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Chelsea Boots for Men

  • All Boots
  • Chelsea
  • Chukka
  • Combat & Lace-Up
  • Comfort
  • Dress Boots
  • Rain & Snow
  • Boots Under $100
104 items
New Tunley Chelsea Boot (Men)
BOSS

New Tunley Chelsea Boot (Men)

$89.97 – $149.97Current Price $89.97 to $149.97
(Up to 54% off)Up to 54% off.
$199.00Comparable value $199.00
(1)
Ludlow Chelsea Boot (Men)
New
John Varvatos

Ludlow Chelsea Boot (Men)

$399.97Current Price $399.97
(49% off)49% off.
$798.00Comparable value $798.00
Harley Chelsea Boot (Men)
AllSaints

Harley Chelsea Boot (Men)

$129.97Current Price $129.97
(56% off)56% off.
$299.00Comparable value $299.00
(24)
2976 Wintergrip Water Resistant Chelsea Boot (Men)
Dr. Martens

2976 Wintergrip Water Resistant Chelsea Boot (Men)

$99.97Current Price $99.97
(47% off)47% off.
$190.00Comparable value $190.00
(54)
Martin Chelsea Boot (Men)
VINTAGE FOUNDRY

Martin Chelsea Boot (Men)

$49.97Current Price $49.97
(71% off)71% off.
$175.00Comparable value $175.00
(7)
Norwich Chelsea Boot (Men)
Ted Baker London

Norwich Chelsea Boot (Men)

$89.97Current Price $89.97
(52% off)52% off.
$190.00Comparable value $190.00
Wren Chelsea Boot (Men)
Allen Edmonds

Wren Chelsea Boot (Men)

$159.97Current Price $159.97
(67% off)67% off.
$495.00Comparable value $495.00
(5)
Grand Atlantic Chelsea Boot (Men)
Cole Haan

Grand Atlantic Chelsea Boot (Men)

$44.97Current Price $44.97
(Extra 40% off)Includes extra 40% off.
$74.96Previous Price $74.96
$200.00Comparable value $200.00
Price Drop
(5)
Only a few left
Chamberlin Grand Water Resistant Chelsea Boot (Men)
Cole Haan

Chamberlin Grand Water Resistant Chelsea Boot (Men)

$58.48 – $119.97Current Price $58.48 to $119.97
(Extra 40% off select items)Includes extra 40% off select items.
$97.47Previous Price $97.47
$260.00Comparable value $260.00
Price Drop
(10)
Colby Chelsea Boot (Men)
BOSS

Colby Chelsea Boot (Men)

$149.97Current Price $149.97
(24% off)24% off.
$199.00Comparable value $199.00
(2)
Tyler Chelsea Boot (Men)
Frye

Tyler Chelsea Boot (Men)

$67.48 – $129.97Current Price $67.48 to $129.97
(Extra 40% off select items)Includes extra 40% off select items.
$112.47Previous Price $112.47
$258.00Comparable value $258.00
Price Drop
(34)
Only a few left
Sofa Hi Platform Chelsea Boot (Men)
New
McQueen

Sofa Hi Platform Chelsea Boot (Men)

$449.97Current Price $449.97
(67% off)67% off.
$1,390.00Comparable value $1,390.00
Only a few left
Driggs Chelsea Boot (Men)
Allen Edmonds

Driggs Chelsea Boot (Men)

$199.97Current Price $199.97
(59% off)59% off.
$495.00Comparable value $495.00
(2)
Crip Chelsea Boot (Men)
Roberto Cavalli

Crip Chelsea Boot (Men)

$159.97Current Price $159.97
(71% off)71% off.
$570.00Comparable value $570.00
(3)
Eddison Chelsea Boot (Men)
Magnanni

Eddison Chelsea Boot (Men)

$97.48 – $249.97Current Price $97.48 to $249.97
(Extra 40% off select items)Includes extra 40% off select items.
$162.48Previous Price $162.48
$465.00Comparable value $465.00
Price Drop
Dressel Chelsea Boot (Men)
TO BOOT NEW YORK

Dressel Chelsea Boot (Men)

$199.97 – $229.97Current Price $199.97 to $229.97
(Up to 57% off)Up to 57% off.
$475.00Comparable value $475.00
(1)
Colby Chelsea Boot (Men)
BOSS

Colby Chelsea Boot (Men)

