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  • 37 items in Leather Boots

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    • 4 colors
      Timberland Men's Groveton Hi-Top Sneakers
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      $90.00
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      (198)
    • 2 colors
      Extended Widths
      Steve Madden Harken Chukka Boots
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      $90.00
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      (177)
    • 2 colors
      Extended Widths
      Timberland Men's 6" Premium Waterproof Boot
      Everyday Value
      $189.98
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      (558)
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      Timberland Men's 6" Basic Waterproof Boot
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      $145.00
      Sale $119.99
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      (345)
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      Timberland Men's Earthkeeper Original 6" Boot
      Everyday Value
      $149.98
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      (393)
    • Extended Widths
      Rockport Men's Classic Break Chukka Boot
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      $135.00
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      (32)
    • 3 colors
      Johnston & Murphy Copeland Chukka Boots
      $159.00
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      (30)
    • HUGO Men's Dress Appeal Zip Boots
      $295.00
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      (2)
    • ALDO Men's Sthephanus Double-Zip Boots
      $160.00
      Sale $79.99
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    • Extended Widths
      Rockport Men's Rugged Bucs H20 Waterproof Plain Toe Boots
      $120.00
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      (85)
    • 2 colors
      Extended Widths
      Florsheim Men's Duke Bike Toe Ankle Boot
      $135.00
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      (299)
    • 3 colors
      Extended Widths
      Stacy Adams Men's Madison Boot
      $135.00
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      (164)
    • UGG® Men's Freamon Leather Chukka Boots
      $150.00
      Now $97.50
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    • 3 colors
      Clarks Men's Original Desert Boots
      $130.00
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      (202)
    • Timberland Men's Kendrick Chelsea Boots
      $140.00
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      (15)
    • 5 colors
      Extended Widths
      Eastland Men's Lumber Up Boot
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      $125.00 - 130.00
      Sale $109.99
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      (14)
    • 2 colors
      Eastland Daily Double Side-Gore Boots
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      $110.00 - 115.00
      Sale $98.99
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      (3)
    • 2 colors
      Extended Widths
      Florsheim Men's Essex Moc Toe Ankle Boot
      $130.00
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      (139)
    • Calvin Klein Men's Albe Nappa Leather Chukka Boots
      Limited-Time Special
      $150.00
      Sale $89.99
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    • 2 colors
      Eastland High Fidelity Lace-Up Boots
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      $125.00
      Sale $109.99
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      (1)
    • Stacy Adams Men's Delaney Chukka Boots
      Limited-Time Special
      $105.00
      Sale $62.99
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      (14)
    • Extended Widths
      Timberland Men's 6" Boot, Created for Macy's
      $190.00
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      (153)
    • Eastland Men's Chester Boots
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      $130.00
      Sale $109.99
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    • 9 colors
      Extended Widths
      Eastland Men's Seneca Boot
      Limited-Time Special
      $110.00
      Sale $87.99
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      (6)
    • UGG® Men's Freamon Leather Chukka Boots
      $150.00
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      (22)
    • NEW! Alfani Men's Briar Harness Boots, Created for Macy's
      $99.99
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    • NEW! Alfani Men's Jason Fleece-Lined Leather Boots, Created for Macy's
      $99.99
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    • UGG® Men's Neumel Chukka Boots
      $140.00
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      (15)
    • UGG® Men's Hannen TL Boots
      LAST ACT
      $230.00
      Now $114.93
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      (234)
    • UGG® Men's Yucca Waterproof Boots
      $120.00
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      (48)
    • 2 colors
      Carlos by Carlos Santana Men's Corazon Chukka Boots
      $159.00
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    • 2 colors
      Eastland Men's Sherman 1955 Boots
      $225.00
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      (2)
    • Timberland Men's New Market Scuff Proof II 6'' Waterproof Boots
      $190.00
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      (65)
    • NEW! Bar III Men's Watson Two-Tone Chelsea Boots, Created for Macy's
      $109.99
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    • Nautica Madryn Moc-Toe Boots
      $65.00
      Now $42.25
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      (35)
    • Timberland Men's Kendrick Chukka Lace-Up Boots
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      $140.00
      Now $69.93
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      (19)
    • Timberland Men's 6" Premium Fabric Boots
      LAST ACT
      $150.00
      Now $74.93
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      (379)
    • Showing All 37 Items