Shop Men's Chukka Boots

42 Total Items

42 Total Items

Men's Freeman Brent Chukka Boots in Tan color
Freeman
$79.99
$69.98

Men's Freeman Brent Chukka Boots

$79.99
$69.98
Men's TWISTED X Original Chukka Driving Moc Dress Shoes in Bomber color
TWISTED X
$139.99
$129.98

Men's TWISTED X Original Chukka Driving Moc Dress Shoes

$139.99
$129.98
Men's Reserved Footwear Keith Dress Shoes in Grey color
Reserved Footwear
$64.99
$54.98

Men's Reserved Footwear Keith Dress Shoes

$64.99
$54.98
Men's Reserved Footwear Keith Dress Shoes in Black color
Reserved Footwear
$64.99
$54.98

Men's Reserved Footwear Keith Dress Shoes

$64.99
$54.98
Men's Reserved Footwear Keith Dress Shoes in Cognac color
Reserved Footwear
$64.99
$54.98

Men's Reserved Footwear Keith Dress Shoes

$64.99
$54.98
Men's Vintage Foundry Co Milton Chukka Dress Boots in Brown color
Vintage Foundry Co
$149.99
$114.98

Men's Vintage Foundry Co Milton Chukka Dress Boots

$149.99
$114.98
Men's Vintage Foundry Co Milton Chukka Dress Boots in Navy color
Vintage Foundry Co
$149.99
$114.98

Men's Vintage Foundry Co Milton Chukka Dress Boots

$149.99
$114.98
Men's Carhartt Haslett Moc Toe Canvas Chukka Work Boots in Brown color
Carhartt
$104.99

Men's Carhartt Haslett Moc Toe Canvas Chukka Work Boots

$104.99
Men's Carhartt Haslett Moc Toe Canvas Chukka Work Boots in Coyote color
Carhartt
$104.99

Men's Carhartt Haslett Moc Toe Canvas Chukka Work Boots

$104.99
Men's Carhartt Haslett Moc Toe Canvas Chukka Work Boots in Black color
Carhartt
$104.99

Men's Carhartt Haslett Moc Toe Canvas Chukka Work Boots

$104.99
Men's Vintage Foundry Co Marlow Chukka Dress Boots in Black color
Vintage Foundry Co
$149.99
$114.98

Men's Vintage Foundry Co Marlow Chukka Dress Boots

$149.99
$114.98
Men's Vintage Foundry Co Marlow Chukka Dress Boots in Brown color
Vintage Foundry Co
$149.99
$114.98

Men's Vintage Foundry Co Marlow Chukka Dress Boots

$149.99
$114.98
Men's Thomas & Vine Banks Chukka Boots in Cognac color
Thomas & Vine
$189.99
$69.98

Men's Thomas & Vine Banks Chukka Boots

$189.99
$69.98
Men's Thomas & Vine Banks Chukka Boots in Charcoal color
Thomas & Vine
$189.99
$69.98

Men's Thomas & Vine Banks Chukka Boots

$189.99
$69.98
Men's Eastland Jack Chukka Boots in Oak color
Eastland
$139.99

Men's Eastland Jack Chukka Boots

$139.99
Men's Eastland Jack Chukka Boots in Peanut color
Eastland
$124.99

Men's Eastland Jack Chukka Boots

$124.99
Men's Territory Redwoods Chukka Boots in Grey color
Territory
$159.99
$59.98

Men's Territory Redwoods Chukka Boots

$159.99
$59.98
Men's Territory Redwoods Chukka Boots in Brown color
Territory
$159.99
$59.98

Men's Territory Redwoods Chukka Boots

$159.99
$59.98
Men's Rockport Classic Break Chukka Dress Boots in Dark Brown color
Rockport
$139.99

Men's Rockport Classic Break Chukka Dress Boots

$139.99
Men's Nunn Bush Otto Plain Toe Chukka Boots in Navy color
Nunn Bush
$94.99
$79.98

Men's Nunn Bush Otto Plain Toe Chukka Boots

$94.99
$79.98
Men's Nunn Bush Otto Plain Toe Chukka Boots in Brown CH color
Nunn Bush
$109.99
$84.98

Men's Nunn Bush Otto Plain Toe Chukka Boots

$109.99
$84.98
Men's Nunn Bush Otto Plain Toe Chukka Boots in Gray color
Nunn Bush
$94.99
$79.98

Men's Nunn Bush Otto Plain Toe Chukka Boots

$94.99
$79.98
Men's Thomas & Vine Theo Dress Boots in Brown color
Thomas & Vine
$139.99
$54.98

Men's Thomas & Vine Theo Dress Boots

$139.99
$54.98
Men's Thomas & Vine Theo Dress Boots in Black color
Thomas & Vine
$139.99
$54.98

Men's Thomas & Vine Theo Dress Boots

$139.99
$54.98