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Comfort Boots for Men

  • All Comfort
  • Boots
  • Dress Shoes
  • Loafers & Oxfords
  • Sneakers
138 items
Chalet Chelsea Boot (Men)
Florsheim

Chalet Chelsea Boot (Men)

$69.96Current Price $69.96
(51% off)51% off.
$145.00Comparable value $145.00
New Markdown
(121)
Lite Hybrid Chukka Boot (Men)
ECCO

Lite Hybrid Chukka Boot (Men)

$79.97Current Price $79.97
(42% off)42% off.
$140.00Comparable value $140.00
Boswell Chukka Boot (Men)
Johnston & Murphy

Boswell Chukka Boot (Men)

$49.98Current Price $49.98
(71% off)71% off.
$175.00Comparable value $175.00
New Markdown
(17)
Circuit Plain Toe Chukka Boot - Wide Width Available (Men)
NUNN BUSH

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

$41.22 – $54.97Current Price $41.22 to $54.97
(Up to 54% off select items)Up to 54% off select items.
$90.00Comparable value $90.00
(17)
Chase Plain Toe Chukka Boot - Wide Width Available (Men)
NUNN BUSH

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

$11.24 – $49.97Current Price $11.24 to $49.97
(Up to 88% off select items)Up to 88% off select items.
$95.00Comparable value $95.00
New Markdown
(14)
Excavate Plain Toe Boot - Wide Width Available (Men)
NUNN BUSH

Excavate Plain Toe Boot - Wide Width Available (Men)

$64.97Current Price $64.97
(Up to 31% off)Up to 31% off.
$90.00 – $95.00Comparable value $90.00 to $95.00
(4)
Tempo Sol Waterproof Hiking Boot (Men)
New
Merrell

Tempo Sol Waterproof Hiking Boot (Men)

$59.97Current Price $59.97
(25% off)25% off.
$80.00Comparable value $80.00
(1)
'Lookout' Moc Toe Boot (Men)
Ariat

'Lookout' Moc Toe Boot (Men)

$79.97Current Price $79.97
(50% off)50% off.
$159.95Comparable value $159.95
(70)
Shepton Easy Chelsea Boot (Men)
Clarks®

Shepton Easy Chelsea Boot (Men)

$64.98 – $94.97Current Price $64.98 to $94.97
(Up to 50% off select items)Up to 50% off select items.
$130.00Comparable value $130.00
New Markdown
Theo Chukka Boot (Men)
Børn

Theo Chukka Boot (Men)

$19.99 – $55.96Current Price $19.99 to $55.96
(Up to 84% off)Up to 84% off.
$130.00Comparable value $130.00
New Markdown
(13)
Esmond Chukka Boot (Men)
Dockers®

Esmond Chukka Boot (Men)

$59.97Current Price $59.97
(36% off)36% off.
$95.00Comparable value $95.00
(5)
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
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)
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)
Chalet Leather Cap Toe Boot (Men)
Florsheim

Chalet Leather Cap Toe Boot (Men)

$59.98Current Price $59.98
(61% off)61% off.
$155.00Comparable value $155.00
New Markdown
(23)
Wallabee FTR2 Moc Toe Chukka Boot (Men)
New
Clarks®

Wallabee FTR2 Moc Toe Chukka Boot (Men)

$79.97Current Price $79.97
(42% off)42% off.
$140.00Comparable value $140.00
Lockhart Mini Lug Suede Chelsea Boot (Men)
Nordstrom

Lockhart Mini Lug Suede Chelsea Boot (Men)

$49.97Current Price $49.97
(58% off)58% off.
$119.95Comparable value $119.95
(2)
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
(3)
Torhill Lo Chukka Boot (Men)
New
Clarks®

Torhill Lo Chukka Boot (Men)

$69.97Current Price $69.97
(46% off)46% off.
$130.00Comparable value $130.00
Truman Chelsea Boot (Men)
Dockers®

Truman Chelsea Boot (Men)

$59.97Current Price $59.97
(36% off)36% off.
$95.00Comparable value $95.00
(5)
Cold Bay Duck Boot (Men)
Sperry

