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  • 103 items in Men Mens Winter Shoes

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    • 5 colors
      Extended Widths
      Clarks Men's Bushacre 2 Chukka Boots
      Limited-Time Special
      $100.00
      Sale $69.99
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      (22)
    • 2 colors
      Extended Widths
      Steve Madden Harken Chukka Boots
      Limited-Time Special
      $90.00
      Sale $69.99
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      (177)
    • 2 colors
      Extended Widths
      Timberland Men's 6" Premium Waterproof Boot
      Everyday Value
      $189.98
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      (509)
    • Extended Widths
      Timberland Men's 6" Boot, Created for Macy's
      LAST ACT
      $190.00
      Now $94.93
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    • 2 colors
      Steve Madden Men's Jonnie Boots, Created for Macy's
      Limited-Time Special
      $110.00
      Sale $79.99
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      (34)
    • 2 colors
      Extended Widths
      Timberland Men's Maddsen Waterproof Hiking Boots
      Limited-Time Special
      $120.00
      Sale $99.99
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      (323)
    • 2 colors
      Florsheim Men's Beat Plain-Toe Chelsea Gore Boots
      Limited-Time Special
      $130.00
      Sale $77.99
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      (48)
    • Extended Widths
      Timberland Men's 6" Basic Waterproof Boot
      Limited-Time Special
      $145.00
      Sale $109.99
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      (345)
    • Timberland Men's 6" Premium Fabric Boots
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      $150.00
      Now $74.93
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      (1)
    • Extended Widths
      Clarks Men's Bushacre 2 Chukka Boot
      Limited-Time Special
      $100.00
      Sale $69.99
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      (122)
    • 3 colors
      Johnston & Murphy Copeland Chukka Boots
      $159.00
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      (30)
    • 2 colors
      Stacy Adams Men's Alomar Cap-Toe Chelsea Boots
      Limited-Time Special
      $105.00
      Sale $72.99
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      (39)
    • Extended Widths
      Kenneth Cole Reaction Desert Sun Leather Chukka Boots
      Limited-Time Special
      $98.00
      Sale $48.99
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      (62)
    • Clarks Men's Hinman Mid-High Boots
      Limited-Time Special
      $100.00
      Sale $69.99
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      (4)
    • Extended Widths
      Timberland Men's Earthkeeper Original 6" Boot
      Everyday Value
      $149.98
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      (388)
    • G. H. Bass & Co. Men's Bennett Chukka Boots
      Limited-Time Special
      $110.00
      Sale $81.99
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      (1)
    • Extended Widths
      Rockport Men's Classic Break Chukka Boot
      Limited-Time Special
      $135.00
      Sale $80.99
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      (32)
    • Calvin Klein Men's Bain Saffiano Chukka Boots
      Limited-Time Special
      $115.00
      Sale $68.99
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      (3)
    • HUGO Men's Dress Appeal Zip Boots
      $295.00
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      (1)
    • Florsheim Men's Streets Wingtip Chelsea Gore Boots
      $130.00
      Now $84.50
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      With offer $67.60
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      (1)
    • 2 colors
      Extended Widths
      Clarks Men's Stinson Hi Top Wallabee Boots
      $110.00
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      (35)
    • Frye Men's Scott Chelsea Harness Boots Created for Macy's
      LAST ACT
      $228.00
      Now $113.93
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      (2)
    • Unlisted by Kenneth Cole Men's Roll With It Boots
      LAST ACT
      $75.00
      Now $37.43
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      (53)
    • 2 colors
      Extended Widths
      Florsheim Men's Duke Bike Toe Ankle Boot
      $135.00
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      (291)
    • 3 colors
      Extended Widths
      Stacy Adams Men's Madison Boot
      $135.00
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      (164)
    • Frye Men's Scott Chukka Boots, Created for Macy's
      Limited-Time Special
      $228.00
      Sale $158.99
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    • Tommy Hilfiger Men's Casey Waterproof Duck Boots Created for Macy's
      Limited-Time Special
      $90.00
      Sale $44.99
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      (73)
    • 5 colors
      Extended Widths
      Eastland Men's Lumber Up Boot
      Limited-Time Special
      $125.00 - 130.00
      Sale $111.99 - 116.99
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      (14)