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Chelsea Boots for Men

  • All Boots
  • Chelsea
  • Chukka
  • Combat & Lace-Up
  • Comfort
  • Dress Boots
  • Rain & Snow
  • Boots Under $100
135 items
Sawyer Chelsea Boot (Men)
New Markdown
Steve Madden

Sawyer Chelsea Boot (Men)

$34.96 – $49.97Current Price $34.96 to $49.97
(Up to 61% off select items)Up to 61% off select items.
$90.00Comparable value $90.00
(10)
Bowery Chelsea Boot (Men)
New Markdown
Frye

Bowery Chelsea Boot (Men)

$125.96 – $179.97Current Price $125.96 to $179.97
(Up to 61% off select items)Up to 61% off select items.
$328.00Comparable value $328.00
(26)
Wren Chelsea Boot (Men)
Allen Edmonds

Wren Chelsea Boot (Men)

$159.97Current Price $159.97
(67% off)67% off.
$495.00Comparable value $495.00
(4)
Chalet Chelsea Boot (Men)
New!
Florsheim

Chalet Chelsea Boot (Men)

$99.97Current Price $99.97
(31% off)31% off.
$145.00Comparable value $145.00
(114)
Nash Chelsea Boot (Men)
New!
Abound

Nash Chelsea Boot (Men)

$59.97Current Price $59.97
(33% off)33% off.
$89.95Comparable value $89.95
Chamberlin Grand Water Resistant Chelsea Boot (Men)
Cole Haan

Chamberlin Grand Water Resistant Chelsea Boot (Men)

$129.97Current Price $129.97
(50% off)50% off.
$260.00Comparable value $260.00
(8)
Grand Atlantic Chelsea Boot (Men)
New Markdown
Cole Haan

Grand Atlantic Chelsea Boot (Men)

$74.96 – $99.97Current Price $74.96 to $99.97
(Up to 62% off select items)Up to 62% off select items.
$200.00Comparable value $200.00
(3)
Borland Chelsea Boot (Men)
New Markdown
Johnston & Murphy

Borland Chelsea Boot (Men)

$55.96 – $79.97Current Price $55.96 to $79.97
(Up to 65% off select items)Up to 65% off select items.
$160.00Comparable value $160.00
(1)
Lyle Chelsea Boot (Men)
New Markdown
VINTAGE FOUNDRY

Lyle Chelsea Boot (Men)

$69.98 – $74.96Current Price $69.98 to $74.96
(Up to 65% off)Up to 65% off.
$200.00Comparable value $200.00
(2)
Dylan Chelsea Boot (Men)
Dockers®

Dylan Chelsea Boot (Men)

$59.97Current Price $59.97
(36% off)36% off.
$95.00Comparable value $95.00
(5)
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
Chamberlin Grand Chelsea Boot (Men)
New Markdown
Cole Haan

Chamberlin Grand Chelsea Boot (Men)

$97.47Current Price $97.47
(62% off)62% off.
$260.00Comparable value $260.00
(1)
Attleboro Chelsea Boot (Men)
New Markdown
Timberland

Attleboro Chelsea Boot (Men)

$49.99 – $69.97Current Price $49.99 to $69.97
(Up to 61% off select items)Up to 61% off select items.
$130.00 – $140.00Comparable value $130.00 to $140.00
(7)
Jaxen Easy Chelsea Boot (Men)
New!
Clarks®

Jaxen Easy Chelsea Boot (Men)

$99.97Current Price $99.97
(16% off)16% off.
$120.00Comparable value $120.00
Hudson Yards 2.0 Pull-On Boot (Men)
New Markdown
Marc Joseph New York

Hudson Yards 2.0 Pull-On Boot (Men)

$55.96 – $59.96Current Price $55.96 to $59.96
(Up to 71% off)Up to 71% off.
$195.00Comparable value $195.00
(2)
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)
Herman Water Resistant Chelsea Boot (Men)
New Markdown
Eastland

Herman Water Resistant Chelsea Boot (Men)

