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  • 33 items in Boots Most Comfortable Shoes

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    • 5 colors
      Extended Widths
      Clarks Men's Bushacre 2 Chukka Boots
      Limited-Time Special
      $100.00
      Sale $69.99
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      (22)
    • 2 colors
      Extended Widths
      Steve Madden Harken Chukka Boots
      Limited-Time Special
      $90.00
      Sale $69.99
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      (177)
    • 2 colors
      Extended Widths
      Timberland Men's 6" Premium Waterproof Boot
      Everyday Value
      $189.98
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      (508)
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      Timberland Men's 6" Boot, Created for Macy's
      $190.00
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      (153)
    • 2 colors
      Extended Widths
      Kenneth Cole Reaction Desert Sun Suede Chukkas
      Limited-Time Special
      $98.00
      Sale $48.99
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      (150)
    • Extended Widths
      Timberland Men's 6" Basic Waterproof Boot
      Limited-Time Special
      $145.00
      Sale $109.99
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      (345)
    • Extended Widths
      Clarks Men's Bushacre 2 Chukka Boot
      Limited-Time Special
      $100.00
      Sale $69.99
      Free ship at $49
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      (122)
    • 3 colors
      Johnston & Murphy Copeland Chukka Boots
      $159.00
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      (30)
    • Extended Widths
      Kenneth Cole Reaction Desert Sun Leather Chukka Boots
      Limited-Time Special
      $98.00
      Sale $48.99
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      (62)
    • Extended Widths
      Timberland Men's Earthkeeper Original 6" Boot
      Everyday Value
      $149.98
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      (387)
    • Extended Widths
      Rockport Men's Classic Break Chukka Boot
      Limited-Time Special
      $135.00
      Sale $80.99
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      (32)
    • 2 colors
      Extended Widths
      Clarks Men's Stinson Hi Top Wallabee Boots
      $110.00
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      (35)
    • Frye Men's Scott Chelsea Harness Boots Created for Macy's
      LAST ACT
      $228.00
      Now $113.93
      coupon excluded
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      (2)
    • 5 colors
      Extended Widths
      Eastland Men's Lumber Up Boot
      Limited-Time Special
      $125.00 - 130.00
      Sale $111.99 - 116.99
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      (14)
    • Timberland Men's Kendrick Chelsea Boots
      $140.00
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      (14)
    • 3 colors
      Clarks Men's Original Desert Boots
      $130.00
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      (202)
    • Extended Widths
      Kenneth Cole Reaction Desert Sun Leather Chukka Boots
      $98.00
      Now $63.70
      Extra 20% off use: SHOP
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      With offer $50.96
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      (2)
    • 9 colors
      Extended Widths
      Eastland Men's Seneca Boot
      Limited-Time Special
      $110.00
      Sale $81.99
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      (6)
    • Kenneth Cole Reaction Desert Sun Suede Chukkas
      $98.00
      Now $63.70
      Extra 20% off use: SHOP
      Extra 20% off select merchandise!
      Extra 20% off use: SHOP
      With offer $50.96
      New markdown
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      (20)
    • UGG® Men's Neumel Classic Boots
      $130.00
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      (2074)
    • Crocs Handle It Rain Boots, Toddler Girls & Little Girls
      $35.00
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      (423)
    • Crocs Handle It Rain Boots, Toddler Boys & Little Boys
      $34.99
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      (423)
    • UGG® Men's Yucca Waterproof Boots
      $120.00
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      (48)
    • Frye Men's Scott Chelsea Harness Boots Created for Macy's
      LAST ACT
      $228.00
      Now $113.93
      coupon excluded
      Last Act: Extra savings do not apply
      coupon excluded
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      (4)
    • Carter's Cata Fringe Boots, Toddler & Little Girls
      LAST ACT
      $44.00
      Now $17.53
      coupon excluded
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      coupon excluded
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    • BEARPAW Boo Youth Boots, Little Girls & Big Girls
      $79.99
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      While Supplies Last.
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      (1)
    • Extended Widths