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  • 66 items in

    Chukkas 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
      BONUS BUY WITH PURCHASE
      $29.99 Diamond Pendant with any $25 purchase.
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      (41)
    • 2 colors
      Bar III Men's Allan Chelsea Boots, Created for Macy's
      Limited-Time Special
      $109.99
      Sale $65.99
      BONUS BUY WITH PURCHASE
      $29.99 Diamond Pendant with any $25 purchase.
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      (8)
    • 3 colors
      Kenneth Cole Reaction Men's Passage Suede Boots
      Limited-Time Special
      $98.00
      Sale $29.99
      BONUS BUY WITH PURCHASE
      $29.99 Diamond Pendant with any $25 purchase.
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      (7)
    • 3 colors
      Clarks Men's Vargo Apron-Toe Leather Chukka Boots, Created for Macy's
      Limited-Time Special
      $110.00
      Sale $76.99
      BONUS BUY WITH PURCHASE
      $29.99 Diamond Pendant with any $25 purchase.
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      (36)
    • 3 colors
      Calvin Klein Men's Ultan Suede Chukka Boots
      $150.00
      Now $74.92
      Extra 15% off code: PRES
      Extra 15% off select merchandise!
      Extra 15% off code: PRES Extra 15% off code: PRES
      With offer $63.68
      BONUS BUY WITH PURCHASE
      $29.99 Diamond Pendant with any $25 purchase.
      BONUS BUY WITH PURCHASE BONUS BUY WITH PURCHASE
      (4)
    • 2 colors
      Tommy Hilfiger Men's Gervis Chukka Boots
      Limited-Time Special
      $90.00
      Sale $49.99
      BONUS BUY WITH PURCHASE
      $29.99 Diamond Pendant with any $25 purchase.
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      (20)
    • UGG® Men's Neumel Classic Boots
      $130.00
      BONUS BUY WITH PURCHASE
      $29.99 Diamond Pendant with any $25 purchase.
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      (2088)
    • 2 colors
      Extended Widths
      Steve Madden Harken Chukka Boots
      Limited-Time Special
      $90.00
      Sale $62.99
      BONUS BUY WITH PURCHASE
      $29.99 Diamond Pendant with any $25 purchase.
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      (186)
    • Extended Widths
      Clarks Men's Stinson Hi Top Wallabee Boots
      $100.00
      Now $75.00
      Extra 15% off code: PRES
      Extra 15% off select merchandise!
      Extra 15% off code: PRES Extra 15% off code: PRES
      With offer $63.75
      BONUS BUY WITH PURCHASE
      $29.99 Diamond Pendant with any $25 purchase.
      BONUS BUY WITH PURCHASE BONUS BUY WITH PURCHASE
      (2)
    • Extended Widths
      Clarks Men's Bushacre 2 Chukka Boot
      Limited-Time Special
      $100.00
      Sale $69.99
      BONUS BUY WITH PURCHASE
      $29.99 Diamond Pendant with any $25 purchase.
      BONUS BUY WITH PURCHASE BONUS BUY WITH PURCHASE
      Free ship at $49
      Enjoy Free Shipping at $49! See exclusions.
      Free ship at $49 Free ship at $49
      (128)
    • 2 colors
      Timberland Men's Richdale Leather Chukka Boots, Created For Macy's
      Limited-Time Special
      $140.00
      Sale $99.99
      BONUS BUY WITH PURCHASE
      $29.99 Diamond Pendant with any $25 purchase.
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      (4)
    • Clarks Men's Tilden Top Waterproof Dress Chukka Boots
      Limited-Time Special
      $115.00
      Sale $79.99
      BONUS BUY WITH PURCHASE
      $29.99 Diamond Pendant with any $25 purchase.
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      Free ship at $49
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      (2)
    • 3 colors
      Johnston & Murphy Copeland Chukka Boots
      $159.00
      BONUS BUY WITH PURCHASE
      $29.99 Diamond Pendant with any $25 purchase.
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      (33)
    • Kenneth Cole Reaction Men's Passage Boots
      Limited-Time Special
      $98.00
      Sale $38.99
      BONUS BUY WITH PURCHASE
      $29.99 Diamond Pendant with any $25 purchase.
      BONUS BUY WITH PURCHASE BONUS BUY WITH PURCHASE
      Free ship at $49
      Enjoy Free Shipping at $49! See exclusions.
      Free ship at $49 Free ship at $49
    • UGG® Men's Neumel Chukka Boots
      $150.00
      BONUS BUY WITH PURCHASE
      $29.99 Diamond Pendant with any $25 purchase.
      BONUS BUY WITH PURCHASE BONUS BUY WITH PURCHASE
      Free ship at $49
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      Free ship at $49 Free ship at $49
      (18)
    • Unlisted by Kenneth Cole Men's Russell Boots
      Limited-Time Special
      $95.00
      Sale $46.99
      BONUS BUY WITH PURCHASE
      $29.99 Diamond Pendant with any $25 purchase.
      BONUS BUY WITH PURCHASE BONUS BUY WITH PURCHASE
      Free ship at $49
      Enjoy Free Shipping at $49! See exclusions.
      Free ship at $49 Free ship at $49
      (3)
    • Kenneth Cole Men's Aaron Leather Zip Boots
      Limited-Time Special
      $175.00
      Sale $69.99
      BONUS BUY WITH PURCHASE
      $29.99 Diamond Pendant with any $25 purchase.
      BONUS BUY WITH PURCHASE BONUS BUY WITH PURCHASE
      Free ship at $49
      Enjoy Free Shipping at $49! See exclusions.
      Free ship at $49 Free ship at $49
    • Alfani Men's Jason Wool Boots, Created for Macy's
      Limited-Time Special
      $99.99
      Sale $29.99
      BONUS BUY WITH PURCHASE
      $29.99 Diamond Pendant with any $25 purchase.
      BONUS BUY WITH PURCHASE BONUS BUY WITH PURCHASE
      Free ship at $49