$59.96 – $79.97Current Price $59.96 to $79.97
(Up to 55% off select items)Up to 55% off select items.
$135.00Comparable value $135.00
(2)
Newmark Grand Water Resistant Chelsea Boot (Men)
Cole Haan

Newmark Grand Water Resistant Chelsea Boot (Men)

$129.97Current Price $129.97
(63% off)63% off.
$360.00Comparable value $360.00
(7)
Peter Chelsea Boot (Men)
New Markdown
VITTORIO RUSSO

Peter Chelsea Boot (Men)

$84.48 – $129.97Current Price $84.48 to $129.97
(Up to 62% off select items)Up to 62% off select items.
$225.00Comparable value $225.00
(3)
Emden Lug Sole Chelsea Boot (Men)
New Markdown
Steve Madden

Emden Lug Sole Chelsea Boot (Men)

$55.96Current Price $55.96
(60% off)60% off.
$140.00Comparable value $140.00
Dante Chelsea Boot (Men)
New!
GREATS

Dante Chelsea Boot (Men)

$69.97Current Price $69.97
(72% off)72% off.
$250.00Comparable value $250.00
Only a few left
Wynford Chelsea Boot (Men)
New!
ALDO

Wynford Chelsea Boot (Men)

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

Estiban Chelsea Boot (Men)

$54.97Current Price $54.97
(35% off)35% off.
$85.00Comparable value $85.00
(5)
Forge Chelsea Boot (Men)
New Markdown
Florsheim

Forge Chelsea Boot (Men)

$71.48 – $82.47Current Price $71.48 to $82.47
(Up to 45% off)Up to 45% off.
$130.00Comparable value $130.00
(1)
Roklan Chelsea Boot (Men)
Tommy Hilfiger

Roklan Chelsea Boot (Men)

$59.97Current Price $59.97
(53% off)53% off.
$129.00Comparable value $129.00
Langton Chelsea Boot (Men)
New!
ALDO

Langton Chelsea Boot (Men)

$74.97Current Price $74.97
(50% off)50% off.
$150.00Comparable value $150.00
Slabtown 62 Waterproof Chelsea Boot (Men)
New Markdown
SOREL

Slabtown 62 Waterproof Chelsea Boot (Men)

$74.96Current Price $74.96
(55% off)55% off.
$170.00Comparable value $170.00
(1)
Only a few left
Ruvo Chelsea Boot (Men)
New Markdown
Florsheim

Ruvo Chelsea Boot (Men)

$82.47Current Price $82.47
(45% off)45% off.
$150.00Comparable value $150.00
(22)
Dakoda Chelsea Boot (Men)
New Markdown
NUNN BUSH

Dakoda Chelsea Boot (Men)

$31.47Current Price $31.47
(66% off)66% off.
$95.00Comparable value $95.00
(25)
Only a few left
Jenson Chelsea Boot (Men)
New Markdown
Johnston & Murphy

Jenson Chelsea Boot (Men)

$136.48Current Price $136.48
(58% off)58% off.
$328.00Comparable value $328.00
(3)
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
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
(48)
Bonn Leather Chelsea Boot (Men)
New Markdown
Magnanni

Bonn Leather Chelsea Boot (Men)

$195.96 – $279.97Current Price $195.96 to $279.97
(Up to 60% off select items)Up to 60% off select items.
$495.00Comparable value $495.00
(7)
Roswel Plain Toe Chelsea Boot (Men)
New Markdown
Steve Madden

Roswel Plain Toe Chelsea Boot (Men)

$67.47Current Price $67.47
(51% off)51% off.
$140.00Comparable value $140.00
Carden Chelsea Boot (Men)
New Markdown
Dune London

Carden Chelsea Boot (Men)

$62.96Current Price $62.96
(65% off)65% off.
$180.00Comparable value $180.00
Only a few left
Cryus Chelsea Boot (Men)
New Markdown
Eastland

Cryus Chelsea Boot (Men)

