Track Order

Track My Order

Enter your order number to see the status of your order.
This can be found in the My Orders section within your Account

Login
NEED HELP
My List
Stores
Wear now and pay later with Afterpay
Menu
Items In Cart
Search

Footwear

Shop By
Now Shopping by
  1. Material Leather Remove This Item
Clear All
Shopping Options
Category
  1. Boots
  2. Sneakers
  3. Shoes
  4. Dress Shoes
  5. Hiking Boots & Shoes
  6. Boat Shoes & Sandals
  7. Chukka
Gender
  1. Men
  2. Women
Size
3/4
Size US Mens
6
7
8
9
10
11
12
13
14
15
Size US Womens
9
10
11
Size EU
39
40
41.5
42
43
44
45
46
47.5
49
50
Size UK
5.5
6.5
7
7.5
8
8.5
9
9.5
10.5
11.5
12.5
13.5
14.5
View as Grid List

Items 61-120 of 122

Arrow filters
  1. Men's Attleboro Mid Lace-Up Chukka Men's Attleboro Mid Lace-Up Chukka
    Men's Attleboro Mid Lace-Up Chukka
    $299.99
    Add to List View
  2. Men's Winsor Park Chukka Men's Winsor Park Chukka
    Men's Winsor Park Chukka
    $179.99 $259.99
    Add to List View
  3. Men's Winsor Park Chukka Men's Winsor Park Chukka
    Men's Winsor Park Chukka
    $179.99 $259.99
    Add to List View
  4. Men's 6-Inch Alburn Boot Men's 6-Inch Alburn Boot
    Men's 6-Inch Alburn Boot
    $249.99 $279.99
    Add to List View
  5. Men's 6-Inch Alburn Boot Men's 6-Inch Alburn Boot
    Men's 6-Inch Alburn Boot
    $249.99 $279.99
    Add to List View
  6. Men's Waterproof Field Boot Men's Waterproof Field Boot
    Men's Waterproof Field Boot
    $179.99 $259.99
    Add to List View
  7. Men's Pro Hypercharge 6-Inch Composite Toe Waterproof Work Boot Men's Pro Hypercharge 6-Inch Composite Toe Waterproof Work Boot
    Men's Pro Hypercharge 6-Inch Composite Toe Waterproof Work Boot
    $179.99 $299.99
    Add to List View
  8. Men's Pro Hypercharge 6-Inch Composite Toe Waterproof Work Boot Men's Pro Hypercharge 6-Inch Composite Toe Waterproof Work Boot
    Men's Pro Hypercharge 6-Inch Composite Toe Waterproof Work Boot
    $179.99 $299.99
    Add to List View
  9. Men's Pro Reaxion Composite Toe Mid Sneaker Men's Pro Reaxion Composite Toe Mid Sneaker
    Men's Pro Reaxion Composite Toe Mid Sneaker
    $149.99
    Add to List View
  10. Men's 6-Inch Premium Waterproof Boot Men's 6-Inch Premium Waterproof Boot
    Men's 6-Inch Premium Waterproof Boot
    $229.99 $329.99
    Add to List View
  11. Men's Atwells Ave Waterproof Boot Men's Atwells Ave Waterproof Boot
    Men's Atwells Ave Waterproof Boot
    $184.99 $269.99
    Add to List View
  12. Men's Original 6-Inch Boot Men's Original 6-Inch Boot
    Men's Original 6-Inch Boot
    $189.99 $319.99
    Add to List View
  13. Men's Original 6-Inch Boot Men's Original 6-Inch Boot
    Men's Original 6-Inch Boot
    $209.99 $319.99
    Add to List View
  14. 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
    Add to List View
  15. 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
    Add to List View
  16. Men's Premium 6-Inch Waterproof Boot Men's Premium 6-Inch Waterproof Boot
    Men's Premium 6-Inch Waterproof Boot
    $189.99 $349.99
    Add to List View
  17. 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
    Add to List View
  18. Men's Pro Ballast 6-Inch Steel Toe Work Boot Men's Pro Ballast 6-Inch Steel Toe Work Boot
    Men's Pro Ballast 6-Inch Steel Toe Work Boot
    $119.99 $259.99
    Add to List View
  19. Men's 3-Eye Lug Handsewn Boat Shoe Men's 3-Eye Lug Handsewn Boat Shoe
    Men's 3-Eye Lug Handsewn Boat Shoe
    $174.99 $249.99
    Add to List View
  20. Men's 3-Eye Lug Handsewn Boat Shoe Men's 3-Eye Lug Handsewn Boat Shoe
    Men's 3-Eye Lug Handsewn Boat Shoe
    $174.99 $249.99
    Add to List View
  21. 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
    Add to List View
  22. 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
    Add to List View
  23. Men's Atwells Ave Waterproof Boot Men's Atwells Ave Waterproof Boot
    Men's Atwells Ave Waterproof Boot
    $269.99
    Add to List View
  24. Men's Newmarket II Boot Men's Newmarket II Boot
    Men's Newmarket II Boot
    $229.99 $329.99
    Add to List View
  25. Men's Westmore Chukka Men's Westmore Chukka
    Men's Westmore Chukka
    $179.99 $269.99
    Add to List View
  26. Men's Westmore Chukka Men's Westmore Chukka
    Men's Westmore Chukka
    $179.99 $269.99
    Add to List View
  27. Men's Waterproof Field Boot Men's Waterproof Field Boot
    Men's Waterproof Field Boot
    $179.99 $259.99
    Add to List View
  28. 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
    Add to List View
  29. Men's Westmore Chukka Men's Westmore Chukka
    Men's Westmore Chukka
    $179.99 $269.99
    Add to List View
  30. Men’s Timberland® C.F. Stead™ Indigo Suede Heritage 6-Inch Boot Men’s Timberland® C.F. Stead™ Indigo Suede Heritage 6-Inch Boot
