Macy's Presents: The Edit- A curated mix of fashion and inspiration Check It Out
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  • 48 items in Brown Mens Winter Shoes

                    
                
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    • 4 colors
      Extended Widths
      Clarks Men's Bushacre 2 Chukka Boots
      Limited-Time Special
      $100.00
      Sale $69.99
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      (23)
    • 2 colors
      Extended Widths
      Steve Madden Harken Chukka Boots
      Limited-Time Special
      $90.00
      Sale $79.99
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      (179)
    • 2 colors
      Extended Widths
      Timberland Men's Mt. Maddsen Waterproof Hiking Boots
      Limited-Time Special
      $120.00
      Sale $99.99
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      (341)
    • Extended Widths
      Timberland Men's Earthkeeper Original 6" Boot
      Everyday Value
      $149.98
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      (396)
    • 2 colors
      Stacy Adams Men's Alomar Cap-Toe Chelsea Boots
      Limited-Time Special
      $105.00
      Sale $72.99
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      (41)
    • Alfani Jack Cap Toe Boots, Created for Macy's
      Limited-Time Special
      $99.99
      Sale $63.99
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      (65)
    • UGG® Men's Freamon Leather Chukka Boots
      $150.00
      Now $97.50
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    • 2 colors
      Florsheim Men's Beat Plain-Toe Chelsea Gore Boots
      $130.00
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      (48)
    • Clarks Men's Hinman Mid-High Boots
      Limited-Time Special
      $100.00
      Sale $69.99
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      (4)
    • 3 colors
      Extended Widths
      Stacy Adams Men's Madison Boot
      $135.00
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      (221)
    • Extended Widths
      Kenneth Cole Reaction Desert Sun Leather Chukka Boots
      Limited-Time Special
      $98.00
      Sale $67.99
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      (62)
    • Frye Men's Scott Chukka Boots, Created for Macy's
      $228.00
      Now $148.20
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      New markdown
      Prices just reduced - Limited Quantities
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    • 3 colors
      Alfani Men's Aiden Chukka Boot Created for Macy's
      Limited-Time Special
      $59.99
      Sale $37.99
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      (17)
    • Unlisted by Kenneth Cole Men's Roll With It Boots
      LAST ACT
      $75.00
      Now $37.43
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      Last Act: Extra savings do not apply
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      (53)
    • 5 colors
      Extended Widths
      Eastland Men's Lumber Up Boot
      Limited-Time Special
      $125.00 - 130.00
      Sale $109.99
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      (14)
    • Extended Widths
      Rockport Men's Classic Break Chukka Boot
      $135.00
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      (32)
    • 2 colors
      Tommy Hilfiger Men's Gervis Chukka Boots
      $90.00
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      (7)
    • Alfani Men's Jason Lace-Up Boots, Created for Macy's
      $99.99
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      (10)
    • UGG® Men's Yucca Waterproof Boots
      $120.00
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      (48)
    • 3 colors
      G.H. Bass & Co. Men's Buck 2.0 Demi Boots
      Limited-Time Special
      $135.00
      Sale $93.99
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      (2)
    • 8 colors
      Extended Widths
      Eastland Men's Seneca Boot
      Limited-Time Special