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  • Sonoma Goods For Life® Ledger Men's Chukka Boots
    $34.99 sale
    $59.99 Reg.

    Sonoma Goods For Life® Ledger Men's Chukka Boots

    (131)
    Black Brown
  • Skechers Relaxed Fit® Respected Boswell Men's Boots
    $100.00

    Skechers Relaxed Fit® Respected Boswell Men's Boots

    (505)
    Dark Brown Black
  • Vance Co. Franco Men's Plain Toe Chukka Boots
    $59.49 sale
    $84.99 Reg.

    Vance Co. Franco Men's Plain Toe Chukka Boots

    (42)
    Black Brown Charcoal Coffee
  • Lugz Convoy Men's Hiking Boots
    $54.99 sale
    $74.99 Reg.

    Lugz Convoy Men's Hiking Boots

    (139)
    Black Golden Wheat Bark Tan Mars Red Gum Black Charcoal Charcoal Gum
  • Deer Stags Bangor Men's Chukka Boots
    $54.99 sale
    $60.00 Reg.

    Deer Stags Bangor Men's Chukka Boots

    (37)
    Black Redwood
  • Lugz Fringe Men's Ankle Boots
    $50.99 sale
    $59.99 Reg.

    Lugz Fringe Men's Ankle Boots

    (164)
    Yellow Black Gum Mushroom Gum Cream Golden Wheat White Black White Mars Red Gum
  • Nunn Bush® Otto Men's Leather Plain Toe Chukka Boots
    $87.99 sale
    $110.00 Reg.

    Nunn Bush® Otto Men's Leather Plain Toe Chukka Boots

    (6)
    Black Tumbled Brown Ch
  • Thomas & Vine Booker Men's Leather Plain Toe Chukka Boots
    $111.99 sale
    $159.99 Reg.

    Thomas & Vine Booker Men's Leather Plain Toe Chukka Boots

    (6)
    Cognac Black
  • Lugz Drifter Peacoat Men's Chukka Boots
    $44.99 sale
    $59.99 Reg.

    Lugz Drifter Peacoat Men's Chukka Boots

    (144)
    Black Gum Black Black Black
  • Lugz Rapid Men's Sneakers
    $44.99 sale
    $59.99 Reg.

    Lugz Rapid Men's Sneakers

    (57)
    Black Black Golden Wheat Bark Gum Brown Olive
  • Nunn Bush® Luxor Men's Waterproof Leather Ankle Boots
    $91.99 sale
    $115.00 Reg.

    Nunn Bush® Luxor Men's Waterproof Leather Ankle Boots

    (70)
    Charcoal Tan Multi
  • Nunn Bush® Circuit Men's Chukka Boots
    $62.99 - $67.99 sale
    $85.00 Reg.

    Nunn Bush® Circuit Men's Chukka Boots

    (32)
    Black Cognac
  • Lugz Convoy Men's Scuff-Proof Ankle Boots
    $54.99 sale
    $64.99 Reg.

    Lugz Convoy Men's Scuff-Proof Ankle Boots

    (114)
  • Lugz Drifter LX Men's Water Resistant Ankle Boots
    $67.99 sale
    $79.99 Reg.

    Lugz Drifter LX Men's Water Resistant Ankle Boots

    (37)
  • Propet Findley Men's Suede Chukka Boots
    $96.99 sale
    $114.95 Reg.

    Propet Findley Men's Suede Chukka Boots

    (40)
    Brown Black Gray Desert Camel
  • Nunn Bush® Odell Men's Wingtip Dress Boots
    $87.99 - $110.00
    $110.00 - $115.00 Reg.

    Nunn Bush® Odell Men's Wingtip Dress Boots

    (39)
    Tan Black Dark Brown Rust
  • Vance Co. Vaughn Men's Chukka Boots
    $83.99 sale
    $119.99 Reg.

    Vance Co. Vaughn Men's Chukka Boots

    (4)
    Gray Black Brown
  • Rocky TMC Postal Approved Duty Men's Chukka Work Boots
    $163.00

    Rocky TMC Postal Approved Duty Men's Chukka Work Boots

    (105)
  • Thomas & Vine Wilcox Men's Tru Comfort Foam Leather Chukka Boots
    $153.99 sale
    $219.99 Reg.

    Thomas & Vine Wilcox Men's Tru Comfort Foam Leather Chukka Boots

    (6)
    Black Brown
  • Nunn Bush® Excavate Men's Plain Toe Ankle Boots
    $71.99 sale
    $90.00 Reg.

    Nunn Bush® Excavate Men's Plain Toe Ankle Boots

    (3)
    Black Tan Multi Brown
  • Thomas & Vine Keegan Men's Chukka Boots
    $104.99 sale
    $149.99 Reg.

    Thomas & Vine Keegan Men's Chukka Boots

    (3)
    Taupe Cognac Black
  • Nunn Bush® Ozark Men’s Plain Toe Dress Chukka Boots
    $91.99 sale
    $115.00 Reg.

    Nunn Bush® Ozark Men’s Plain Toe Dress Chukka Boots

    (15)
  • Vance Co. Redford Chukka Men's Ankle Boot
    $83.99 sale
    $119.99 Reg.

