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Comfort Boots for Men

  • All Comfort
  • Boots
  • Dress Shoes
  • Loafers & Oxfords
  • Sneakers
182 items
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
(1)
Avenue Duck Boot (Men)
Sperry

Avenue Duck Boot (Men)

$59.97Current Price $59.97
(50% off)50% off.
$120.00Comparable value $120.00
(16)
Gitano Genuine Shearling Lined Water Repellent Boot (Men)
Aquatalia

Gitano Genuine Shearling Lined Water Repellent Boot (Men)

$259.97Current Price $259.97
(58% off)58% off.
$625.00Comparable value $625.00
(1)
Heritage Western Boot (Men)
Ariat

Heritage Western Boot (Men)

$112.47Current Price $112.47
(40% off)40% off.
$189.95Comparable value $189.95
(348)
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
Karnak Water Resistant Moc Toe Boot (Men)
NUNN BUSH

Karnak Water Resistant Moc Toe Boot (Men)

$89.97Current Price $89.97
(18% off)18% off.
$110.00Comparable value $110.00
(3)
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
'Daily Double' Chelsea Boot (Men)
Eastland

'Daily Double' Chelsea Boot (Men)

$74.97Current Price $74.97
(40% off)40% off.
$125.00Comparable value $125.00
(8)
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)
Newmarket Chukka Boot (Men)
Timberland

Newmarket Chukka Boot (Men)

$89.97Current Price $89.97
(40% off)40% off.
$150.00Comparable value $150.00
(6)
'Lumber Up' Moc Toe Boot (Men)
Eastland

'Lumber Up' Moc Toe Boot (Men)

$74.97 – $99.97Current Price $74.97 to $99.97
(Up to 50% off select items)Up to 50% off select items.
$135.00 – $150.00Comparable value $135.00 to $150.00
(4)
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
(7)
Classic Minimod Waterproof Wool Boot (Men)
UGG®

Classic Minimod Waterproof Wool Boot (Men)

$99.97Current Price $99.97
(50% off)50% off.
$200.00Comparable value $200.00
(10)
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
Recon Lace Boot (Men)
Ariat

Recon Lace Boot (Men)

$139.97Current Price $139.97
(12% off)12% off.
$159.95Comparable value $159.95
(101)
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
Truman Chelsea Boot (Men)
Dockers®

Truman Chelsea Boot (Men)

$59.97Current Price $59.97
(36% off)36% off.
$95.00Comparable value $95.00
(1)
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)
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
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)
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
Cold Bay Duck Boot (Men)
Sperry

Cold Bay Duck Boot (Men)

$49.97Current Price $49.97
(61% off)61% off.
$130.00Comparable value $130.00
(22)
Moab 3 Vista Waterproof Mid Hiking Shoe (Men)
Merrell

Moab 3 Vista Waterproof Mid Hiking Shoe (Men)

$69.97Current Price $69.97
(53% off)53% off.
$150.00Comparable value $150.00
(42)
Sport Stratten Leather Boot (Men)
Ariat

Sport Stratten Leather Boot (Men)

$99.97Current Price $99.97
(47% off)47% off.
$189.95Comparable value $189.95
(51)
Only a few left
Moab 3 Mid Waterproof Hiking Shoe (Men)
Merrell

Moab 3 Mid Waterproof Hiking Shoe (Men)

$99.97Current Price $99.97
(41% off)41% off.
$170.00Comparable value $170.00
(365)
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
Sting Western Boot (Men)
Ariat

Sting Western Boot (Men)

$179.97Current Price $179.97
(33% off)33% off.
$269.95Comparable value $269.95
(56)
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
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
Edwin Weatherproof Lace-Up Boot (Men)
Aquatalia

Edwin Weatherproof Lace-Up Boot (Men)

$239.97Current Price $239.97
(58% off)58% off.
$575.00Comparable value $575.00
Excavate Water Resistant Moc Toe Boot (Men)
NUNN BUSH

Excavate Water Resistant Moc Toe Boot (Men)

$69.97Current Price $69.97
(26% off)26% off.
$95.00Comparable value $95.00
(4)
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
Calgary Chukka Boot (Men)
Dockers®

Calgary Chukka Boot (Men)

$69.97Current Price $69.97
(26% off)26% off.
$95.00Comparable value $95.00
Esmond Chukka Boot (Men)
Dockers®

Esmond Chukka Boot (Men)

$59.97Current Price $59.97
(36% off)36% off.
$95.00Comparable value $95.00
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)
Willie French Toe Western Boot (Men)
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
Jenson Chelsea Boot (Men)
Johnston & Murphy

Jenson Chelsea Boot (Men)

$209.97Current Price $209.97
(35% off)35% off.
$328.00Comparable value $328.00
(3)
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
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)
Edmundo Water Repellent Combat Boot (Men)
Aquatalia

Edmundo Water Repellent Combat Boot (Men)

$259.97Current Price $259.97
(58% off)58% off.
$625.00Comparable value $625.00
(3)
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)
Attleboro Mid Chukka Boot (Men)
Timberland

Attleboro Mid Chukka Boot (Men)

$69.97Current Price $69.97
(46% off)46% off.
$130.00Comparable value $130.00
(5)
Stump Jumper Boot (Men)
Ariat

