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  • 466 items in Black Most Comfortable Shoes

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    • 3 colors
      Cole Haan Men's Original Grand Wing Oxfords
      $150.00
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    • 5 colors
      Calvin Klein Men's Aggussie Nylon Oxfords
      Limited-Time Special
      $130.00
      Sale $64.99
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      (9)
    • 2 colors
      Extended Widths
      Clarks Men's Cotrell Step Bike Toe Slip On
      Limited-Time Special
      $90.00
      Sale $62.99
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      (127)
    • 4 colors
      Cole Haan Men's Zerogrand StitchLite Oxfords
      $180.00
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    • 2 colors
      Lightweight
      Rockport Men’s Style Leader 2 Bike Toe Slip On Loafers
      Limited-Time Special
      $110.00
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      (84)
    • 4 colors
      Alfani Men's Sawyer Slip-On Loafers, Created for Macy's
      LAST ACT select colors
      $79.99
      Sale $39.93 - 39.99
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      (39)
    • Extended Widths
      Rockport Men's Waterproof Northfield Oxford
      Limited-Time Special
      $110.00
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      (525)
    • 3 colors
      Cole Haan Men's Pinch Weekender Slip-Ons
      Limited-Time Special
      $90.00
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    • 2 colors
      Extended Widths
      Clarks Men's Cotrell Edge Oxfords
      Limited-Time Special
      $90.00
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      (130)
    • 2 colors
      Extended Widths
      Timberland Men's 6" Premium Waterproof Boot
      Everyday Value
      $189.98
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      (506)
    • 2 colors
      Ecco Men's Soft 7 Retro Sneakers
      $120.00
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      (19)
    • 2 colors
      Extended Widths
      Steve Madden Harken Chukka Boots
      Limited-Time Special
      $90.00
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      (177)
    • 2 colors
      Extended Widths
      Clarks Men's Cotrell Walk Sneaker
      Limited-Time Special
      $90.00
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      (103)
    • 3 colors
      Florsheim Men's Verge Double Gore Slip-on Sneakers, Created for Macy's
      Limited-Time Special
      $80.00
      Sale $47.99
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      (6)
    • adidas Little Boys' N-5923 Casual Sneakers from Finish Line
      $54.99
      Now $34.98
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      (3)