    Vance Co. Redford Chukka Men's Ankle Boot

    (1)
    Black Tan Brown
  • Vance Co. Austin Men's Chukka Boots
    $62.99 sale
    $89.99 Reg.

    Vance Co. Austin Men's Chukka Boots

    (13)
    Tan Gray Navy Black
  • Lugz Colorado Men's Ankle Boots
    $64.99 sale
    $84.99 Reg.

    Lugz Colorado Men's Ankle Boots

    (29)
    Black Brown Golden Wheat Bark Gum
  • Vance Co. Arturo Tru Comfort Foam Men's Chukka Boots
    $90.99 sale
    $129.99 Reg.

    Vance Co. Arturo Tru Comfort Foam Men's Chukka Boots

    Black Brown Cognac
  • Vance Co. Linus Men's Tru Comfort Foam Chukka Boots
    $90.99 sale
    $129.99 Reg.

    Vance Co. Linus Men's Tru Comfort Foam Chukka Boots

    (3)
    Brown Black Cognac
  • Eastland Cyrus Men's Chelsea Boots
    $71.99 sale
    $90.00 Reg.

    Eastland Cyrus Men's Chelsea Boots

    (4)
    Black Brown Nutmeg
  • Dockers® Dartford Men's Boots
    $63.75 sale
    $85.00 Reg.

    Dockers® Dartford Men's Boots

    (2)
    Dark Brown Black Tan
  • Thomas & Vine Avrum Cap Toe Men's Leather Ankle Boots
    $139.99 sale
    $199.99 Reg.

    Thomas & Vine Avrum Cap Toe Men's Leather Ankle Boots

    (6)
    Cognac Black Bordeaux
  • Thomas & Vine Mitchell Men's Leather Ankle Boots
    $111.99 sale
    $159.99 Reg.

    Thomas & Vine Mitchell Men's Leather Ankle Boots

    (5)
    Cognac Black
  • Thomas & Vine Aldridge Men's Leather Chukka Boots
    $115.49 sale
    $164.99 Reg.

    Thomas & Vine Aldridge Men's Leather Chukka Boots

    (6)
    Cognac Black
  • Thomas & Vine Theo Men's Chukka Boots
    $97.99 sale
    $139.99 Reg.

    Thomas & Vine Theo Men's Chukka Boots

    (3)
    Black Brown
  • Levi's® Joshua Men's Chukka Boots
    $59.99

    Levi's® Joshua Men's Chukka Boots

    (1)
    Black Mono Wheat Gray Mono
  • Eastland Finn Men's Chukka Boots
    $71.99 sale
    $90.00 Reg.

    Eastland Finn Men's Chukka Boots

    (3)
  • Rocky Postal TMC Men's Water Resistant Work Boots
    $178.00

    Rocky Postal TMC Men's Water Resistant Work Boots

    (17)
  • Stacy Adams Corbin Men's Suede Chukka Boots
    $71.99 sale
    $79.99 Reg.

    Stacy Adams Corbin Men's Suede Chukka Boots

    (3)
    Black Brown Cognac
  • Thomas & Vine Cutler Men's Leather Chukka Boots
    $111.99 sale
    $159.99 Reg.

    Thomas & Vine Cutler Men's Leather Chukka Boots

    (7)
  • Levi's® Daleside Men's Chukka Boots
    $100.00

    Levi's® Daleside Men's Chukka Boots

    (3)
  • Lugz Rapid Men's Ankle Boots
    $54.99 sale
    $69.99 Reg.

    Lugz Rapid Men's Ankle Boots

    (3)
  • Nunn Bush® Chase Men's Boots
    $71.99 sale
    $90.00 Reg.

    Nunn Bush® Chase Men's Boots

    (1)
    Brandy Cognac Multi Black
  • Dr. Scholl's Graham Men's Chelsea Boots
    $105.00 sale
    $140.00 Reg.

    Dr. Scholl's Graham Men's Chelsea Boots

    (3)
    Black Synthetic Chestnut Brown
  • Lugz Mantle Mid Men's Ankle Boots
    $71.99 sale
    $84.99 Reg.

    Lugz Mantle Mid Men's Ankle Boots

    (98)
    Yellow Black Dk Brown Falcon Black
  • Lugz Diablo Hi Men's Fleece-Lined Hiking Boots
    $71.99 sale
    $84.99 Reg.

    Lugz Diablo Hi Men's Fleece-Lined Hiking Boots

    (13)
    Black Forged Iron Chocolate Caribou Charcoal Alloy Black
  • Best Seller
    Sonoma Goods For Life® Aaron Men's Chukka Boots
    $25.49 with code GOSHOP15 Promo details.
    $29.99 clearance $59.99 Reg.

    Sonoma Goods For Life® Aaron Men's Chukka Boots

    (835)
    Closeout Deal
  • Lugz Scaffold Men's Chukka Boots
    $62.99 sale
    $74.99 Reg.

    Lugz Scaffold Men's Chukka Boots

    (3)
  • Eastland Seth Men's Ankle Boots
    $71.99 sale
    $90.00 Reg.

    Eastland Seth Men's Ankle Boots

    (8)
  • Nunn Bush® Denali Men's Waterproof Chukka Boots
    $115.00

    Nunn Bush® Denali Men's Waterproof Chukka Boots

    (48)