Winsor Trail Mid Leather - Mens 8 Grey Boot Medium

    *Trail shoe from Timberland *Better Leather upper *Lace-up front closure *ReBOTL fabric lining *OrthoLite comfort footbed *Rubber rand *GreenStride rubber sole more

    $129.95 $115.97

    FREE shipping

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    Timberland Winsor Trail Mid Leather - Mens 10 Black Boot Medium

    Timberland Winsor Trail Mid Leather - Mens 10 Black Boot Medium

    *Trail shoe from Timberland *Better Leather upper *Lace-up front closure *ReBOTL fabric lining *OrthoLite comfort footbed *Rubber rand *GreenStride rubber sole more

    $129.95 $115.97

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    Men's Timberland® Earthkeepers® Original Leather Boot by Timberland in Brown (Size 9 M)

    Men's Timberland® Earthkeepers® Original Leather Boot by Timberland in Brown (Size 9 M)

    Timberland's famous Earthkeepers boot comes to KingSize. Now better than ever, in an eco-conscious design featuring linings and laces made of recycled plastic bottles and an outsole of 15% recycled rubber. Premium full-grain leather upperBreathable... more

    $175.99 $159.99

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    Timberland Maple Grove Fabric/Leather Chukka - Mens 8 Tan Boot Medium

    Timberland Maple Grove Fabric/Leather Chukka - Mens 8 Tan Boot Medium

    *Fabric/leather chukka from Timberland *Upper is made with leather sourced from farms that use regenerative agriculture practices *ReBOTL fabric lining *Lightly cushioned footbed *Rubber midsole *Rubber outsoles from farms committed to regenerative... more

    $129.95 $116.97

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    Men's Timberland® Chocorua Trail Waterproof Hiking Boot by Timberland in Black (Size 9 M)

    Men's Timberland® Chocorua Trail Waterproof Hiking Boot by Timberland in Black (Size 9 M)

    The legendary Chocorua waterproof hiking boots, now built for the big and tall guy. The Chocorua is built to withstand the elements: Gore-Tex membranes keep feet dry and the leather upper is waterproof.Premium full-grain waterproof leather upperPadded... more

    $154.99 $138.99

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    Men's Timberland® Chocorua Trail Waterproof Hiking Boot by Timberland in Black (Size 12 M)

    Men's Timberland® Chocorua Trail Waterproof Hiking Boot by Timberland in Black (Size 12 M)

    The legendary Chocorua waterproof hiking boots, now built for the big and tall guy. The Chocorua is built to withstand the elements: Gore-Tex membranes keep feet dry and the leather upper is waterproof.Premium full-grain waterproof leather upperPadded... more

    $154.99 $138.99

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    Men's Timberland® Chocorua Trail Waterproof Hiking Boot by Timberland in Brown (Size 11 M)

    Men's Timberland® Chocorua Trail Waterproof Hiking Boot by Timberland in Brown (Size 11 M)

    The legendary Chocorua waterproof hiking boots, now built for the big and tall guy. The Chocorua is built to withstand the elements: Gore-Tex membranes keep feet dry and the leather upper is waterproof.Premium full-grain waterproof leather upperPadded... more

    $154.99 $138.99

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    Wide Width Men's Timberland® Chocorua Trail Waterproof Hiking Boot by Timberland in Black (Size 10 W)

    Wide Width Men's Timberland® Chocorua Trail Waterproof Hiking Boot by Timberland in Black (Size 10 W)

    The legendary Chocorua waterproof hiking boots, now built for the big and tall guy. The Chocorua is built to withstand the elements: Gore-Tex membranes keep feet dry and the leather upper is waterproof.Premium full-grain waterproof leather upperPadded... more

    $154.99 $138.99

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    Men's Timberland® Chocorua Trail Waterproof Hiking Boot by Timberland in Brown (Size 10 1/2 M)

    Men's Timberland® Chocorua Trail Waterproof Hiking Boot by Timberland in Brown (Size 10 1/2 M)

    The legendary Chocorua waterproof hiking boots, now built for the big and tall guy. The Chocorua is built to withstand the elements: Gore-Tex membranes keep feet dry and the leather upper is waterproof.Premium full-grain waterproof leather upperPadded... more

    $154.99 $138.99

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    Wide Width Men's Timberland® Chocorua Trail Waterproof Hiking Boot by Timberland in Black (Size 10 1/2 W)

    Wide Width Men's Timberland® Chocorua Trail Waterproof Hiking Boot by Timberland in Black (Size 10 1/2 W)

    The legendary Chocorua waterproof hiking boots, now built for the big and tall guy. The Chocorua is built to withstand the elements: Gore-Tex membranes keep feet dry and the leather upper is waterproof.Premium full-grain waterproof leather upperPadded... more

    $154.99 $138.99

    go to store
    Wide Width Men's Timberland® Chocorua Trail Waterproof Hiking Boot by Timberland in Brown (Size 9 W)

    Wide Width Men's Timberland® Chocorua Trail Waterproof Hiking Boot by Timberland in Brown (Size 9 W)

    The legendary Chocorua waterproof hiking boots, now built for the big and tall guy. The Chocorua is built to withstand the elements: Gore-Tex membranes keep feet dry and the leather upper is waterproof.Premium full-grain waterproof leather upperPadded... more