Stump Jumper Boot (Men)

$119.97Current Price $119.97
(40% off)40% off.
$199.95Comparable value $199.95
(24)
Only a few left
Camden Chelsea Boot (Men)
Dockers®

Camden Chelsea Boot (Men)

$59.99Current Price $59.99
(29% off)29% off.
$85.00Comparable value $85.00
Charge Work Boot - Wide Width Available
Dr. Scholl's

Charge Work Boot - Wide Width Available

$84.97Current Price $84.97
(34% off)34% off.
$130.00Comparable value $130.00
(45)
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)
Euro Spring Mid Hiking Boot (Men)
New!
Timberland

Euro Spring Mid Hiking Boot (Men)

$69.97Current Price $69.97
(46% off)46% off.
$130.00Comparable value $130.00
Herman Water Resistant Chelsea Boot (Men)
Eastland

Herman Water Resistant Chelsea Boot (Men)

$59.97 – $79.97Current Price $59.97 to $79.97
(Up to 55% off select items)Up to 55% off select items.
$135.00Comparable value $135.00
(2)
Neumel Trailgazer Waterproof Boot (Men)
UGG®

Neumel Trailgazer Waterproof Boot (Men)

$79.97Current Price $79.97
(55% off)55% off.
$180.00Comparable value $180.00
(6)
Only a few left
Brutus Combat Boot (Men)
Camper

Brutus Combat Boot (Men)

$129.97Current Price $129.97
(40% off)40% off.
$220.00Comparable value $220.00
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
(4)
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
Lewis Chelsea Boot (Men)
Johnston & Murphy

Lewis Chelsea Boot (Men)

$69.97Current Price $69.97
(45% off)45% off.
$129.00Comparable value $129.00
(5)
Classic Mini Boot (Men)
UGG®

Classic Mini Boot (Men)

$89.97Current Price $89.97
(43% off)43% off.
$160.00Comparable value $160.00
(11)
Only a few left
Venture Daze Ultra Mini Boot (Men)
UGG®

Venture Daze Ultra Mini Boot (Men)

$99.97Current Price $99.97
(44% off)44% off.
$180.00Comparable value $180.00
(14)
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
Franz Gore-Tex® Boot (Men)
ara

Franz Gore-Tex® Boot (Men)

$109.97Current Price $109.97
(54% off)54% off.
$240.00Comparable value $240.00
Only a few left
Dylan Chelsea Boot (Men)
Dockers®

Dylan Chelsea Boot (Men)

$59.97Current Price $59.97
(36% off)36% off.
$95.00Comparable value $95.00
Avenue Waterproof Duck Boot (Men)
Sperry

Avenue Waterproof Duck Boot (Men)

$39.97Current Price $39.97
(66% off)66% off.
$120.00Comparable value $120.00
(1)
Brody Chukka Boot (Men)
Johnston & Murphy

Brody Chukka Boot (Men)

$109.97Current Price $109.97
(33% off)33% off.
$165.00Comparable value $165.00
(27)
Only a few left
Authentic Original Double Sole Chukka (Men)
New!
Sperry

Authentic Original Double Sole Chukka (Men)

$44.97Current Price $44.97
(65% off)65% off.
$130.00Comparable value $130.00
Only a few left
1912 Plain Toe Chelsea Boot (Men)
NUNN BUSH

1912 Plain Toe Chelsea Boot (Men)

$79.97Current Price $79.97
(27% off)27% off.
$110.00Comparable value $110.00
(2)
Tobias Lug Sole Boot (Men)
Dockers®

Tobias Lug Sole Boot (Men)

$59.97Current Price $59.97
(36% off)36% off.
$95.00Comparable value $95.00
Neumal Crafted Regenerate Water Resistant Chukka Boot (Men)
UGG®

Neumal Crafted Regenerate Water Resistant Chukka Boot (Men)

$99.97Current Price $99.97
(50% off)50% off.
$200.00Comparable value $200.00
(4)
Cold Bay Duck Boot (Men)
Sperry

Cold Bay Duck Boot (Men)

$39.97Current Price $39.97
(66% off)66% off.
$120.00Comparable value $120.00
(5)
Heritage Western Boot (Men)
Ariat

Heritage Western Boot (Men)

$104.97Current Price $104.97
(44% off)44% off.
$189.95Comparable value $189.95
(348)
Enrico Chelsea Boot (Men)
Aquatalia

Enrico Chelsea Boot (Men)

$229.97Current Price $229.97
(58% off)58% off.
$550.00Comparable value $550.00
Excavate Plain Toe Boot - Wide Width Available (Men)
NUNN BUSH

Excavate Plain Toe Boot - Wide Width Available (Men)

$59.97 – $64.97Current Price $59.97 to $64.97
(Up to 36% off)Up to 36% off.
$90.00 – $95.00Comparable value $90.00 to $95.00
(4)
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
Thomson Chukka Boot (Men)
Børn

Thomson Chukka Boot (Men)

$89.97Current Price $89.97
(30% off)30% off.
$130.00Comparable value $130.00
(25)
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)
Steadwell Dress Boot (Men)
Clarks®

Steadwell Dress Boot (Men)

$99.97Current Price $99.97
(23% off)23% off.
$130.00Comparable value $130.00
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