$58.48Current Price $58.48
(Extra 40% off)Includes extra 40% off.
$97.48Previous Price $97.48
$199.00Comparable value $199.00
Price Drop
Borland Chelsea Boot (Men)
Johnston & Murphy

Borland Chelsea Boot (Men)

$33.57 – $79.97Current Price $33.57 to $79.97
(Extra 40% off select items)Includes extra 40% off select items.
$55.96Previous Price $55.96
$160.00Comparable value $160.00
Price Drop
(4)
Lockhart Mini Lug Suede Chelsea Boot (Men)
New
Nordstrom

Lockhart Mini Lug Suede Chelsea Boot (Men)

$49.97Current Price $49.97
(58% off)58% off.
$119.95Comparable value $119.95
(2)
Calev Chelsea Boot (Men)
BOSS

Calev Chelsea Boot (Men)

$149.97Current Price $149.97
(34% off)34% off.
$230.00Comparable value $230.00
Liverpool Chelsea Boot (Men)
Allen Edmonds

Liverpool Chelsea Boot (Men)

$199.97Current Price $199.97
(59% off)59% off.
$495.00Comparable value $495.00
(50)
Langton Chelsea Boot (Men)
ALDO

Langton Chelsea Boot (Men)

$74.97Current Price $74.97
(50% off)50% off.
$150.00Comparable value $150.00
Chalet Chelsea Boot (Men)
Florsheim

Chalet Chelsea Boot (Men)

$99.97Current Price $99.97
(31% off)31% off.
$145.00Comparable value $145.00
(120)
Creeper Chelsea Boot (Men)
New
Burberry

Creeper Chelsea Boot (Men)

$399.97Current Price $399.97
(68% off)68% off.
$1,250.00Comparable value $1,250.00
Only a few left
Enrico Chelsea Boot (Men)
Aquatalia

Enrico Chelsea Boot (Men)

$229.97Current Price $229.97
(58% off)58% off.
$550.00Comparable value $550.00
Trunk Chelsea Boot (Men)
McQueen

Trunk Chelsea Boot (Men)

$479.97Current Price $479.97
(65% off)65% off.
$1,390.00Comparable value $1,390.00
Only a few left
Norwich Chelsea Boot (Men)
Ted Baker

Norwich Chelsea Boot (Men)

$89.97Current Price $89.97
(52% off)52% off.
$190.00Comparable value $190.00
(1)
Fenton Lug Sole Chelsea Boot (Men)
Steve Madden

Fenton Lug Sole Chelsea Boot (Men)

$29.99 – $79.97Current Price $29.99 to $79.97
(Extra 40% off select items)Includes extra 40% off select items.
$49.99Previous Price $49.99
$130.00Comparable value $130.00
Price Drop
(6)
Truman Chelsea Boot (Men)
Dockers®

Truman Chelsea Boot (Men)

$59.97Current Price $59.97
(36% off)36% off.
$95.00Comparable value $95.00
(5)
Chelsea Boot (Men)
Santoni

Chelsea Boot (Men)

$739.97Current Price $739.97
(52% off)52% off.
$1,570.00Comparable value $1,570.00
Only a few left
Peter Chelsea Boot (Men)
VITTORIO RUSSO

Peter Chelsea Boot (Men)

$54.57 – $129.97Current Price $54.57 to $129.97
(Extra 40% off select items)Includes extra 40% off select items.
$90.96Previous Price $90.96
$225.00Comparable value $225.00
Price Drop
(6)
Only a few left
Neumel Chelsea Boot (Men)
UGG®

Neumel Chelsea Boot (Men)

$89.97Current Price $89.97
(35% off)35% off.
$140.00Comparable value $140.00
(29)
Shepton Easy Chelsea Boot (Men)
Clarks®

Shepton Easy Chelsea Boot (Men)

$94.97Current Price $94.97
(26% off)26% off.
$130.00Comparable value $130.00
Hybrid Low Boy Chelsea Boot (Men)
Ariat

Hybrid Low Boy Chelsea Boot (Men)

$99.97Current Price $99.97
(37% off)37% off.
$159.95Comparable value $159.95
(27)
Maximo Chelsea Boot (Men)
Bruno Magli

Maximo Chelsea Boot (Men)

$199.97Current Price $199.97
(55% off)55% off.
$450.00Comparable value $450.00
Only a few left
Camo Jacquard Chelsea Boot (Men)
KARL LAGERFELD PARIS

