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Comfort Boots for Men

  • All Comfort
  • Boots
  • Dress Shoes
  • Loafers & Oxfords
  • Sneakers
127 items
Lite Hybrid Chukka Boot (Men)
New
ECCO

Lite Hybrid Chukka Boot (Men)

$79.97Current Price $79.97
(42% off)42% off.
$140.00Comparable value $140.00
Moab Speed 2 Waterproof Hiking Boot (Men)
New
Merrell

Moab Speed 2 Waterproof Hiking Boot (Men)

$109.97Current Price $109.97
(42% off)42% off.
$190.00Comparable value $190.00
Motion Ledge Mid Hiking Boot (Men)
Timberland

Motion Ledge Mid Hiking Boot (Men)

$69.97Current Price $69.97
(41% off)41% off.
$120.00Comparable value $120.00
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)
Circuit Rockridge Western Boot (Men)
New
Ariat

Circuit Rockridge Western Boot (Men)

$159.97Current Price $159.97
(44% off)44% off.
$289.95Comparable value $289.95
(24)
Tempo Sol Waterproof Mid Top Hiking Boot (Men)
New
Merrell

Tempo Sol Waterproof Mid Top Hiking Boot (Men)

$79.97Current Price $79.97
(20% off)20% off.
$100.00Comparable value $100.00
Weltridge Side Zip Boot (Men)
Clarks®

Weltridge Side Zip Boot (Men)

$42.73 – $94.97Current Price $42.73 to $94.97
(Extra 40% off select items)Includes extra 40% off select items.
$71.22Previous Price $71.22
$130.00Comparable value $130.00
Price Drop
(2)
Morse GRANDFØAM Chukka Boot (Men)
Cole Haan

Morse GRANDFØAM Chukka Boot (Men)

$50.68 – $129.97Current Price $50.68 to $129.97
(Extra 40% off select items)Includes extra 40% off select items.
$84.48 – $97.47Previous Price $84.48 to $97.47
$220.00Comparable value $220.00
Price Drop
(3)
Enrico Chelsea Boot (Men)
Aquatalia

Enrico Chelsea Boot (Men)

$229.97Current Price $229.97
(58% off)58% off.
$550.00Comparable value $550.00
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)
Grand Atlantic Chukka Boot - Wide Width Available (Men)
Cole Haan

Grand Atlantic Chukka Boot - Wide Width Available (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
(43)
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
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
Moab 3 Mid Waterproof Hiking Shoe (Men)
New
Merrell

Moab 3 Mid Waterproof Hiking Shoe (Men)

$99.97Current Price $99.97
(41% off)41% off.
$170.00Comparable value $170.00
(394)
Standout Cowboy Boot (Men)
New
Ariat

Standout Cowboy Boot (Men)

$149.97Current Price $149.97
(42% off)42% off.
$259.95Comparable value $259.95
(21)
Fortino Water Repellent Boot (Men)
Aquatalia

Fortino Water Repellent Boot (Men)

$259.97Current Price $259.97
(58% off)58% off.
$625.00Comparable value $625.00
(1)
2.Zerogrand Chukka Boot (Men)
Cole Haan

2.Zerogrand Chukka Boot (Men)

$44.97 – $99.97Current Price $44.97 to $99.97
(Extra 40% off select items)Includes extra 40% off select items.
$74.96Previous Price $74.96
$338.00Comparable value $338.00
Price Drop
(403)
Hustler Narrow Cutter Toe Cowboy Boot (Men)
New
Ariat

Hustler Narrow Cutter Toe Cowboy Boot (Men)

$139.97Current Price $139.97
(44% off)44% off.
$249.95Comparable value $249.95
(12)
Chalet Chelsea Boot (Men)
Florsheim

Chalet Chelsea Boot (Men)

$99.97Current Price $99.97
(31% off)31% off.
$145.00Comparable value $145.00
(120)
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
(4)
Gustavo Zip Combat Boot (Men)
Aquatalia

Gustavo Zip Combat Boot (Men)

$116.97 – $259.97Current Price $116.97 to $259.97
(Extra 40% off select items)Includes extra 40% off select items.
$194.96Previous Price $194.96
$625.00Comparable value $625.00
Price Drop
(1)
Wallaston Chukka Boot (Men)
Clarks®

Wallaston Chukka Boot (Men)

