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Comfort Boots for Men

  • All Comfort
  • Boots
  • Dress Shoes
  • Loafers & Oxfords
  • Sneakers
189 items
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
(4)
Attleboro Chelsea Boot (Men)
Upgrade to get by Christmas
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)
Morse GRANDFØAM Chukka Boot (Men)
Cole Haan

Morse GRANDFØAM Chukka Boot (Men)

$129.97Current Price $129.97
(40% off)40% off.
$220.00Comparable value $220.00
Boswell Chukka Boot (Men)
Upgrade to get by Christmas
Johnston & Murphy

Boswell Chukka Boot (Men)

$89.97Current Price $89.97
(48% off)48% off.
$175.00Comparable value $175.00
(10)
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
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
(20)
Burleigh Chukka (Men)
UGG®

Burleigh Chukka (Men)

$89.97Current Price $89.97
(43% off)43% off.
$160.00Comparable value $160.00
(14)
Only a few left
Chalet Chelsea Boot (Men)
Florsheim

Chalet Chelsea Boot (Men)

$99.97Current Price $99.97
(31% off)31% off.
$145.00Comparable value $145.00
(110)
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
(53)
Only a few left
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
(393)
Theo Chukka Boot (Men)
Upgrade to get by Christmas
Børn

Theo Chukka Boot (Men)

$79.97Current Price $79.97
(38% off)38% off.
$130.00Comparable value $130.00
(5)
Chamberlin Grand Chukka Boot (Men)
Upgrade to get by Christmas
Cole Haan

Chamberlin Grand Chukka Boot (Men)

$129.97Current Price $129.97
(55% off)55% off.
$290.00Comparable value $290.00
(1)
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
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
Willie French Toe Western Boot (Men)
Upgrade to get by Christmas
Ariat

Willie French Toe Western Boot (Men)

$149.97Current Price $149.97
(40% off)40% off.
$249.95Comparable value $249.95
(6)
Only a few left
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)
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
Brutus Trek Waterproof Chelsea Boot (Men)
Camper

Brutus Trek Waterproof Chelsea Boot (Men)

$164.97 – $169.97Current Price $164.97 to $169.97
(35% off)35% off.
$255.00 – $265.00Comparable value $255.00 to $265.00
(3)
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
(27)
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)
Wallaston Low Chukka Boot (Men)
New!
Clarks®

Wallaston Low Chukka Boot (Men)

$84.97Current Price $84.97
(22% off)22% off.
$110.00Comparable value $110.00
Newmark Grand Chelsea Boot (Men)
Upgrade to get by Christmas
Cole Haan

Newmark Grand Chelsea Boot (Men)

$129.97Current Price $129.97
(63% off)63% off.
$360.00Comparable value $360.00
Truman Chelsea Boot (Men)
Dockers®

Truman Chelsea Boot (Men)

$59.97Current Price $59.97
(36% off)36% off.
$95.00Comparable value $95.00
(1)
Neumel Boot (Men)
UGG®

Neumel Boot (Men)

$109.97Current Price $109.97
(26% off)26% off.
$150.00Comparable value $150.00
(7)
Only a few left
Newmarket Chukka Boot (Men)
Upgrade to get by Christmas
Timberland

Newmarket Chukka Boot (Men)

$89.97Current Price $89.97
(40% off)40% off.
$150.00Comparable value $150.00
(5)
Seth Chukka Boot (Men)
Børn

Seth Chukka Boot (Men)

$89.97Current Price $89.97
(35% off)35% off.
$140.00Comparable value $140.00
(7)
Eli Suede Chukka Boot (Men)
Upgrade to get by Christmas
Børn

Eli Suede Chukka Boot (Men)

$89.97Current Price $89.97
(30% off)30% off.
$130.00Comparable value $130.00
(1)
Azzano Plain Toe Chelsea Boot (Men)
Florsheim

Azzano Plain Toe Chelsea Boot (Men)

$109.97Current Price $109.97
(24% off)24% off.
$145.00Comparable value $145.00
Chamberlain Cap Toe Boot (Men)
Cole Haan

Chamberlain Cap Toe Boot (Men)

$129.97Current Price $129.97
(58% off)58% off.
$310.00Comparable value $310.00
(1)
Heritage Western Boot (Men)
Upgrade to get by Christmas
Ariat