Camo Jacquard Chelsea Boot (Men)

$119.97Current Price $119.97
(40% off)40% off.
$200.00Comparable value $200.00
Gainsly Chelsea Boot (Men)
New
Tommy Hilfiger

Gainsly Chelsea Boot (Men)

$59.97Current Price $59.97
(52% off)52% off.
$125.00Comparable value $125.00
(1)
Lyle Chelsea Boot (Men)
VINTAGE FOUNDRY

Lyle Chelsea Boot (Men)

$41.98 – $44.97Current Price $41.98 to $44.97
(Extra 40% off)Includes extra 40% off.
$69.98 – $74.96Previous Price $69.98 to $74.96
$200.00Comparable value $200.00
Price Drop
(3)
Adwin Chelsea Boot (Men)
Stuart Weitzman

Adwin Chelsea Boot (Men)

$194.98Current Price $194.98
(Extra 40% off)Includes extra 40% off.
$324.98Previous Price $324.98
$975.00Comparable value $975.00
Price Drop
(4)
Dylan Chelsea Boot (Men)
Frye

Dylan Chelsea Boot (Men)

$189.97Current Price $189.97
(52% off)52% off.
$398.00Comparable value $398.00
(14)
Only a few left
Karnak Plain Toe Chelsea Boot (Men)
NUNN BUSH

Karnak Plain Toe Chelsea Boot (Men)

$89.97Current Price $89.97
(25% off)25% off.
$120.00Comparable value $120.00
Attleboro Chelsea Boot (Men)
Timberland

Attleboro Chelsea Boot (Men)

$29.99Current Price $29.99
(Extra 40% off)Includes extra 40% off.
$49.99Previous Price $49.99
$130.00 – $140.00Comparable value $130.00 to $140.00
Price Drop
(9)
Sawyer Chelsea Boot (Men)
MADDEN

Sawyer Chelsea Boot (Men)

$20.97 – $49.97Current Price $20.97 to $49.97
(Extra 40% off select items)Includes extra 40% off select items.
$34.96Previous Price $34.96
$90.00Comparable value $90.00
Price Drop
(12)
Gabriel Creeper Chelsea Boot (Men)
Burberry

Gabriel Creeper Chelsea Boot (Men)

$429.97Current Price $429.97
(62% off)62% off.
$1,150.00Comparable value $1,150.00
(3)
Only a few left
Remington Chelsea Boot (Men)
Ted Baker London

Remington Chelsea Boot (Men)

$119.97Current Price $119.97
(45% off)45% off.
$220.00Comparable value $220.00
(2)
Shaw Suede Chelsea Boot (Men)
New
Magnanni

Shaw Suede Chelsea Boot (Men)

$239.97Current Price $239.97
(51% off)51% off.
$495.00Comparable value $495.00
Nello Chelsea Boot (Men)
Bruno Magli

Nello Chelsea Boot (Men)

$199.97Current Price $199.97
(49% off)49% off.
$395.00Comparable value $395.00
Loreno Chelsea Boot (Men)
FERRAGAMO

Loreno Chelsea Boot (Men)

$659.97Current Price $659.97
(48% off)48% off.
$1,290.00Comparable value $1,290.00
Jenson Chelsea Boot (Men)
Johnston & Murphy

Jenson Chelsea Boot (Men)

$81.88Current Price $81.88
(Extra 40% off)Includes extra 40% off.
$136.48Previous Price $136.48
$328.00Comparable value $328.00
Price Drop
(4)
Only a few left
Rafael Chelsea Boot (Men)
Bruno Magli

Rafael Chelsea Boot (Men)

$189.97Current Price $189.97
(57% off)57% off.
$450.00Comparable value $450.00
(1)
Storm Chelsea Rain Boot (Men)
Barbour

Storm Chelsea Rain Boot (Men)

$69.97Current Price $69.97
(51% off)51% off.
$145.00Comparable value $145.00
(2)
Wynford Chelsea Boot (Men)
ALDO

Wynford Chelsea Boot (Men)

$74.97Current Price $74.97
(50% off)50% off.
$150.00Comparable value $150.00
Charleston Chelsea Boot (Men)
TO BOOT NEW YORK

Charleston Chelsea Boot (Men)

