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Comfort Boots for Men

  • All Comfort
  • Boots
  • Dress Shoes
  • Loafers & Oxfords
  • Sneakers
181 items
Theo Chukka Boot (Men)
Børn

Theo Chukka Boot (Men)

$59.97 – $79.97Current Price $59.97 to $79.97
(Up to 53% off select items)Up to 53% off select items.
$130.00Comparable value $130.00
(6)
2.Zerogrand Chukka Boot (Men)
Cole Haan

2.Zerogrand Chukka Boot (Men)

$99.97Current Price $99.97
(70% off)70% off.
$338.00Comparable value $338.00
(395)
Chase Plain Toe Chukka Boot - Wide Width Available (Men)
NUNN BUSH

Chase Plain Toe Chukka Boot - Wide Width Available (Men)

$44.97 – $54.97Current Price $44.97 to $54.97
(Up to 52% off)Up to 52% off.
$90.00 – $95.00Comparable value $90.00 to $95.00
(12)
Boswell Chukka Boot (Men)
Johnston & Murphy

Boswell Chukka Boot (Men)

$89.97Current Price $89.97
(48% off)48% off.
$175.00Comparable value $175.00
(10)
Upton Chukka Boot (Men)
New!
Johnston & Murphy

Upton Chukka Boot (Men)

$69.97Current Price $69.97
(58% off)58% off.
$169.00Comparable value $169.00
(18)
Shepton Chukka Boot (Men)
Clarks®

Shepton Chukka Boot (Men)

$74.97Current Price $74.97
(Up to 31% off)Up to 31% off.
$100.00 – $110.00Comparable value $100.00 to $110.00
(1)
Calder Chukka Boot (Men)
Johnston & Murphy

Calder Chukka Boot (Men)

$79.97Current Price $79.97
(51% off)51% off.
$165.00Comparable value $165.00
(21)
Borland Chelsea Boot (Men)
New!
Johnston & Murphy

Borland Chelsea Boot (Men)

$79.97Current Price $79.97
(50% off)50% off.
$160.00Comparable value $160.00
Weltridge Side Zip Boot (Men)
Clarks®

Weltridge Side Zip Boot (Men)

$94.97Current Price $94.97
(26% off)26% off.
$130.00Comparable value $130.00
(1)
Grand Chelsea Boot (Men)
Clear The Rack
Cole Haan

Grand Chelsea Boot (Men)

$41.23Current Price $41.23
(Extra 25% off)Includes extra 25% off.
$54.98Previous Price $54.98
$150.00Comparable value $150.00
Lincoln Chukka (Men)
Børn

Lincoln Chukka (Men)

$89.97Current Price $89.97
(41% off)41% off.
$155.00Comparable value $155.00
(4)
Morse GRANDFØAM Chukka Boot (Men)
New!
Cole Haan

Morse GRANDFØAM Chukka Boot (Men)

$129.97Current Price $129.97
(40% off)40% off.
$220.00Comparable value $220.00
Dee Chukka Boot (Men)
Dockers®

Dee Chukka Boot (Men)

$39.97Current Price $39.97
(57% off)57% off.
$95.00Comparable value $95.00
Chamberlin Grand Chukka Boot (Men)
Cole Haan

Chamberlin Grand Chukka Boot (Men)

$97.47 – $129.97Current Price $97.47 to $129.97
(Up to 66% off select items)Up to 66% off select items.
$290.00Comparable value $290.00
(1)
Chalet Chelsea Boot (Men)
Florsheim

Chalet Chelsea Boot (Men)

$99.97Current Price $99.97
(31% off)31% off.
$145.00Comparable value $145.00
(111)
Azzano Plain Toe Chukka Boot (Men)
Florsheim

Azzano Plain Toe Chukka Boot (Men)

$109.97Current Price $109.97
(24% off)24% off.
$145.00Comparable value $145.00
Grand Remix Chukka Boot (Men)
Cole Haan

Grand Remix Chukka Boot (Men)

$99.97Current Price $99.97
(Up to 56% off)Up to 56% off.
$220.00 – $230.00Comparable value $220.00 to $230.00
(14)
Chalet Leather Cap Toe Boot (Men)
Florsheim

Chalet Leather Cap Toe Boot (Men)

$109.97Current Price $109.97
(29% off)29% off.
$155.00Comparable value $155.00
(16)
Thomson Chukka Boot (Men)
Børn

Thomson Chukka Boot (Men)

$89.97Current Price $89.97
(30% off)30% off.
$130.00Comparable value $130.00
(25)
Grand Atlantic Chukka Boot - Wide Width Available (Men)
Cole Haan

Grand Atlantic Chukka Boot - Wide Width Available (Men)

$74.97 – $99.97Current Price $74.97 to $99.97
(Up to 62% off select items)Up to 62% off select items.
$200.00Comparable value $200.00
(38)
Eli Suede Chukka Boot (Men)
Børn

Eli Suede Chukka Boot (Men)

$89.97Current Price $89.97
(30% off)30% off.
$130.00Comparable value $130.00
(1)
Hugo Boot
Eastland

