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  • 206 items in Gray Most Comfortable Shoes

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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)
    • 4 colors
      Cole Haan Men's Zerogrand StitchLite Oxfords
      $180.00
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    • 3 colors
      Cole Haan Men's Pinch Weekender Slip-Ons
      Limited-Time Special
      $90.00
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    • 2 colors
      Cole Haan Men's Grand Horizon Oxfords
      $250.00
      Now $162.50
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      With offer $130.00
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      (2)
    • 4 colors
      Bar III Men's Finch Espadrilles, Created for Macy's
      Limited-Time Special
      $79.99
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    • 2 colors
      Extended Widths
      Kenneth Cole Reaction Desert Sun Suede Chukkas
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      $98.00
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      (150)
    • Nike Toddler Boys' Roshe One Casual Sneakers from Finish Line
      $47.99
      Now $24.98
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      (28)
    • 4 colors
      Stacy Adams Men's Percy Braided Strap Drivers
      Limited-Time Special
      $60.00
      Sale $35.99
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    • 3 colors
      Alfani Men's Varick Comfort FLX Textured Knit Oxfords, Created for Macy's
      Limited-Time Special
      $89.99
      Sale $44.99
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    • adidas Big Boys' Originals Pharrell Williams Tennis HU Casual Sneakers from Finish Line
      $89.99
      Now $59.98
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      (3)
    • 2 colors
      Kenneth Cole Reaction Men's Klay Oxfords
      Limited-Time Special
      $125.00
      Sale $74.99
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      (3)
    • 3 colors
      Frye Men's Harris Venetian Leather Loafers, Created for Macy's
      Limited-Time Special
      $158.00
      Sale $109.99
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      (1)
    • 3 colors
      Steve Madden Men's Surfari Slip-On Sneakers
      Limited-Time Special
      $70.00
      Sale $41.99
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      (2)
    • adidas Toddler Girls' X-PLR Casual Athletic Sneakers from Finish Line
      $49.99
      Now $29.98
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      (4)
    • adidas Toddler Boys' Tubular Shadow Casual Sneakers from Finish Line
      $49.99
      Now $29.98
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      (2)
    • adidas Little Boys' Tubular Shadow Casual Sneakers from Finish Line
      $59.99
      Now $39.98
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      (2)
    • 2 colors
      GUESS Men's Fusto Low-Top Sneakers
      Limited-Time Special
      $70.00
      Sale $34.99
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    • 2 colors
      Stacy Adams Men's Northpoint Moc Toe Slip-On Loafers
      Limited-Time Special
      $60.00
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      (17)
    • 3 colors
      Johnston & Murphy Men's Walden Blucher Lace-Up Oxfords
      $129.00
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      (1)
    • 3 colors
      Frye Men's Patton Slip-On Shoes, Created for Macy's
      Limited-Time Special
      $158.00
      Sale $109.99
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