$199.97 – $219.97Current Price $199.97 to $219.97
(Up to 52% off)Up to 52% off.
$425.00Comparable value $425.00
(6)
Otto Lug Chelsea Boot (Men)
Abound

Otto Lug Chelsea Boot (Men)

$49.97Current Price $49.97
(44% off)44% off.
$89.95Comparable value $89.95
(13)
Only a few left
x John Deere Segment 2.0 Waterproof Chelsea Boot (Men)
SKECHERS

x John Deere Segment 2.0 Waterproof Chelsea Boot (Men)

$59.97Current Price $59.97
(53% off)53% off.
$128.00Comparable value $128.00
(1)
Azzano Plain Toe Chelsea Boot (Men)
Florsheim

Azzano Plain Toe Chelsea Boot (Men)

$49.48Current Price $49.48
(Extra 40% off)Includes extra 40% off.
$82.47Previous Price $82.47
$145.00Comparable value $145.00
Price Drop
Rilyn Chelsea Boot (Men)
Steve Madden

Rilyn Chelsea Boot (Men)

$79.97Current Price $79.97
(50% off)50% off.
$160.00Comparable value $160.00
(16)
Upton Chelsea Boot (Men)
Johnston & Murphy

Upton Chelsea Boot (Men)

$129.97Current Price $129.97
(27% off)27% off.
$179.00Comparable value $179.00
(7)
Croc Embossed Leather Chelsea Boot (Men)
Donald Pliner

Croc Embossed Leather Chelsea Boot (Men)

$139.97Current Price $139.97
(57% off)57% off.
$328.00Comparable value $328.00
(5)
Wilder Chelsea Boot (Men)
Abound

Wilder Chelsea Boot (Men)

$49.97Current Price $49.97
(37% off)37% off.
$79.95Comparable value $79.95
(6)
Chelsea Boot (Men)
Rush by Gordon Rush

Chelsea Boot (Men)

$49.97Current Price $49.97
(60% off)60% off.
$125.00Comparable value $125.00
(36)
Roklan Chelsea Boot (Men)
Tommy Hilfiger

Roklan Chelsea Boot (Men)

$59.97Current Price $59.97
(53% off)53% off.
$129.00Comparable value $129.00
Wexford Chelsea Boot (Men)
New
Ariat

Wexford Chelsea Boot (Men)

$99.97Current Price $99.97
(47% off)47% off.
$189.95Comparable value $189.95
(4)
Only a few left
Kam Chelsea Boot (Men)
Magnanni

Kam Chelsea Boot (Men)

$279.97Current Price $279.97
(43% off)43% off.
$495.00Comparable value $495.00
(2)
Sesame Chelsea Boot (Men)
Tommy Hilfiger

Sesame Chelsea Boot (Men)

$54.97Current Price $54.97
(53% off)53% off.
$119.00Comparable value $119.00
(35)
Amos Chelsea Boot (Men)
New
Stuart Weitzman

Amos Chelsea Boot (Men)

$309.97Current Price $309.97
(47% off)47% off.
$595.00Comparable value $595.00
Clifton Waterproof Chelsea Duck Boot (Men)
Sperry

Clifton Waterproof Chelsea Duck Boot (Men)

$49.97Current Price $49.97
(54% off)54% off.
$110.00Comparable value $110.00
(1)
Only a few left
George 2 Chelsea Boot (Men)
FERRAGAMO

George 2 Chelsea Boot (Men)

$529.97Current Price $529.97
(57% off)57% off.
$1,250.00Comparable value $1,250.00
Studded Chelsea Boot (Men)
KARL LAGERFELD PARIS

Studded Chelsea Boot (Men)

$89.97Current Price $89.97
(81% off)81% off.
$495.00Comparable value $495.00
(4)
Bonn Leather Chelsea Boot (Men)
Magnanni

Bonn Leather Chelsea Boot (Men)

$279.97Current Price $279.97
(43% off)43% off.
$495.00Comparable value $495.00
(8)
Connor Suede Chelsea Boot (Men)
Frye

Connor Suede Chelsea Boot (Men)

$99.97Current Price $99.97
(49% off)49% off.
$198.00Comparable value $198.00
Darwin Plain Toe Chelsea Boot (Men)
VINTAGE FOUNDRY

Darwin Plain Toe Chelsea Boot (Men)

$109.97Current Price $109.97
(50% off)50% off.
$220.00Comparable value $220.00
(4)
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