Hugo Boot

$44.97 – $59.97Current Price $44.97 to $59.97
(Up to 55% off select items)Up to 55% off select items.
$100.00Comparable value $100.00
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
(5)
Maplewalk Moc Toe Boot (Men)
Clarks®

Maplewalk Moc Toe Boot (Men)

$79.97Current Price $79.97
(33% off)33% off.
$120.00Comparable value $120.00
(6)
Attleboro Chelsea Boot (Men)
New!
Timberland

Attleboro Chelsea Boot (Men)

$69.97Current Price $69.97
(Up to 50% off)Up to 50% off.
$130.00 – $140.00Comparable value $130.00 to $140.00
(6)
Steadwell Plain Toe Chukka Boot (Men)
Clarks®

Steadwell Plain Toe Chukka Boot (Men)

$79.97Current Price $79.97
(27% off)27% off.
$110.00Comparable value $110.00
High Fidelity Leather Boot (Men)
Eastland

High Fidelity Leather Boot (Men)

$79.97 – $119.97Current Price $79.97 to $119.97
(Up to 40% off)Up to 40% off.
$135.00Comparable value $135.00
(1)
Esmond Chukka Boot (Men)
Dockers®

Esmond Chukka Boot (Men)

$59.97Current Price $59.97
(36% off)36% off.
$95.00Comparable value $95.00
Grand Atlantic Chelsea Boot (Men)
Cole Haan

Grand Atlantic Chelsea Boot (Men)

$74.97 – $99.97Current Price $74.97 to $99.97
(Up to 62% off select items)Up to 62% off select items.
$200.00Comparable value $200.00
(2)
TOP-SIDER Newman Water Resistant Chukka Boot (Men)
Sperry

TOP-SIDER Newman Water Resistant Chukka Boot (Men)

$39.97Current Price $39.97
(60% off)60% off.
$100.00Comparable value $100.00
(2)
Only a few left
Truman Chelsea Boot (Men)
Dockers®

Truman Chelsea Boot (Men)

$59.97Current Price $59.97
(36% off)36% off.
$95.00Comparable value $95.00
(1)
Payton Mini Lug Pebbled Leather Chukka Boot (Men)
Nordstrom

Payton Mini Lug Pebbled Leather Chukka Boot (Men)

$69.97Current Price $69.97
(46% off)46% off.
$129.95Comparable value $129.95
(12)
Only a few left
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
(6)
Seth Memory Foam Chukka Boot (Men)
Eastland

Seth Memory Foam Chukka Boot (Men)

$44.97Current Price $44.97
(50% off)50% off.
$90.00Comparable value $90.00
(1)
Jack Chukka Boot (Men)
Eastland

Jack Chukka Boot (Men)

$89.97Current Price $89.97
(28% off)28% off.
$125.00Comparable value $125.00
(1)
Ozark II Chukka Boot (Men)
NUNN BUSH

Ozark II Chukka Boot (Men)

$89.97Current Price $89.97
(18% off)18% off.
$110.00Comparable value $110.00
(3)
Ruvo Chelsea Boot (Men)
Florsheim

Ruvo Chelsea Boot (Men)

$109.97Current Price $109.97
(26% off)26% off.
$150.00Comparable value $150.00
(21)
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
Seth Chukka Boot (Men)
Børn

Seth Chukka Boot (Men)

$89.97Current Price $89.97
(35% off)35% off.
$140.00Comparable value $140.00
(7)
Circuit Plain Toe Chukka Boot - Wide Width Available (Men)
NUNN BUSH

Circuit Plain Toe Chukka Boot - Wide Width Available (Men)

$54.97Current Price $54.97
(38% off)38% off.
$90.00Comparable value $90.00
(17)
Esmond Plain Toe Chukka Boot (Men)
Dockers®

Esmond Plain Toe Chukka Boot (Men)

$69.97Current Price $69.97
(17% off)17% off.
$85.00Comparable value $85.00
(5)
Otto Chukka Boot - Wide Width Available (Men)
NUNN BUSH

Otto Chukka Boot - Wide Width Available (Men)

$44.97 – $79.97Current Price $44.97 to $79.97
(Up to 52% off)Up to 52% off.
$95.00 – $110.00Comparable value $95.00 to $110.00
(13)
Forge Chelsea Boot (Men)
Florsheim

Forge Chelsea Boot (Men)

$109.97Current Price $109.97
(15% off)15% off.
$130.00Comparable value $130.00
(1)
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
Cryus Chelsea Boot (Men)
Eastland

Cryus Chelsea Boot (Men)

$44.97 – $59.97Current Price $44.97 to $59.97
(Up to 50% off select items)Up to 50% off select items.
$90.00Comparable value $90.00
(11)
Biltmore Waterproof Chelsea Boot (Men)
UGG®

Biltmore Waterproof Chelsea Boot (Men)

$109.97Current Price $109.97
(26% off)26% off.
$150.00Comparable value $150.00
(54)
Only a few left
Townsend Chelsea Boot (Men)
Dockers®

Townsend Chelsea Boot (Men)