$44.96 – $44.97Current Price $44.96 to $44.97
(50% off)50% off.
$90.00Comparable value $90.00
(11)
Osmond Chelsea Boot (Men)
New Markdown
VANCE CO

Osmond Chelsea Boot (Men)

$59.96 – $79.97Current Price $59.96 to $79.97
(Up to 45% off select items)Up to 45% off select items.
$109.99Comparable value $109.99
(1)
Slater Chelsea Boot (Men)
New Markdown
VANCE CO

Slater Chelsea Boot (Men)

$44.98 – $56.22Current Price $44.98 to $56.22
(Up to 59% off)Up to 59% off.
$109.99Comparable value $109.99
(1)
Only a few left
Wilder Chelsea Boot (Men)
Abound

Wilder Chelsea Boot (Men)

$49.97Current Price $49.97
(37% off)37% off.
$79.95Comparable value $79.95
(6)
Fenton Lug Sole Chelsea Boot (Men)
New!
Steve Madden

Fenton Lug Sole Chelsea Boot (Men)

$79.97Current Price $79.97
(38% off)38% off.
$130.00Comparable value $130.00
(4)
Memille Chelsea Boot (Men)
New Markdown
Steve Madden

Memille Chelsea Boot (Men)

$34.99Current Price $34.99
(58% off)58% off.
$85.00Comparable value $85.00
Bonham Water Repellent Chelsea Boot (Men)
New Markdown
Vince

Bonham Water Repellent Chelsea Boot (Men)

$99.99Current Price $99.99
(71% off)71% off.
$350.00Comparable value $350.00
(1)
Brody Chelsea Boot (Men)
Johnston & Murphy

Brody Chelsea Boot (Men)

$69.97Current Price $69.97
(57% off)57% off.
$165.00Comparable value $165.00
(18)
Creed Chelsea Boot (Men)
AllSaints

Creed Chelsea Boot (Men)

$139.97Current Price $139.97
(53% off)53% off.
$299.00Comparable value $299.00
(2)
Only a few left
Clifton Waterproof Chelsea Duck Boot (Men)
New!
Sperry

Clifton Waterproof Chelsea Duck Boot (Men)

$49.97Current Price $49.97
(54% off)54% off.
$110.00Comparable value $110.00
Only a few left
Chimney Pond Chelsea Boot (Men)
New Markdown
Eastland

Chimney Pond Chelsea Boot (Men)

$69.96 – $74.96Current Price $69.96 to $74.96
(Up to 51% off)Up to 51% off.
$145.00Comparable value $145.00
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)
Tyler Chelsea Boot (Men)
Frye

Tyler Chelsea Boot (Men)

$149.97Current Price $149.97
(41% off)41% off.
$258.00Comparable value $258.00
(34)
Newmark Grand Chelsea Boot (Men)
New Markdown
Cole Haan

Newmark Grand Chelsea Boot (Men)

$97.47Current Price $97.47
(72% off)72% off.
$360.00Comparable value $360.00
Sesame Chelsea Boot (Men)
Tommy Hilfiger

Sesame Chelsea Boot (Men)

$54.97Current Price $54.97
(53% off)53% off.
$119.00Comparable value $119.00
(32)
Townsend Chelsea Boot (Men)
New Markdown
Dockers®

Townsend Chelsea Boot (Men)

$29.96Current Price $29.96
(68% off)68% off.
$95.00Comparable value $95.00
(1)
'Daily Double' Chelsea Boot (Men)
New Markdown
Eastland

'Daily Double' Chelsea Boot (Men)

$74.96Current Price $74.96
(40% off)40% off.
$125.00Comparable value $125.00
(8)
Burlo Leather Chelsea Boot (Men)
New Markdown
Magnanni

Burlo Leather Chelsea Boot (Men)

$137.48 – $249.97Current Price $137.48 to $249.97
(Up to 69% off select items)Up to 69% off select items.
$450.00Comparable value $450.00
(32)
Dylan Chelsea Boot (Men)
Frye

