Shop Men's Winter Chelsea Boots

Sponsored
About our ads
$199.00
8000Kicks - The Crossover Hemp Chelsea Boots For Men In Full Black, M10 | EU 44
8000Kicks
Free shipping
$199.00
8000Kicks - The Crossover Hemp Chelsea Boots For Men In Full Black, M10 | EU 44
8000Kicks
Free shipping
$199.00
8000Kicks - The Crossover Hemp Chelsea Boots For Men In Black, M14 | EU 48
8000Kicks
Free shipping
$199.00
8000Kicks - The Crossover Hemp Chelsea Boots For Men In Black, M14 | EU 48
8000Kicks
Free shipping
$990.00
Moncler Peak City Nubuck Chelsea Boots, Men, Brown, Size: 44
Moncler
$990.00
Moncler Peak City Nubuck Chelsea Boots, Men, Brown, Size: 44
Moncler
$149.95
Chaco Men's Fields Chelsea Waterproof Boot, Black, 10.5
Amazon.com
54
Free shipping
$149.95
Chaco Men's Fields Chelsea Waterproof Boot, Black, 10.5
Amazon.com
54
$150.00
Men's Stonington Chelsea Boots, Leather Dark Oakwood 10.5 M(D), Leather/Rubber | L.L.Bean
L.L.Bean
In store
50% Off*
Free shipping
$150.00
Men's Stonington Chelsea Boots, Leather Dark Oakwood 10.5 M(D), Leather/Rubber | L.L.Bean
L.L.Bean
50% Off*
$149.99
Carhartt Men's Wedge 5-Inch Chelsea Pullon Soft Toe fw5033m Dark Bison Oil Tanned 10.5 Wide
Amazon.com
453
Free shipping
$149.99
Carhartt Men's Wedge 5-Inch Chelsea Pullon Soft Toe fw5033m Dark Bison Oil Tanned 10.5 Wide
Amazon.com
453
$99.99
Redhead ASC IV Chelsea Insulated Waterproof Boots For Men - Brown - 9m
Cabela's
In store
$99.99
Redhead ASC IV Chelsea Insulated Waterproof Boots For Men - Brown - 9m
Cabela's
$99.76
Sperry Mens Cold Bay Chelsea
Amazon.com
3
Free shipping
$99.76
Sperry Mens Cold Bay Chelsea
Amazon.com
3
$47.99
$119.99
Men's Terrain All Weather Chelsea Boots - Lands' End - Brown - 11
Lands' End
60% off
$47.99
$119.99
Men's Terrain All Weather Chelsea Boots - Lands' End - Brown - 11
Lands' End
$129.99
Timberland Redwood Falls Chelsea Boot | Men's | Black | Size 10.5 | Boots | Lug
DSW
87
Free shipping
$129.99
Timberland Redwood Falls Chelsea Boot | Men's | Black | Size 10.5 | Boots | Lug
DSW
87
$249.95
Danner Men's Tramline Chelsea 917 GTX Waterproof Boots In Major Brown Size 10.5m
WorkBoots.com
$249.95
Danner Men's Tramline Chelsea 917 GTX Waterproof Boots In Major Brown Size 10.5m
WorkBoots.com
$144.50
$180.00
Dr. Martens 2976 Leather Chelsea Boots Boots Black : UK 9 (US Men's 10 - US Women's 11) M
Zappos
51
19% off
$144.50
$180.00
Dr. Martens 2976 Leather Chelsea Boots Boots Black : UK 9 (US Men's 10 - US Women's 11) M
Zappos
51
$249.95
Danner Men's Tramline Chelsea 917 GTX Waterproof Boots In Roasted Pecan Size 10.5m
WorkBoots.com
$249.95
Danner Men's Tramline Chelsea 917 GTX Waterproof Boots In Roasted Pecan Size 10.5m
WorkBoots.com
$129.99
Carhartt Men's Frontier Water Resistant Chelsea | Dark Brown | 10 m
Carhartt
1
$129.99
Carhartt Men's Frontier Water Resistant Chelsea | Dark Brown | 10 m
Carhartt
1
$99.99
Redhead ASC IV Chelsea Insulated Waterproof Boots For Men - Brown - 11m
Bass Pro Shops
$99.99
