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  • 10 items in Timberland Most Comfortable Shoes

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    • 2 colors
      Extended Widths
      Timberland Men's 6" Premium Waterproof Boot
      Everyday Value
      $189.98
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      (508)
    • Extended Widths
      Timberland Men's 6" Boot, Created for Macy's
      $190.00
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    • 3 colors
      Timberland Men's Piper Cove Leather Boat Shoes
      Limited-Time Special
      $100.00
      Sale $79.99
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      (80)
    • Extended Widths
      Timberland Men's 6" Basic Waterproof Boot
      Limited-Time Special
      $145.00
      Sale $109.99
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      (345)
    • 2 colors
      Timberland Men's Stormbuck Plain Toe Waterproof Derby
      $130.00
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    • Extended Widths
      Timberland Men's Earthkeeper Original 6" Boot
      Everyday Value
      $149.98
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      (387)
    • Timberland Men's Naples Trail Oxfords
      Limited-Time Special
      $120.00
      Sale $99.99
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      (19)
    • Timberland Men's Kendrick Chelsea Boots
      $140.00
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      (14)
    • Timberland Men's Naples Trail Suede Oxfords
      Limited-Time Special
      $120.00
      Sale $99.99
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      (21)
    • Extended Widths
      Timberland Men's 6" Boot, Created for Macy's
      LAST ACT
      $190.00
      Now $94.93
      coupon excluded
      Last Act: Extra savings do not apply
      coupon excluded
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