$39.97Current Price $39.97
(57% off)57% off.
$95.00Comparable value $95.00
(1)
Davis Lace-Up Boot (Men)
Dockers®

Davis Lace-Up Boot (Men)

$59.97Current Price $59.97
(36% off)36% off.
$95.00Comparable value $95.00
(6)
Delton Plain Toe Chukka Boot (Men)
NUNN BUSH

Delton Plain Toe Chukka Boot (Men)

$54.97Current Price $54.97
(42% off)42% off.
$95.00Comparable value $95.00
Dakoda Chelsea Boot (Men)
NUNN BUSH

Dakoda Chelsea Boot (Men)

$44.97 – $54.97Current Price $44.97 to $54.97
(Up to 52% off)Up to 52% off.
$95.00Comparable value $95.00
(25)
Wallaston Chukka Boot (Men)
Clarks®

Wallaston Chukka Boot (Men)

$79.97Current Price $79.97
(33% off)33% off.
$120.00Comparable value $120.00
(1)
Grand Lug Sole Boot (Men)
Cole Haan

Grand Lug Sole Boot (Men)

$99.97Current Price $99.97
(25% off)25% off.
$135.00Comparable value $135.00
(2)
Barrett Water Resistant Boot (Men)
Johnston & Murphy

Barrett Water Resistant Boot (Men)

$99.97Current Price $99.97
(45% off)45% off.
$185.00Comparable value $185.00
(60)
Moc Toe Boot (Men)
Dockers®

Moc Toe Boot (Men)

$64.97Current Price $64.97
(31% off)31% off.
$95.00Comparable value $95.00
(1)
Odell II Wingtip Boot (Men)
NUNN BUSH

Odell II Wingtip Boot (Men)

$89.97Current Price $89.97
(18% off)18% off.
$110.00Comparable value $110.00
(2)
Patterson Cap Toe Chukka Boot (Men)
Eastland

Patterson Cap Toe Chukka Boot (Men)

$44.97Current Price $44.97
(50% off)50% off.
$90.00Comparable value $90.00
Baxter Boot (Men)
Eastland

Baxter Boot (Men)

$69.97Current Price $69.97
(48% off)48% off.
$135.00Comparable value $135.00
Heritage Western Boot (Men)
Ariat

Heritage Western Boot (Men)

$112.47Current Price $112.47
(40% off)40% off.
$189.95Comparable value $189.95
(347)
Walpath Waterproof Chukka Boot (Men)
Clarks®

Walpath Waterproof Chukka Boot (Men)

$99.97Current Price $99.97
(23% off)23% off.
$130.00Comparable value $130.00
Thomas Lace-Up Boot (Men)
Dockers®

Thomas Lace-Up Boot (Men)

$59.97Current Price $59.97
(36% off)36% off.
$95.00Comparable value $95.00
Jack Chukka Boot (Men)
New!
Eastland

Jack Chukka Boot (Men)

$99.97Current Price $99.97
(20% off)20% off.
$125.00Comparable value $125.00
(1)
Finn Plain Toe Boot (Men)
Eastland

Finn Plain Toe Boot (Men)

$44.97Current Price $44.97
(50% off)50% off.
$90.00Comparable value $90.00
(2)
Ethan 1955 Cap Toe Boot (Men)
Eastland

Ethan 1955 Cap Toe Boot (Men)

$99.99Current Price $99.99
(55% off)55% off.
$225.00Comparable value $225.00
Premium Waterproof Lace-Up Chukka Boot (Men)
New!
Timberland

Premium Waterproof Lace-Up Chukka Boot (Men)

$59.97Current Price $59.97
(60% off)60% off.
$150.00Comparable value $150.00
(41)
Forge Lace-Up Boot (Men)
Florsheim

Forge Lace-Up Boot (Men)

$109.97Current Price $109.97
(18% off)18% off.
$135.00Comparable value $135.00
Allagash Standard Derby Boot (Men)
Eastland

Allagash Standard Derby Boot (Men)

$99.97Current Price $99.97
(31% off)31% off.
$145.00Comparable value $145.00
Chamberlin Grand Chelsea Boot (Men)
Cole Haan

Chamberlin Grand Chelsea Boot (Men)

$129.97Current Price $129.97
(50% off)50% off.
$260.00Comparable value $260.00
(1)
Coldbay Waterproof 3-Eye Duck Shoe (Men)
New!
Sperry

Coldbay Waterproof 3-Eye Duck Shoe (Men)

$49.97Current Price $49.97
(61% off)61% off.
$130.00Comparable value $130.00
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)
Avenue Duck Boot (Men)
Sperry

Avenue Duck Boot (Men)

$59.97Current Price $59.97
(50% off)50% off.
$120.00Comparable value $120.00
(16)
Garfield Plain Toe Chukka Boot (Men)
Deer Stags

Garfield Plain Toe Chukka Boot (Men)

$64.97Current Price $64.97
(35% off)35% off.
$100.00Comparable value $100.00
Maplewalk Rise Boot (Men)
Clarks®

Maplewalk Rise Boot (Men)

$89.97Current Price $89.97
(25% off)25% off.
$120.00Comparable value $120.00
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