Heritage Western Boot (Men)

$149.97Current Price $149.97
(21% off)21% off.
$189.95Comparable value $189.95
(347)
Sting Western Boot (Men)
Upgrade to get by Christmas
Ariat

Sting Western Boot (Men)

$179.97Current Price $179.97
(33% off)33% off.
$269.95Comparable value $269.95
(55)
Walpath Waterproof Chelsea Boot (Men)
New!
Clarks®

Walpath Waterproof Chelsea Boot (Men)

$99.97Current Price $99.97
(23% off)23% off.
$130.00Comparable value $130.00
Attleboro Mid Chukka Boot (Men)
Upgrade to get by Christmas
Timberland

Attleboro Mid Chukka Boot (Men)

$69.97Current Price $69.97
(46% off)46% off.
$130.00Comparable value $130.00
(5)
Grand Atlantic Chelsea Boot (Men)
Cole Haan

Grand Atlantic Chelsea Boot (Men)

$99.97Current Price $99.97
(50% off)50% off.
$200.00Comparable value $200.00
(2)
Killington Trekker Mid Boot (Men)
Upgrade to get by Christmas
Timberland

Killington Trekker Mid Boot (Men)

$69.97Current Price $69.97
(50% off)50% off.
$140.00Comparable value $140.00
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)
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)
Emmett Waterproof Snow Boot (Men)
UGG®

Emmett Waterproof Snow Boot (Men)

$79.97Current Price $79.97
(46% off)46% off.
$150.00Comparable value $150.00
(116)
Burleigh Chelsea Boot (Men)
UGG®

Burleigh Chelsea Boot (Men)

$99.97Current Price $99.97
(44% off)44% off.
$180.00Comparable value $180.00
(11)
Only a few left
Moab 3 Mid Waterproof Hiking Shoe (Men)
New!
Merrell

Moab 3 Mid Waterproof Hiking Shoe (Men)

$89.97Current Price $89.97
(47% off)47% off.
$170.00Comparable value $170.00
(362)
Upton Chukka Boot (Men)
Upgrade to get by Christmas
Johnston & Murphy

Upton Chukka Boot (Men)

$69.97Current Price $69.97
(58% off)58% off.
$169.00Comparable value $169.00
(18)
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 Woodbury Waterproof Boot (Men)
Upgrade to get by Christmas
Cole Haan

Grand Woodbury Waterproof Boot (Men)

$144.97Current Price $144.97
(42% off)42% off.
$250.00Comparable value $250.00
(2)
Only a few left
Fortino Water Repellent Boot (Men)
Upgrade to get by Christmas
Aquatalia

Fortino Water Repellent Boot (Men)

$259.97Current Price $259.97
(58% off)58% off.
$625.00Comparable value $625.00
(1)
Hutson Plain Toe Boot (Men)
Upgrade to get by Christmas
Johnston & Murphy

Hutson Plain Toe Boot (Men)

$99.97Current Price $99.97
(40% off)40% off.
$169.00Comparable value $169.00
(2)
Eli Chelsea Boot (Men)
New!
Børn

Eli Chelsea Boot (Men)

$89.97Current Price $89.97
(30% off)30% off.
$130.00Comparable value $130.00
(6)
Rockaway Waterproof Boot (Men)
Upgrade to get by Christmas
Timberland

Rockaway Waterproof Boot (Men)

$89.97Current Price $89.97
(35% off)35% off.
$140.00Comparable value $140.00
Only a few left
'Lumber Up' Moc Toe Boot (Men)
Upgrade to get by Christmas
Eastland

'Lumber Up' Moc Toe Boot (Men)

$79.97 – $99.97Current Price $79.97 to $99.97
(Up to 40% off)Up to 40% off.
$135.00 – $150.00Comparable value $135.00 to $150.00
(4)
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)
Moab 3 Vista Waterproof Mid Hiking Shoe (Men)
New!
Merrell

Moab 3 Vista Waterproof Mid Hiking Shoe (Men)

$69.97Current Price $69.97
(53% off)53% off.
$150.00Comparable value $150.00
(41)
Chimney Pond Chelsea Boot (Men)
Upgrade to get by Christmas
Eastland