Redhead ASC IV Chelsea Insulated Waterproof Boots For Men - Brown - 11m
Bass Pro Shops
$249.95
Danner Men's Tramline Chelsea 917 GTX Waterproof Boots In Major Brown Size 10.5m
TacticalGear.com
$249.95
Danner Men's Tramline Chelsea 917 GTX Waterproof Boots In Major Brown Size 10.5m
TacticalGear.com
$139.99
Timberland Redwood Edge Chelsea Boot | Men's | Brown | Size 10 | Boots
DSW
In store
Free shipping
$139.99
Timberland Redwood Edge Chelsea Boot | Men's | Brown | Size 10 | Boots
DSW
Free shipping
$139.96
Frye & Co. Hank Chelsea Boot | Men's | Cognac | Size 9 | Boots
DSW
Free shipping
$139.96
Frye & Co. Hank Chelsea Boot | Men's | Cognac | Size 9 | Boots
DSW
Free shipping
$239.95
Danner Men's Bull Run Chelsea Boots In Brown Size 10.5m
WorkBoots.com
$239.95
Danner Men's Bull Run Chelsea Boots In Brown Size 10.5m
WorkBoots.com
$44.99
$100.00
St. John's Bay Mens Rutland Flat Heel Chelsea Boots | Black | Regular 11 | Boots Chelsea Boots | Memory Foam
JCPenney
In store
22
Curbside
$44.99
$100.00
St. John's Bay Mens Rutland Flat Heel Chelsea Boots | Black | Regular 11 | Boots Chelsea Boots | Memory Foam
JCPenney
22
$209.95
Men's Wexford Waterproof Chelsea Boots In Weathered Brown, Size: 11.5 D / Medium By Ariat
Ariat
308
$209.95
Men's Wexford Waterproof Chelsea Boots In Weathered Brown, Size: 11.5 D / Medium By Ariat
Ariat
308
$209.95
Men's Wexford Waterproof Chelsea Boots In Black, Size: 7 D / Medium By Ariat
Ariat
308
$209.95
Men's Wexford Waterproof Chelsea Boots In Black, Size: 7 D / Medium By Ariat
Ariat
308
$44.99
$59.99
Tamarack Men's Passage Chelsea Winter Boots In Brown, 9, Leather/Rubber
Blain's Farm & Fleet
25% off
$44.99
$59.99
Tamarack Men's Passage Chelsea Winter Boots In Brown, 9, Leather/Rubber
Blain's Farm & Fleet
$274.95
Blundstone Footwear Thermal Waterproof Genuine Shearling Lined Chelsea Boot In Antique Brown At Nordstrom, Size 8.5
Nordstrom
1
$274.95
Blundstone Footwear Thermal Waterproof Genuine Shearling Lined Chelsea Boot In Antique Brown At Nordstrom, Size 8.5
Nordstrom
1
$209.95
Men's Wexford Waterproof Chelsea Boots In Java, Size: 11 D / Medium By Ariat
Ariat
$209.95
Men's Wexford Waterproof Chelsea Boots In Java, Size: 11 D / Medium By Ariat
Ariat
$89.99
Redhead Chelsea IV Insulated Waterproof Slip-On Shoes For Men - Brown - 11m
Cabela's
In store
$89.99
Redhead Chelsea IV Insulated Waterproof Slip-On Shoes For Men - Brown - 11m
Cabela's
$249.95
Danner Men's Tramline Chelsea 917 GTX Waterproof Boots In Roasted Pecan Size 10.5m
TacticalGear.com
$249.95
Danner Men's Tramline Chelsea 917 GTX Waterproof Boots In Roasted Pecan Size 10.5m
TacticalGear.com
$299.99
$550.00
Allen Edmonds Tanner Weatherproof Chelsea Boot Boots In Grey Leather, Size 8.0 D
Allen Edmonds
45% off
$299.99
$550.00
Allen Edmonds Tanner Weatherproof Chelsea Boot Boots In Grey Leather, Size 8.0 D
Allen Edmonds
$235.00
The Men's Store At Bloomingdale's Men's Pull On Chelsea Boots - Exclusive - Brown - Size 8