    Men’s Timberland® C.F. Stead™ Indigo Suede Heritage 6-Inch Boot
    $299.99 $329.99
    Add to List View
  31. Men's Newmarket II Boot Men's Newmarket II Boot
    Men's Newmarket II Boot
    $229.99 $329.99
    Add to List View
  32. 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
    Add to List View
  33. Men's Classic 6-Inch Waterproof Boot Men's Classic 6-Inch Waterproof Boot
    Men's Classic 6-Inch Waterproof Boot
    $189.99 $279.99
    Add to List View
  34. 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
    Add to List View
  35. Men's Redwood Falls Waterproof Boot Men's Redwood Falls Waterproof Boot
    Men's Redwood Falls Waterproof Boot
    $299.99
    Add to List View
  36. Men's Premium 6-Inch Waterproof Boot Men's Premium 6-Inch Waterproof Boot
    Men's Premium 6-Inch Waterproof Boot
    $179.99 $349.99
    Add to List View
  37. Men's Atwells Ave Waterproof Boots Men's Atwells Ave Waterproof Boots
    Men's Atwells Ave Waterproof Boots
    $179.99 $269.99
    Add to List View
  38. Men's Premium Chukka Men's Premium Chukka
    Men's Premium Chukka
    $209.99 $329.99
    Add to List View
  39. Men's 3-Eye Lug Handsewn Boat Shoe Men's 3-Eye Lug Handsewn Boat Shoe
    Men's 3-Eye Lug Handsewn Boat Shoe
    $174.99 $249.99
    Add to List View
  40. Men's Westmore Moc-Toe Chukka Men's Westmore Moc-Toe Chukka
    Men's Westmore Moc-Toe Chukka
    $139.99 $269.99
    Add to List View
  41. Men's Killington Trekker Low Men's Killington Trekker Low
    Men's Killington Trekker Low
    $89.99 $219.99
    Add to List View
  42. Men's 3-Eye Lug Handsewn Boat Shoe Men's 3-Eye Lug Handsewn Boat Shoe
    Men's 3-Eye Lug Handsewn Boat Shoe
    $174.99 $249.99
    Add to List View
  43. Men's Classic Waterproof Chukka Men's Classic Waterproof Chukka
    Men's Classic Waterproof Chukka
    $94.99 $279.99
    Add to List View
  44. Men's Davis Square Oxford Basic Sneaker Men's Davis Square Oxford Basic Sneaker
    Men's Davis Square Oxford Basic Sneaker
    $59.99 $179.99
    Add to List View
  45. Men's Classic 6-Inch Waterproof Boot Men's Classic 6-Inch Waterproof Boot
    Men's Classic 6-Inch Waterproof Boot
    $159.99 $279.99
    Add to List View
  46. Men's GreenStride™ Atwells Ave Waterproof Chukka Boot Men's GreenStride™ Atwells Ave Waterproof Chukka Boot
    Men's GreenStride™ Atwells Ave Waterproof Chukka Boot
    $179.99 $259.99
    Add to List View
  47. 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
    Add to List View
  48. Men's Atwell Ave Chelsea Boot Men's Atwell Ave Chelsea Boot
    Men's Atwell Ave Chelsea Boot
    $149.99 $259.99
    Add to List View
  49. Men's Classic Boat Shoe Men's Classic Boat Shoe
    Men's Classic Boat Shoe
    $119.99 $199.99
    Add to List View
  50. 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
    Add to List View
  51. 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
    Add to List View
  52. Men's Newmarket II Moc Toe Chukka
    Men's Newmarket II Moc Toe Chukka
    $99.99 $249.99
    Add to List View
  53. 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
    Add to List View
  54. Men's Redwood Falls Waterproof Boot Men's Redwood Falls Waterproof Boot
    Men's Redwood Falls Waterproof Boot
    $279.99
    Add to List View
  55. Men's 6-Inch Alburn Boot Men's 6-Inch Alburn Boot
    Men's 6-Inch Alburn Boot
    $119.99 $269.99
    Add to List View
  56. Men's Bradstreet Plain-Toe Oxford Shoe Men's Bradstreet Plain-Toe Oxford Shoe
    Men's Bradstreet Plain-Toe Oxford Shoe
    $79.99 $219.99
    Add to List View
  57. Men's Cedar Bay Boat Shoe Men's Cedar Bay Boat Shoe
    Men's Cedar Bay Boat Shoe
    $229.99
    Add to List View
  58. Women’s Garrison Trail WP Low Hiker Boots Women’s Garrison Trail WP Low Hiker Boots
    Women’s Garrison Trail WP Low Hiker Boots
    $129.99 $229.99
    Add to List View
  59. Men’s Garrison Trail Hiking Sneakers Men’s Garrison Trail Hiking Sneakers
    Men’s Garrison Trail Hiking Sneakers
    $109.99 $199.99
    Add to List View
  60. Men’s Garrison Trail WP Mid Hiker Boots Men’s Garrison Trail WP Mid Hiker Boots
    Men’s Garrison Trail WP Mid Hiker Boots
    $129.99 $259.99
    Add to List View
Page
per page
Explore your favourite Men's Timberland Footwear at discounted prices in our men's sale. Find the popular styles like our Men's Premium 6-Inch Boots or our range of Men's Hiking Boots. For something more versatile that will take you from casual to formal, browse our collection of Men's Boat Shoes. For a full Timberland look from head to toe, make sure to browse our range of Men's Accessories. If you're planning to shop our Black Friday sale, sign up to our mailing list 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 Footwear Sale online today.