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  • 590 items in Men Most Comfortable Shoes

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    • 2 colors
      Tommy Hilfiger Men's Axtons Drivers, Created For Macy's
      Black Friday Special
      $70.00
      Sale $39.99
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      Bonus Value $200
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      (14)
    • 4 colors
      Extended Widths
      Clarks Men's Bushacre 2 Chukka Boots
      Black Friday Special
      $100.00
      Sale $59.99
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      (22)
    • 2 colors
      Cole Haan Men's Original Grand Wing Oxfords
      $150.00
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      (36)
    • 5 colors
      Calvin Klein Men's Aggussie Nylon Oxfords
      Black Friday Special
      $130.00
      Sale $64.99
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      (11)
    • 4 colors
      Cole Haan Men's Zerogrand StitchLite Oxfords
      $180.00
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      (84)
    • Extended Widths
      Timberland Men's 6" Boot, Created for Macy's
      LAST ACT
      $190.00
      Now $94.93
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      (2)
    • 2 colors
      Extended Widths
      Clarks Men's Cotrell Step Bike Toe Slip On
      Black Friday Special
      $90.00
      Sale $53.99
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      (129)
    • 2 colors
      Lightweight
      Rockport Men’s Style Leader 2 Bike Toe Slip On Loafers
      Black Friday Special
      $110.00
      Sale $76.99
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      (88)
    • 3 colors
      Cole Haan Men's Pinch Weekender Slip-Ons
      Black Friday Special
      $90.00
      Sale $80.99
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      (8)
    • Extended Widths
      Rockport Men's Waterproof Northfield Oxford
      Black Friday Special
      $110.00
      Sale $76.99
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      Bonus Value $200
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      (535)
    • 2 colors
      Alfani Men's Sawyer Slip-On Loafers, Created for Macy's
      LAST ACT
      $79.99
      Now $39.93
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    • 3 colors
      Timberland Men's Piper Cove Leather Boat Shoes
      Black Friday Special
      $100.00
      Sale $69.99
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      Bonus Value $200
      24.99 with any purchase. Available at checkout
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      (83)
    • 2 colors
      Extended Widths