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Items 61-99 of 99

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  1. Men's Arbor Road Waterproof Chukka Men's Arbor Road Waterproof Chukka
    Men's Arbor Road Waterproof Chukka
    $199.99 $299.99
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  2. Men's Winsor Park Chukka Men's Winsor Park Chukka
    Men's Winsor Park Chukka
    $179.99 $259.99
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  3. Men's Winsor Park Chukka Men's Winsor Park Chukka
    Men's Winsor Park Chukka
    $179.99 $259.99
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  4. Men's Mt. Maddsen Mid Lace-Up Hiking Boot Men's Mt. Maddsen Mid Lace-Up Hiking Boot
    Men's Mt. Maddsen Mid Lace-Up Hiking Boot
    $179.99 $259.99
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  5. Men's Mt. Maddsen Mid Lace-Up Hiking Boot Men's Mt. Maddsen Mid Lace-Up Hiking Boot
    Men's Mt. Maddsen Mid Lace-Up Hiking Boot
    $179.99 $259.99
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  6. Men's 50th Anniversary Edition 6-Inch Boot Men's 50th Anniversary Edition 6-Inch Boot
    Men's 50th Anniversary Edition 6-Inch Boot
    $159.99 $349.99
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  7. Men's 50th Anniversary Edition 6-Inch Boot Men's 50th Anniversary Edition 6-Inch Boot
    Men's 50th Anniversary Edition 6-Inch Boot
    $159.99 $349.99
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  8. Men's 50th Anniversary Edition 6-Inch Boot Men's 50th Anniversary Edition 6-Inch Boot
    Men's 50th Anniversary Edition 6-Inch Boot
    $139.99 $349.99
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  9. Men's 50th Anniversary Edition 6-Inch Boot Men's 50th Anniversary Edition 6-Inch Boot
    Men's 50th Anniversary Edition 6-Inch Boot
    $139.99 $349.99
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  10. Men's Original 6-Inch Boot Men's Original 6-Inch Boot
    Men's Original 6-Inch Boot
    $209.99 $319.99
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  11. Men's Heritage 6-Inch Waterproof Boots Men's Heritage 6-Inch Waterproof Boots
    Men's Heritage 6-Inch Waterproof Boots
    $199.99 $329.99
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  12. Men's Premium 6-Inch Waterproof Boot Men's Premium 6-Inch Waterproof Boot
    Men's Premium 6-Inch Waterproof Boot
    $229.99 $349.99
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  13. Men's Original 6-Inch Boot Men's Original 6-Inch Boot
    Men's Original 6-Inch Boot
    $129.99 $319.99
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  14. Men's Atwells Ave Waterproof Boot Men's Atwells Ave Waterproof Boot
    Men's Atwells Ave Waterproof Boot
    $129.99 $269.99
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  15. Men's Premium 6-Inch Waterproof Boot Men's Premium 6-Inch Waterproof Boot
    Men's Premium 6-Inch Waterproof Boot
    $199.99 $349.99
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  16. Men's Westmore Moc-Toe Chukka Men's Westmore Moc-Toe Chukka
    Men's Westmore Moc-Toe Chukka
    $99.99 $269.99
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  17. Men's 3-Eye Lug Handsewn Boat Shoe Men's 3-Eye Lug Handsewn Boat Shoe
    Men's 3-Eye Lug Handsewn Boat Shoe
    $139.99 $249.99
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  18. Men's 3-Eye Lug Handsewn Boat Shoe Men's 3-Eye Lug Handsewn Boat Shoe
    Men's 3-Eye Lug Handsewn Boat Shoe
    $139.99 $249.99
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  19. PREMIUM 6 INCH LACE UP BOOT
    PREMIUM 6 INCH LACE UP BOOT
    $239.99 $349.99
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  20. Men's Premium 6-Inch Waterproof Boot Men's Premium 6-Inch Waterproof Boot
    Men's Premium 6-Inch Waterproof Boot
    $229.99 $349.99
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  21. BALLAST 6 IN STEEL TOE WORK BOOT
    BALLAST 6 IN STEEL TOE WORK BOOT
    $119.99 $259.99
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  22. Men's 3-Eye Lug Handsewn Boat Shoe Men's 3-Eye Lug Handsewn Boat Shoe
    Men's 3-Eye Lug Handsewn Boat Shoe