Dylan Chelsea Boot (Men)

$189.97Current Price $189.97
(52% off)52% off.
$398.00Comparable value $398.00
(13)
Only a few left
Delton Plain Toe Chelsea Boot (Men)
NUNN BUSH

Delton Plain Toe Chelsea Boot (Men)

$54.97Current Price $54.97
(42% off)42% off.
$95.00Comparable value $95.00
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)
Lewis Chelsea Boot (Men)
New Markdown
Johnston & Murphy

Lewis Chelsea Boot (Men)

$49.99Current Price $49.99
(61% off)61% off.
$129.00Comparable value $129.00
(5)
Norwich Chelsea Boot (Men)
New!
Ted Baker

Norwich Chelsea Boot (Men)

$89.97Current Price $89.97
(52% off)52% off.
$190.00Comparable value $190.00
Harley Chelsea Boot (Men)
AllSaints

Harley Chelsea Boot (Men)

$129.97Current Price $129.97
(56% off)56% off.
$299.00Comparable value $299.00
(24)
Berton Chelsea Boot (Men)
Tommy Hilfiger

Berton Chelsea Boot (Men)

$59.97Current Price $59.97
(49% off)49% off.
$119.00Comparable value $119.00
Rilyn Chelsea Boot (Men)
Steve Madden

Rilyn Chelsea Boot (Men)

$79.97Current Price $79.97
(50% off)50% off.
$160.00Comparable value $160.00
(13)
Hardie II Chelsea Boot (Men)
Dr. Martens

Hardie II Chelsea Boot (Men)

$99.97Current Price $99.97
(16% off)16% off.
$120.00Comparable value $120.00
(58)
Parker Chelsea Boot (Men)
NEW YORK AND COMPANY

Parker Chelsea Boot (Men)

$39.97Current Price $39.97
(50% off)50% off.
$80.00Comparable value $80.00
(6)
Only a few left
Dressel Chelsea Boot (Men)
New Markdown
TO BOOT NEW YORK

Dressel Chelsea Boot (Men)

$149.96 – $199.97Current Price $149.96 to $199.97
(Up to 68% off select items)Up to 68% off select items.
$475.00Comparable value $475.00
(1)
Grand Chelsea Boot (Men)
Cole Haan

Grand Chelsea Boot (Men)

$54.98Current Price $54.98
(63% off)63% off.
$150.00Comparable value $150.00
Wesley Chelsea Boot (Men)
New Markdown
Steve Madden

Wesley Chelsea Boot (Men)

$55.23 – $63.72Current Price $55.23 to $63.72
(Up to 63% off)Up to 63% off.
$150.00Comparable value $150.00
(1)
Otis II Chelsea Boot (Men)
NUNN BUSH

Otis II Chelsea Boot (Men)

$89.97Current Price $89.97
(18% off)18% off.
$110.00Comparable value $110.00
(1)
Azzano Plain Toe Chelsea Boot (Men)
New Markdown
Florsheim

Azzano Plain Toe Chelsea Boot (Men)

$82.47Current Price $82.47
(43% off)43% off.
$145.00Comparable value $145.00
Colby Chelsea Boot (Men)
BOSS

Colby Chelsea Boot (Men)

$149.97Current Price $149.97
(24% off)24% off.
$199.00Comparable value $199.00
(2)
Truman Chelsea Boot (Men)
Dockers®

Truman Chelsea Boot (Men)

$59.97Current Price $59.97
(36% off)36% off.
$95.00Comparable value $95.00
(2)
Huston Chelsea Boot (Men)
Roberto Cavalli

Huston Chelsea Boot (Men)

$159.97Current Price $159.97
(70% off)70% off.
$545.00Comparable value $545.00
(3)
Colby Chelsea Boot (Men)
New Markdown
BOSS

Colby Chelsea Boot (Men)

$97.48 – $149.97Current Price $97.48 to $149.97
(Up to 51% off select items)Up to 51% off select items.
$199.00Comparable value $199.00
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