Cold Bay Duck Boot (Men)

$49.97Current Price $49.97
(58% off)58% off.
$120.00Comparable value $120.00
Upton Chukka (Men)
Johnston & Murphy

Upton Chukka (Men)

$129.97Current Price $129.97
(27% off)27% off.
$179.00Comparable value $179.00
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
(5)
Motion Ledge Mid Hiking Boot (Men)
Timberland

Motion Ledge Mid Hiking Boot (Men)

$48.96Current Price $48.96
(59% off)59% off.
$120.00Comparable value $120.00
New Markdown
Moab Speed 2 Waterproof Hiking Boot (Men)
Merrell

Moab Speed 2 Waterproof Hiking Boot (Men)

$109.97Current Price $109.97
(42% off)42% off.
$190.00Comparable value $190.00
(31)
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)
Dylan Chelsea Boot (Men)
Dockers®

Dylan Chelsea Boot (Men)

$59.97Current Price $59.97
(36% off)36% off.
$95.00Comparable value $95.00
(5)
Bend Chelsea Boot (Men)
Birkenstock

Bend Chelsea Boot (Men)

$99.97Current Price $99.97
(41% off)41% off.
$170.00Comparable value $170.00
(1)
Slingshot Cowboy Boot (Men)
Ariat

Slingshot Cowboy Boot (Men)

$119.97Current Price $119.97
(50% off)50% off.
$239.95Comparable value $239.95
(119)
Esmond Plain Toe Chukka Boot (Men)
Dockers®

Esmond Plain Toe Chukka Boot (Men)

$59.97Current Price $59.97
(29% off)29% off.
$85.00Comparable value $85.00
(10)
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
(2)
Only a few left
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)
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
(11)
Barrett Almond Toe Boot (Men)
Ariat

Barrett Almond Toe Boot (Men)

$159.97Current Price $159.97
(38% off)38% off.
$259.95Comparable value $259.95
(5)
Dustin Boot (Men)
Dockers®

Dustin Boot (Men)

$59.97Current Price $59.97
(36% off)36% off.
$95.00Comparable value $95.00
(5)
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
(331)
Wallabee Genuine Calf Hair Chukka (Men)
New
Clarks®

Wallabee Genuine Calf Hair Chukka (Men)

$99.97Current Price $99.97
(44% off)44% off.
$180.00Comparable value $180.00
Grand Remix Chukka Boot (Men)
Cole Haan

Grand Remix Chukka Boot (Men)

$24.99 – $99.97Current Price $24.99 to $99.97
(Up to 89% off select items)Up to 89% off select items.
$220.00 – $230.00Comparable value $220.00 to $230.00
New Markdown
(15)
Only a few left
Ridgeback Round Toe Cowboy Boot (Men)
Ariat

Ridgeback Round Toe Cowboy Boot (Men)

$109.97Current Price $109.97
(50% off)50% off.
$219.95Comparable value $219.95
(10)
Kingham Waterproof Boot (Men)
Ariat

Kingham Waterproof Boot (Men)

$99.97Current Price $99.97
(45% off)45% off.
$184.95Comparable value $184.95
(22)
Downtown Western Boot (Men)
New
Ariat

Downtown Western Boot (Men)

$139.97Current Price $139.97
(46% off)46% off.
$259.95Comparable value $259.95
(21)
Ridgeback Oily Western Boot (Men)
New
Ariat

Ridgeback Oily Western Boot (Men)

$129.97Current Price $129.97
(40% off)40% off.
$219.95Comparable value $219.95
(38)
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
Grand Atlantic Chukka Boot - Wide Width Available (Men)
Cole Haan

Grand Atlantic Chukka Boot - Wide Width Available (Men)

$24.99Current Price $24.99
(87% off)87% off.
$200.00Comparable value $200.00
New Markdown
(43)
'Seneca' Moc Toe Boot (Men)
Eastland

'Seneca' Moc Toe Boot (Men)

$74.96Current Price $74.96
(40% off)40% off.
$125.00Comparable value $125.00
Telford Lace-Up Boot (Men)
Dockers®