    $154.99 $138.99

    go to store
    Wide Width Men's Timberland® Chocorua Trail Waterproof Hiking Boot by Timberland in Brown (Size 13 W)

    Wide Width Men's Timberland® Chocorua Trail Waterproof Hiking Boot by Timberland in Brown (Size 13 W)

    The legendary Chocorua waterproof hiking boots, now built for the big and tall guy. The Chocorua is built to withstand the elements: Gore-Tex membranes keep feet dry and the leather upper is waterproof.Premium full-grain waterproof leather upperPadded... more

    $154.99 $138.99

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    Field Waterproof Boot

    Field Waterproof Boot

    Men's Timberland Field Waterproof Boot - Brown - Casual boots Rugged, outdoorsy appeal elevates a well-built boot crafted from waterproof full-grain leather for dry comfort and lasting durability. more

    $185.00

    FREE shipping

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    Men's Timberland® 6-Inch Waterproof Boots by Timberland in Wheat Nubuck (Size 13 M)

    Men's Timberland® 6-Inch Waterproof Boots by Timberland in Wheat Nubuck (Size 13 M)

    These Timberland® 6-Inch Waterproof Boots are designed to hold up to wear and tear, year after year. Ready for the great outdoors, these leather work boots feature seam-sealed waterproof protection and rubber lug outsoles to grip rugged terrain.... more

    $210.99 $169.99

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    Men's Timberland® 6-Inch Waterproof Boots by Timberland in Black (Size 13 M)

    Men's Timberland® 6-Inch Waterproof Boots by Timberland in Black (Size 13 M)

    These Timberland® 6-Inch Waterproof Boots are designed to hold up to wear and tear, year after year. Ready for the great outdoors, these leather work boots feature seam-sealed waterproof protection and rubber lug outsoles to grip rugged terrain.... more

    $210.99 $169.99

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    Attleboro Chukka Boot

    Attleboro Chukka Boot

    Men's Timberland Attleboro Chukka Boot - Black - Casual boots Step out in handsome style with the Attleboro Chukka boot from Timberland. Crafted from premium Timberland leather upper for long-term wear, this boot comes with steel shank for enhanced... more

    $129.99

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    Wide Width Men's Timberland® 6-Inch Waterproof Boots by Timberland in Wheat Nubuck (Size 12 W)

    Wide Width Men's Timberland® 6-Inch Waterproof Boots by Timberland in Wheat Nubuck (Size 12 W)

    These Timberland® 6-Inch Waterproof Boots are designed to hold up to wear and tear, year after year. Ready for the great outdoors, these leather work boots feature seam-sealed waterproof protection and rubber lug outsoles to grip rugged terrain.... more

    $210.99 $169.99

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    Atwells Ave Waterproof Boot

    Atwells Ave Waterproof Boot

    Men's Timberland Atwells Ave Waterproof Boot - Black - Casual boots The Atwells Ave waterproof boot from Timberland is perfect for outdoor adventures. Designed with sustainability in mind, this lace-up boot features a waterproof Better Leather upper... more

    $159.99 $109.98

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    Wide Width Men's Timberland® 6-Inch Waterproof Boots by Timberland in Black (Size 11 W)

    Wide Width Men's Timberland® 6-Inch Waterproof Boots by Timberland in Black (Size 11 W)

    These Timberland® 6-Inch Waterproof Boots are designed to hold up to wear and tear, year after year. Ready for the great outdoors, these leather work boots feature seam-sealed waterproof protection and rubber lug outsoles to grip rugged terrain.... more

    $210.99 $169.99

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    Earthkeepers Original Boot

    Earthkeepers Original Boot

    Men's Timberland Earthkeepers Original Boot - Brown - Casual boots Timberland's flagship Earthkeepers® men's boots are made with recycled/sustainably sourced materials without sacrificing quality or style. This leather lace-up boot is perfect for the... more

    $149.96

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    Wide Width Men's Timberland® Mt.Maddsen Waterproof Hiking Boots by Timberland in Black (Size 11 W)

    Wide Width Men's Timberland® Mt.Maddsen Waterproof Hiking Boots by Timberland in Black (Size 11 W)

    Make footprints on your favorite trail in our Timberland® Mt.Maddsen Waterproof Hiking Boots. Keeping your feet dry in rugged style, these leather hikers take on any terrain and look great with your performance hiking gear and with jeans and a tee.... more

    $145.99 $130.99

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    Wide Width Men's Timberland® 6-Inch Waterproof Boots by Timberland in Black (Size 9 W)

    Wide Width Men's Timberland® 6-Inch Waterproof Boots by Timberland in Black (Size 9 W)

    These Timberland® 6-Inch Waterproof Boots are designed to hold up to wear and tear, year after year. Ready for the great outdoors, these leather work boots feature seam-sealed waterproof protection and rubber lug outsoles to grip rugged terrain.... more

    $210.99 $169.99

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    Wide Width Men's Timberland® 6-Inch Waterproof Boots by Timberland in Black (Size 12 W)

    Wide Width Men's Timberland® 6-Inch Waterproof Boots by Timberland in Black (Size 12 W)

    These Timberland® 6-Inch Waterproof Boots are designed to hold up to wear and tear, year after year. Ready for the great outdoors, these leather work boots feature seam-sealed waterproof protection and rubber lug outsoles to grip rugged terrain.... more

    $210.99 $169.99

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    More information about Men's Shoes

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