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  • 35 items in Men Leather Boots

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    • 2 colors
      Extended Widths
      Steve Madden Harken Chukka Boots
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      $90.00
      Sale $69.99
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      (177)
    • 2 colors
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      Timberland Men's 6" Premium Waterproof Boot
      Everyday Value
      $189.98
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      (508)
    • 2 colors
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      Timberland Men's 6" Boot, Created for Macy's
      LAST ACT select colors
      $190.00
      Now $94.93 - 190.00
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      (153)
    • Timberland Men's 6" Premium Fabric Boots
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      $150.00
      Now $74.93
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      (1)
    • Extended Widths
      Timberland Men's 6" Basic Waterproof Boot
      Limited-Time Special
      $145.00
      Sale $109.99
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      (345)
    • 3 colors
      Johnston & Murphy Copeland Chukka Boots
      $159.00
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      (30)
    • Timberland Men's Kendrick Chukka Lace-Up Boots
      $140.00
      Now $91.00
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      (17)
    • Extended Widths
      Timberland Men's Earthkeeper Original 6" Boot
      Everyday Value
      $149.98
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      (387)
    • Extended Widths
      Rockport Men's Classic Break Chukka Boot
      Limited-Time Special
      $135.00
      Sale $80.99
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      (32)
    • HUGO Men's Dress Appeal Zip Boots
      $295.00
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      (1)
    • UGG® Men's Hannen TL Boots
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      $230.00
      Now $114.93
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      (234)
    • 2 colors
      Extended Widths
      Florsheim Men's Duke Bike Toe Ankle Boot
      $135.00
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      (290)
    • 3 colors
      Extended Widths
      Stacy Adams Men's Madison Boot
      $135.00
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      (164)
    • 5 colors
      Extended Widths
      Eastland Men's Lumber Up Boot
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      $125.00 - 130.00
      Sale $111.99 - 116.99
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      (14)
    • Extended Widths
      Rockport Men's Rugged Bucs H20 Waterproof Plain Toe Boots
      $120.00
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      (84)
    • Timberland Men's Kendrick Chelsea Boots
      $140.00
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      (14)
    • 2 colors
      Extended Widths
      Florsheim Men's Essex Moc Toe Ankle Boot
      $130.00
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      (137)
    • 3 colors
      Clarks Men's Original Desert Boots
      $130.00
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      (202)
    • ALDO Men's Sthephanus Double-Zip Boots
      $160.00
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    • Eastland Men's Chester Boots
      Limited-Time Special
      $130.00
      Sale $116.99
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    • Calvin Klein Men's Albe Nappa Leather Chukka Boots
      Limited-Time Special
      $150.00
      Sale $89.99
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    • 9 colors
      Extended Widths
      Eastland Men's Seneca Boot
      Limited-Time Special
      $110.00
      Sale $81.99
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      (6)
    • Timberland Men's New Market Scuff Proof II 6'' Waterproof Boots
      $190.00
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      (65)
    • 2 colors
      Eastland High Fidelity Lace-Up Boots
      Limited-Time Special
      $125.00
      Sale $111.99
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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)
    • 2 colors
      Carlos by Carlos Santana Men's Corazon Chukka Boots
      $159.00
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    • 2 colors
      Eastland Daily Double Side-Gore Boots
      Limited-Time Special
      $110.00 - 115.00
      Sale $98.99 - 102.99
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      (3)
    • 2 colors
      UGG® Men's Freamon Leather Chukka Boots
      $150.00
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      (22)
    • UGG® Men's Neumel Chukka Boots
      $140.00
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      (15)
    • UGG® Men's Yucca Waterproof Boots
      $120.00
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      (48)
    • Extended Widths
      Rockport Men's Essential Details Waterproof Chukka Boot
      $120.00
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      (48)
    • 2 colors
      Eastland Men's Sherman 1955 Boots
      $225.00
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      (2)