Bloomingdale's
Free shipping
$235.00
The Men's Store At Bloomingdale's Men's Pull On Chelsea Boots - Exclusive - Brown - Size 8
Bloomingdale's
Free shipping
$550.00
Allen Edmonds Tanner Weatherproof Chelsea Boot Boots In Brown Chromexcel Leather, Size 10.0 D
Allen Edmonds
$550.00
Allen Edmonds Tanner Weatherproof Chelsea Boot Boots In Brown Chromexcel Leather, Size 10.0 D
Allen Edmonds
$550.00
Allen Edmonds Tanner Weatherproof Chelsea Boot Boots In Black Leather, Size 11.5 D
Allen Edmonds
$550.00
Allen Edmonds Tanner Weatherproof Chelsea Boot Boots In Black Leather, Size 11.5 D
Allen Edmonds
$209.95
Blundstone Classic Chelsea Boots Rustic Brown 8.5 Mens/10.5 Womens
REI
Free shipping
$209.95
Blundstone Classic Chelsea Boots Rustic Brown 8.5 Mens/10.5 Womens
REI
Free shipping
$165.00
Bogs Men's Arcata Urban Chelsea Snow Boots Dark Brown 13
REI
35
Free shipping
$165.00
Bogs Men's Arcata Urban Chelsea Snow Boots Dark Brown 13
REI
35
$299.99
Men's Classic Chelsea In Brown Leather 3190 | Red Wing Heritage
Red Wing
68
$299.99
Men's Classic Chelsea In Brown Leather 3190 | Red Wing Heritage
Red Wing
68
$150.00
Vans Mens Snow Boots MTE Standard Mid Chelsea Waterproof 9.5 / Faded Black (EMV)
Hansen Surfboards
$150.00
Vans Mens Snow Boots MTE Standard Mid Chelsea Waterproof 9.5 / Faded Black (EMV)
Hansen Surfboards
$199.97
To Boot New York Charleston Chelsea Boot - Black - Casual Boots Size 10
Nordstrom Rack
$199.97
To Boot New York Charleston Chelsea Boot - Black - Casual Boots Size 10
Nordstrom Rack
See more
See less
    Some results have been hidden because they may be inaccessible to you.Show inaccessible results
    See more images

    Shop Men's Winter Chelsea Boots

    Sponsored
    About our ads
    $199.00
    8000Kicks - The Crossover Hemp Chelsea Boots For Men In Full Black, M10 | EU 44
    8000Kicks
    Free shipping
    $199.00
    8000Kicks - The Crossover Hemp Chelsea Boots For Men In Full Black, M10 | EU 44
    8000Kicks
    Free shipping
    $199.00
    8000Kicks - The Crossover Hemp Chelsea Boots For Men In Black, M14 | EU 48
    8000Kicks
    Free shipping
    $199.00
    8000Kicks - The Crossover Hemp Chelsea Boots For Men In Black, M14 | EU 48
    8000Kicks
    Free shipping
    $990.00
    Moncler Peak City Nubuck Chelsea Boots, Men, Brown, Size: 44
    Moncler
    $990.00
    Moncler Peak City Nubuck Chelsea Boots, Men, Brown, Size: 44
    Moncler
    $149.95
    Chaco Men's Fields Chelsea Waterproof Boot, Black, 10.5
    Amazon.com
    54
    Free shipping
    $149.95
    Chaco Men's Fields Chelsea Waterproof Boot, Black, 10.5
    Amazon.com
    54
    $150.00
    Men's Stonington Chelsea Boots, Leather Dark Oakwood 10.5 M(D), Leather/Rubber | L.L.Bean
    L.L.Bean
    In store
    50% Off*
    Free shipping
    $150.00
    Men's Stonington Chelsea Boots, Leather Dark Oakwood 10.5 M(D), Leather/Rubber | L.L.Bean
    L.L.Bean
    50% Off*
    $149.99
