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Mens

  1. Men’s Britton Road Mid Lace-Up Waterproof Chukka Boot Men’s Britton Road Mid Lace-Up Waterproof Chukka Boot
    Men’s Britton Road Mid Lace-Up Waterproof Chukka Boot
    $269.99
  2. Men’s Britton Road Mid Lace-Up Waterproof Chukka Boot Men’s Britton Road Mid Lace-Up Waterproof Chukka Boot
    Men’s Britton Road Mid Lace-Up Waterproof Chukka Boot
    $269.99
  3. Men's Atwells Ave Waterproof Boot Men's Atwells Ave Waterproof Boot
    Men's Atwells Ave Waterproof Boot
    $269.99
  4. Men’s Newmarket Mid Lace-Up Chukka Boot Men’s Newmarket Mid Lace-Up Chukka Boot
    Men’s Newmarket Mid Lace-Up Chukka Boot
    $269.99
  5. Men’s Newmarket Mid Lace-Up Chukka Boot Men’s Newmarket Mid Lace-Up Chukka Boot
    Men’s Newmarket Mid Lace-Up Chukka Boot
    $269.99
  6. Men's GreenStride™ Atwells Ave Waterproof Chukka Boot Men's GreenStride™ Atwells Ave Waterproof Chukka Boot
    Men's GreenStride™ Atwells Ave Waterproof Chukka Boot
    $279.99
  7. Men's Icon Waterproof Chukka Boot Men's Icon Waterproof Chukka Boot
    Men's Icon Waterproof Chukka Boot
    $299.99
  8. Men's Maple Grove Chukka Men's Maple Grove Chukka
    Men's Maple Grove Chukka
    $199.99 $259.99
  9. Men's Attleboro Mid Lace-Up Chukka Men's Attleboro Mid Lace-Up Chukka
    Men's Attleboro Mid Lace-Up Chukka
    $299.99
  10. Men's Arbor Road Waterproof Chukka Men's Arbor Road Waterproof Chukka
    Men's Arbor Road Waterproof Chukka
    $159.99 $299.99
  11. Men's Redwood Falls Mid Lace-Up Waterproof Chukka Boot Men's Redwood Falls Mid Lace-Up Waterproof Chukka Boot
    Men's Redwood Falls Mid Lace-Up Waterproof Chukka Boot
    $279.99
  12. Men's Redwood Falls Waterproof Chukka Boot Men's Redwood Falls Waterproof Chukka Boot
    Men's Redwood Falls Waterproof Chukka Boot
    $279.99
  13. Men's Ashwood Park Lace Up Chukka Boot Men's Ashwood Park Lace Up Chukka Boot
    Men's Ashwood Park Lace Up Chukka Boot
    $129.99 $169.99
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Have a look through our men’s Timberland’s sale for  footwear, clothing, and accessories at discounted prices. Explore our iconic range of men's boots and boat shoes, all at great prices. Style a complete Timberland look with our men's clothing sale, featuring t-shirts, jackets, joggers, and more. Don't forget to check out our collection of men's accessories to complete your look from head to toe. Be sure to browse our women's sale and kids sale for deals on everything from the playground to the gym. Sign up for updates to get early access to your favourite boots and men’s clothing on sale. Check out our Black Friday guide for all you need to know about shopping in store or online with Timberland during one of the busiest weekends of the year.