    $119.99 $229.99
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  23. Men's 3-Eye Lug Handsewn Boat Shoe Men's 3-Eye Lug Handsewn Boat Shoe
    Men's 3-Eye Lug Handsewn Boat Shoe
    $119.99 $229.99
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  24. Men's 3-Eye Lug Handsewn Boat Shoe Men's 3-Eye Lug Handsewn Boat Shoe
    Men's 3-Eye Lug Handsewn Boat Shoe
    $129.99 $249.99
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  25. Men's Westmore Chukka Men's Westmore Chukka
    Men's Westmore Chukka
    $179.99 $269.99
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  26. Men's Timberland® C.F. Stead™ Indigo Suede Euro Hiker Boot Men's Timberland® C.F. Stead™ Indigo Suede Euro Hiker Boot
    Men's Timberland® C.F. Stead™ Indigo Suede Euro Hiker Boot
    $179.99 $269.99
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  27. Men's Classic Boat Shoe Men's Classic Boat Shoe
    Men's Classic Boat Shoe
    $119.99 $199.99
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  28. Redwood Falls Waterproof Redwood Falls Waterproof
    Redwood Falls Waterproof
    $199.99 $299.99
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  29. Men's Timberland® C.F. Stead™ Indigo Suede 3-Eye Lug Handsewn Boat Shoe Men's Timberland® C.F. Stead™ Indigo Suede 3-Eye Lug Handsewn Boat Shoe
    Men's Timberland® C.F. Stead™ Indigo Suede 3-Eye Lug Handsewn Boat Shoe
    $169.99 $249.99
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  30. Men's Maple Grove Chukka Men's Maple Grove Chukka
    Men's Maple Grove Chukka
    $179.99 $259.99
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  31. Men's Atwells Ave Waterproof Boots Men's Atwells Ave Waterproof Boots
    Men's Atwells Ave Waterproof Boots
    $129.99 $269.99
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  32. Men's Newmarket II Boot Men's Newmarket II Boot
    Men's Newmarket II Boot
    $159.99 $329.99
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  33. Men's Premium 6-Inch Waterproof Boot Men's Premium 6-Inch Waterproof Boot
    Men's Premium 6-Inch Waterproof Boot
    $129.99 $349.99
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  34. NEWMARKET II BOAT CHK
    NEWMARKET II BOAT CHK
    $85.99 $249.99
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  35. Men's Atwell Ave Chelsea Boot Men's Atwell Ave Chelsea Boot
    Men's Atwell Ave Chelsea Boot
    $99.99 $259.99
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  36. Men’s Ski School Timberland® Premium 6 Inch WP Boot Men’s Ski School Timberland® Premium 6 Inch WP Boot
    Men’s Ski School Timberland® Premium 6 Inch WP Boot
    $249.99 $369.99
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  37. Men's Newmarket II Boot Men's Newmarket II Boot
    Men's Newmarket II Boot
    $159.99 $329.99
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  38. Men's GreenStride™ Atwells Ave Waterproof Chukka Boot Men's GreenStride™ Atwells Ave Waterproof Chukka Boot
    Men's GreenStride™ Atwells Ave Waterproof Chukka Boot
    $129.99 $259.99
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  39. EZ LOUNGE SLIP-ON
    EZ LOUNGE SLIP-ON
    $39.99 $179.99
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Find your favourite Men's Timberland apparel, footwear and accessories at a discounted price in our men's sale collection. Explore our popular range of footwear like our Men's Premium 6-Inch Boots or our Men's Boat Shoes at a discounted price. Style a complete Timberland look by browsing our Men's Sale Clothing for Tees, Jackets, Joggers and more. Don't forget to check out our collection of Men's Accessories to complete your look from head to toe. Shopping for someone else? Browse our Women's Sale range and Kid's Sale collection. Planning to shop our Black Friday sale? Find your favourite boots and clothing on sale before anyone by signing up for updates! Browse our Guide to Black Friday for everything you need to know about shopping in store or online with Timberland during one of the busiest weekends of the year. With free shipping and Afterpay options available, shop Timberland Men's Sale online today.