    Carhartt Men's Wedge 5-Inch Chelsea Pullon Soft Toe fw5033m Dark Bison Oil Tanned 10.5 Wide
    Amazon.com
    453
    Free shipping
    $149.99
    Carhartt Men's Wedge 5-Inch Chelsea Pullon Soft Toe fw5033m Dark Bison Oil Tanned 10.5 Wide
    Amazon.com
    453
    $99.99
    Redhead ASC IV Chelsea Insulated Waterproof Boots For Men - Brown - 9m
    Cabela's
    In store
    $99.99
    Redhead ASC IV Chelsea Insulated Waterproof Boots For Men - Brown - 9m
    Cabela's
    $99.76
    Sperry Mens Cold Bay Chelsea
    Amazon.com
    3
    Free shipping
    $99.76
    Sperry Mens Cold Bay Chelsea
    Amazon.com
    3
    $47.99
    $119.99
    Men's Terrain All Weather Chelsea Boots - Lands' End - Brown - 11
    Lands' End
    60% off
    $47.99
    $119.99
    Men's Terrain All Weather Chelsea Boots - Lands' End - Brown - 11
    Lands' End
    $129.99
    Timberland Redwood Falls Chelsea Boot | Men's | Black | Size 10.5 | Boots | Lug
    DSW
    87
    Free shipping
    $129.99
    Timberland Redwood Falls Chelsea Boot | Men's | Black | Size 10.5 | Boots | Lug
    DSW
    87
    $249.95
    Danner Men's Tramline Chelsea 917 GTX Waterproof Boots In Major Brown Size 10.5m
    WorkBoots.com
    $249.95
    Danner Men's Tramline Chelsea 917 GTX Waterproof Boots In Major Brown Size 10.5m
    WorkBoots.com
    $144.50
    $180.00
    Dr. Martens 2976 Leather Chelsea Boots Boots Black : UK 9 (US Men's 10 - US Women's 11) M
    Zappos
    51
    19% off
    $144.50
    $180.00
    Dr. Martens 2976 Leather Chelsea Boots Boots Black : UK 9 (US Men's 10 - US Women's 11) M
    Zappos
    51
    $249.95
    Danner Men's Tramline Chelsea 917 GTX Waterproof Boots In Roasted Pecan Size 10.5m
    WorkBoots.com
    $249.95
    Danner Men's Tramline Chelsea 917 GTX Waterproof Boots In Roasted Pecan Size 10.5m
    WorkBoots.com
    $129.99
    Carhartt Men's Frontier Water Resistant Chelsea | Dark Brown | 10 m
    Carhartt
    1
    $129.99
    Carhartt Men's Frontier Water Resistant Chelsea | Dark Brown | 10 m
    Carhartt
    1
    $99.99
    Redhead ASC IV Chelsea Insulated Waterproof Boots For Men - Brown - 11m
    Bass Pro Shops
    $99.99
    Redhead ASC IV Chelsea Insulated Waterproof Boots For Men - Brown - 11m
    Bass Pro Shops
    $249.95
    Danner Men's Tramline Chelsea 917 GTX Waterproof Boots In Major Brown Size 10.5m
    TacticalGear.com
    $249.95
    Danner Men's Tramline Chelsea 917 GTX Waterproof Boots In Major Brown Size 10.5m
    TacticalGear.com
    $139.99
    Timberland Redwood Edge Chelsea Boot | Men's | Brown | Size 10 | Boots
    DSW
    In store
    Free shipping
    $139.99
    Timberland Redwood Edge Chelsea Boot | Men's | Brown | Size 10 | Boots
    DSW
    Free shipping
    $139.96
    Frye & Co. Hank Chelsea Boot | Men's | Cognac | Size 9 | Boots
    DSW
    Free shipping
    $139.96
    Frye & Co. Hank Chelsea Boot | Men's | Cognac | Size 9 | Boots
    DSW
    Free shipping