Chimney Pond Chelsea Boot (Men)

$99.97Current Price $99.97
(31% off)31% off.
$145.00Comparable value $145.00
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)
Ruvo Chelsea Boot (Men)
Florsheim

Ruvo Chelsea Boot (Men)

$109.97Current Price $109.97
(26% off)26% off.
$150.00Comparable value $150.00
(21)
Jenson Chelsea Boot (Men)
Upgrade to get by Christmas
Johnston & Murphy

Jenson Chelsea Boot (Men)

$209.97Current Price $209.97
(35% off)35% off.
$328.00Comparable value $328.00
(3)
Edwin Weatherproof Lace-Up Boot (Men)
Upgrade to get by Christmas
Aquatalia

Edwin Weatherproof Lace-Up Boot (Men)

$239.97Current Price $239.97
(58% off)58% off.
$575.00Comparable value $575.00
Jack Chukka Boot (Men)
Eastland

Jack Chukka Boot (Men)

$89.97Current Price $89.97
(28% off)28% off.
$125.00Comparable value $125.00
(1)
Nalukai Kala Moc Toe Boot (Men)
OluKai

Nalukai Kala Moc Toe Boot (Men)

$69.97Current Price $69.97
(50% off)50% off.
$140.00Comparable value $140.00
(1)
Only a few left
Classic Mini Atherson Boot (Men)
UGG®

Classic Mini Atherson Boot (Men)

$99.97Current Price $99.97
(47% off)47% off.
$190.00Comparable value $190.00
(4)
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
(59)
Enrico Chelsea Boot (Men)
Aquatalia

Enrico Chelsea Boot (Men)

$229.97Current Price $229.97
(58% off)58% off.
$550.00Comparable value $550.00
Britton Road Waterproof Boot (Men)
Upgrade to get by Christmas
Timberland

Britton Road Waterproof Boot (Men)

$79.97Current Price $79.97
(57% off)57% off.
$190.00Comparable value $190.00
(21)
Westmore Chukka Boot (Men)
Upgrade to get by Christmas
Timberland

Westmore Chukka Boot (Men)

$69.97Current Price $69.97
(36% off)36% off.
$110.00Comparable value $110.00
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)
Newmarket Mid Lace Up Boot (Men)
Upgrade to get by Christmas
Timberland

Newmarket Mid Lace Up Boot (Men)

$79.97Current Price $79.97
(46% off)46% off.
$150.00Comparable value $150.00
(4)
Classic Mini Boot (Men)
UGG®

Classic Mini Boot (Men)

$89.97Current Price $89.97
(43% off)43% off.
$160.00Comparable value $160.00
(9)
Only a few left
Grand Atlantic Chukka Boot - Wide Width Available (Men)
Upgrade to get by Christmas
Cole Haan

Grand Atlantic Chukka Boot - Wide Width Available (Men)

$99.97Current Price $99.97
(50% off)50% off.
$200.00Comparable value $200.00
(38)
Lincoln Chukka (Men)
Børn

Lincoln Chukka (Men)

$89.97Current Price $89.97
(41% off)41% off.
$155.00Comparable value $155.00
(4)
Emmett Chelsea Boot (Men)
Clarks®

Emmett Chelsea Boot (Men)

$79.97 – $89.97Current Price $79.97 to $89.97
(Up to 27% off)Up to 27% off.
$110.00 – $120.00Comparable value $110.00 to $120.00
Gitano Genuine Shearling Lined Water Repellent Boot (Men)
Upgrade to get by Christmas
Aquatalia

Gitano Genuine Shearling Lined Water Repellent Boot (Men)

$259.97Current Price $259.97
(58% off)58% off.
$625.00Comparable value $625.00
(1)
Sport Patriot Cowboy Boot (Men)
Upgrade to get by Christmas
Ariat

Sport Patriot Cowboy Boot (Men)

$99.97Current Price $99.97
(41% off)41% off.
$169.95Comparable value $169.95
(290)
Only a few left
Henson XC4 Waterproof Chukka Boot (Men)
Johnston & Murphy

Henson XC4 Waterproof Chukka Boot (Men)

$99.97 – $109.97Current Price $99.97 to $109.97
(Up to 49% off)Up to 49% off.
$199.00Comparable value $199.00
(18)
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