$35.97 – $79.97Current Price $35.97 to $79.97
(Extra 40% off select items)Includes extra 40% off select items.
$59.96Previous Price $59.96
$120.00Comparable value $120.00
Price Drop
(2)
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)
Only a few left
Slingshot Cowboy Boot (Men)
New
Ariat

Slingshot Cowboy Boot (Men)

$119.97Current Price $119.97
(50% off)50% off.
$239.95Comparable value $239.95
(110)
Bodie Cowboy Boot (Men)
New
Ariat

Bodie Cowboy Boot (Men)

$99.97Current Price $99.97
(44% off)44% off.
$179.95Comparable value $179.95
(9)
Neumel Chelsea Boot (Men)
UGG®

Neumel Chelsea Boot (Men)

$89.97Current Price $89.97
(35% off)35% off.
$140.00Comparable value $140.00
(29)
Speed Solo Waterproof Mid Hiking Sneaker (Men)
New
Merrell

Speed Solo Waterproof Mid Hiking Sneaker (Men)

$94.97Current Price $94.97
(40% off)40% off.
$160.00Comparable value $160.00
(5)
Downtown Western Boot (Men)
New
Ariat

Downtown Western Boot (Men)

$149.97Current Price $149.97
(42% off)42% off.
$259.95Comparable value $259.95
(19)
Downtown Western Boot (Men)
Ariat

Downtown Western Boot (Men)

$139.97Current Price $139.97
(46% off)46% off.
$259.95Comparable value $259.95
(22)
Pix Combat Boot (Men)
Camper

Pix Combat Boot (Men)

$124.97Current Price $124.97
(35% off)35% off.
$195.00Comparable value $195.00
Only a few left
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
Spitfire Leather Chukka Boot (Men)
New
Ariat

Spitfire Leather Chukka Boot (Men)

$69.97Current Price $69.97
(50% off)50% off.
$139.95Comparable value $139.95
(46)
Craftwell Lace-Up Boot (Men)
Clarks®

Craftwell Lace-Up Boot (Men)

$79.97Current Price $79.97
(27% off)27% off.
$110.00Comparable value $110.00
Brody Chelsea Boot (Men)
Johnston & Murphy

Brody Chelsea Boot (Men)

$69.97Current Price $69.97
(57% off)57% off.
$165.00Comparable value $165.00
(19)
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)
Spitfire Leather Chukka Boot (Men)
Ariat

Spitfire Leather Chukka Boot (Men)

$59.97Current Price $59.97
(53% off)53% off.
$129.95Comparable value $129.95
(320)
'Lookout' Moc Toe Boot (Men)
New
Ariat

'Lookout' Moc Toe Boot (Men)

$79.97Current Price $79.97
(50% off)50% off.
$159.95Comparable value $159.95
(69)
Avenue Duck Boot (Men)
Sperry

Avenue Duck Boot (Men)

$26.98Current Price $26.98
(Extra 40% off)Includes extra 40% off.
$44.97Previous Price $44.97
$120.00Comparable value $120.00
Price Drop
(20)
Chamberlin Grand Chukka Boot (Men)
Cole Haan

Chamberlin Grand Chukka Boot (Men)

$58.48 – $129.97Current Price $58.48 to $129.97
(Extra 40% off select items)Includes extra 40% off select items.
$97.47Previous Price $97.47
$290.00Comparable value $290.00
Price Drop
(7)
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
(15)
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
Maplewalk Rise Boot (Men)
Clarks®

Maplewalk Rise Boot (Men)

$40.48 – $89.97Current Price $40.48 to $89.97
(Extra 40% off select items)Includes extra 40% off select items.
$67.47Previous Price $67.47
$120.00Comparable value $120.00
Price Drop
'Lumber Up' Moc Toe Boot (Men)
Eastland

'Lumber Up' Moc Toe Boot (Men)

$44.97 – $99.97Current Price $44.97 to $99.97
(Extra 40% off select items)Includes extra 40% off select items.
$74.96 – $89.96Previous Price $74.96 to $89.96
$135.00 – $150.00Comparable value $135.00 to $150.00
Price Drop
(4)
Spitfire All Terrain Waterproof Chukka Boot (Men)
Ariat

Spitfire All Terrain Waterproof Chukka Boot (Men)

$89.97Current Price $89.97
(47% off)47% off.
$169.95Comparable value $169.95
(9)
Only a few left
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
Classic Mini Atherson Boot (Men)
UGG®