Telford Lace-Up Boot (Men)

$59.97Current Price $59.97
(36% off)36% off.
$95.00Comparable value $95.00
(5)
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)
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
Spitfire Leather Chukka Boot (Men)
Ariat

Spitfire Leather Chukka Boot (Men)

$69.97Current Price $69.97
(50% off)50% off.
$139.95Comparable value $139.95
(53)
Premium 6-Inch Waterproof Patent Boot (Men)
New
Timberland

Premium 6-Inch Waterproof Patent Boot (Men)

$99.97Current Price $99.97
(52% off)52% off.
$210.00Comparable value $210.00
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)
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
(35)
Futurity Cashout Square Toe Boot (Men)
Ariat

Futurity Cashout Square Toe Boot (Men)

$159.97Current Price $159.97
(42% off)42% off.
$279.95Comparable value $279.95
(15)
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)
Wallaston Low Chukka Sneaker (Men)
Clarks®

Wallaston Low Chukka Sneaker (Men)

$84.97Current Price $84.97
(22% off)22% off.
$110.00Comparable value $110.00
Otto Chukka Boot - Wide Width Available (Men)
NUNN BUSH

Otto Chukka Boot - Wide Width Available (Men)

$11.24 – $79.97Current Price $11.24 to $79.97
(Up to 90% off select items)Up to 90% off select items.
$110.00 – $120.00Comparable value $110.00 to $120.00
New Markdown
(14)
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
Chamberlin Grand Water Resistant Chelsea Boot (Men)
Cole Haan

Chamberlin Grand Water Resistant Chelsea Boot (Men)

$97.47 – $119.97Current Price $97.47 to $119.97
(Up to 62% off select items)Up to 62% off select items.
$260.00Comparable value $260.00
(11)
Only a few left
Wexford Chelsea Boot (Men)
Ariat

Wexford Chelsea Boot (Men)

$99.97Current Price $99.97
(47% off)47% off.
$189.95Comparable value $189.95
(4)
Moc Toe Boot (Men)
Dockers®

Moc Toe Boot (Men)

$64.97Current Price $64.97
(31% off)31% off.
$95.00Comparable value $95.00
(6)
'Lumber Up' Moc Toe Boot (Men)
Eastland

'Lumber Up' Moc Toe Boot (Men)

$74.96 – $99.97Current Price $74.96 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
(5)
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
(6)
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
(3)
Downtown Western Boot (Men)
Ariat

Downtown Western Boot (Men)

$139.97Current Price $139.97
(46% off)46% off.
$259.95Comparable value $259.95
(26)
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)
Futurity Champ Western Boot (Men)
Ariat

Futurity Champ Western Boot (Men)

$179.97Current Price $179.97
(37% off)37% off.
$289.95Comparable value $289.95
(24)
x John Deere Lace-Up Boot (Men)
New
SKECHERS

x John Deere Lace-Up Boot (Men)

$59.97Current Price $59.97
(55% off)55% off.
$135.00Comparable value $135.00
Moab 3 Waterproof Mid Hiking Boot (Men)
Merrell

Moab 3 Waterproof Mid Hiking Boot (Men)

$119.97Current Price $119.97
(40% off)40% off.
$200.00Comparable value $200.00
(46)
Standout Cowboy Boot (Men)
Ariat

Standout Cowboy Boot (Men)

$139.97Current Price $139.97
(46% off)46% off.
$259.95Comparable value $259.95
(22)
Chamberlin Grand Chukka Boot (Men)
Cole Haan

Chamberlin Grand Chukka Boot (Men)

$97.47Current Price $97.47
(66% off)66% off.
$290.00Comparable value $290.00
(10)
Only a few left
Quickdraw Western Boot (Men)
New
Ariat

Quickdraw Western Boot (Men)

$119.97Current Price $119.97
(50% off)50% off.
$239.95Comparable value $239.95
(103)
Oakwood Cowboy Boot (Men)
New
Ariat

Oakwood Cowboy Boot (Men)

$139.97Current Price $139.97
(46% off)46% off.
$259.95Comparable value $259.95
(78)
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