Classic Mini Atherson Boot (Men)

$69.96Current Price $69.96
(63% off)63% off.
$190.00Comparable value $190.00
(9)
Only a few left
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)
Boswell Chukka Boot (Men)
Johnston & Murphy

Boswell Chukka Boot (Men)

$40.48 – $89.97Current Price $40.48 to $89.97
(Extra 40% off select items)Includes extra 40% off select items.
$67.47Previous Price $67.47
$175.00Comparable value $175.00
Price Drop
(13)
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)
Barrett Almond Toe Boot (Men)
New
Ariat

Barrett Almond Toe Boot (Men)

$159.97Current Price $159.97
(38% off)38% off.
$259.95Comparable value $259.95
(4)
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)
Wallaston Low Chukka Boot (Men)
Clarks®

Wallaston Low Chukka Boot (Men)

$84.97Current Price $84.97
(22% off)22% off.
$110.00Comparable value $110.00
(2)
Downtown Stonewash Suede Cowboy Boot (Men)
New
Ariat

Downtown Stonewash Suede Cowboy Boot (Men)

$119.97Current Price $119.97
(50% off)50% off.
$239.95Comparable value $239.95
(20)
Walker Cowboy Boot (Men)
New
Ariat

Walker Cowboy Boot (Men)

$179.97Current Price $179.97
(28% off)28% off.
$249.95Comparable value $249.95
Hustler Western Boot (Men)
New
Ariat

Hustler Western Boot (Men)

$129.97Current Price $129.97
(48% off)48% off.
$249.95Comparable value $249.95
(12)
Only a few left
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
Ridgeback Round Toe Cowboy Boot (Men)
New
Ariat

Ridgeback Round Toe Cowboy Boot (Men)

$109.97Current Price $109.97
(50% off)50% off.
$219.95Comparable value $219.95
(9)
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)
Sting Western Boot (Men)
Ariat

Sting Western Boot (Men)

$179.97Current Price $179.97
(33% off)33% off.
$269.95Comparable value $269.95
(76)
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)
Sting Western Boot (Men)
Ariat

Sting Western Boot (Men)

$139.97Current Price $139.97
(50% off)50% off.
$279.95Comparable value $279.95
(77)
Azzano Plain Toe Chukka Boot (Men)
Florsheim

Azzano Plain Toe Chukka 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
Only a few left
Sport Stratten Leather Boot (Men)
New
Ariat

Sport Stratten Leather Boot (Men)

$99.97Current Price $99.97
(47% off)47% off.
$189.95Comparable value $189.95
(74)
Kingham Waterproof Boot (Men)
New
Ariat

Kingham Waterproof Boot (Men)

$99.97Current Price $99.97
(45% off)45% off.
$184.95Comparable value $184.95
(22)
Karnak Water Resistant Plain Toe Boot (Men)
NUNN BUSH

Karnak Water Resistant Plain Toe Boot (Men)

$89.97Current Price $89.97
(18% off)18% off.
$110.00Comparable value $110.00
Venture Daze Ultra Mini Boot (Men)
UGG®

Venture Daze Ultra Mini Boot (Men)

$74.96Current Price $74.96
(58% off)58% off.
$180.00Comparable value $180.00
(21)
Sidestrike West Glory Cowboy Boot (Men)
New
Ariat

Sidestrike West Glory Cowboy Boot (Men)

$179.97Current Price $179.97
(40% off)40% off.
$299.95Comparable value $299.95
(46)
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)
Neumel High Weather Hybrid Waterproof Boot (Men)
UGG®

Neumel High Weather Hybrid Waterproof Boot (Men)

$64.98Current Price $64.98
(69% off)69% off.
$210.00Comparable value $210.00
(8)
Only a few left
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)
Lincoln Chukka (Men)
Børn

Lincoln Chukka (Men)

$40.48 – $89.97Current Price $40.48 to $89.97
(Extra 40% off select items)Includes extra 40% off select items.
$67.47Previous Price $67.47
$155.00Comparable value $155.00
Price Drop
(7)
Only a few left
Sport Square Toe Western Boot (Men)
Ariat

Sport Square Toe Western Boot (Men)

$119.97Current Price $119.97
(36% off)36% off.
$189.95Comparable value $189.95
(22)
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