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Comfort Boots for Men

  • All Comfort
  • Boots
  • Dress Shoes
  • Loafers & Oxfords
  • Sneakers
143 items
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)
Futurity Champ Western Boot (Men)
New
Ariat

Futurity Champ Western Boot (Men)

$179.97Current Price $179.97
(37% off)37% off.
$289.95Comparable value $289.95
(21)
Standout Cowboy Boot (Men)
New
Ariat

Standout Cowboy Boot (Men)

$139.97Current Price $139.97
(46% off)46% off.
$259.95Comparable value $259.95
(21)
Walpath Waterproof Chukka Boot (Men)
New
Clarks®

Walpath Waterproof Chukka Boot (Men)

$99.97Current Price $99.97
(23% off)23% off.
$130.00Comparable value $130.00
(2)
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)
Sting Western Boot (Men)
Ariat

Sting Western Boot (Men)

$179.97Current Price $179.97
(33% off)33% off.
$269.95Comparable value $269.95
(81)
Dylan Chelsea Boot (Men)
Dockers®

Dylan Chelsea Boot (Men)

$59.97Current Price $59.97
(36% off)36% off.
$95.00Comparable value $95.00
(5)
Forge Lace-Up Boot (Men)
Florsheim

Forge Lace-Up Boot (Men)

$82.47Current Price $82.47
(38% off)38% off.
$135.00Comparable value $135.00
(1)
Only a few left
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
(50)
Truman Chelsea Boot (Men)
Dockers®

Truman Chelsea Boot (Men)

$59.97Current Price $59.97
(36% off)36% off.
$95.00Comparable value $95.00
(5)
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
(78)
'Seneca' Moc Toe Boot (Men)
Eastland

'Seneca' Moc Toe Boot (Men)

$39.98Current Price $39.98
(68% off)68% off.
$125.00Comparable value $125.00
New Markdown
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)
Otis II Chelsea Boot (Men)
NUNN BUSH

Otis II Chelsea Boot (Men)

$89.97Current Price $89.97
(18% off)18% off.
$110.00Comparable value $110.00
(1)
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
Classic Minimod Waterproof Wool Boot (Men)
UGG®

Classic Minimod Waterproof Wool Boot (Men)

$74.96Current Price $74.96
(62% off)62% off.
$200.00Comparable value $200.00
(18)
Only a few left
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)
Spitfire All Terrain Waterproof Chukka Boot (Men)
New
Ariat

Spitfire All Terrain Waterproof Chukka Boot (Men)

$89.97Current Price $89.97
(47% off)47% off.
$169.95Comparable value $169.95
(11)
Maplewalk Rise Boot (Men)
Clarks®

Maplewalk Rise Boot (Men)

$89.97Current Price $89.97
(25% off)25% off.
$120.00Comparable value $120.00
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)
Newmarket Chukka Boot (Men)
Timberland

Newmarket Chukka Boot (Men)

$58.48Current Price $58.48
(61% off)61% off.
$150.00Comparable value $150.00
(6)
Only a few left
Henson XC4 Waterproof Chukka Boot (Men)
Johnston & Murphy

Henson XC4 Waterproof Chukka Boot (Men)

$99.97Current Price $99.97
(49% off)49% off.
$199.00Comparable value $199.00
(18)
Moab 3 Waterproof Mid Hiking Boot (Men)
New
Merrell

Moab 3 Waterproof Mid Hiking Boot (Men)

$119.97Current Price $119.97
(40% off)40% off.
$200.00Comparable value $200.00
(45)
Herman Water Resistant Chelsea Boot (Men)
Eastland

Herman Water Resistant Chelsea Boot (Men)

$59.96 – $79.97Current Price $59.96 to $79.97
(Up to 55% off select items)Up to 55% off select items.
$135.00Comparable value $135.00
(3)
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
(25)
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)
Renegade Western Boot (Men)
New
Ariat

Renegade Western Boot (Men)

$114.97Current Price $114.97
(50% off)50% off.
$229.95Comparable value $229.95
(31)
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
(398)
Steadwell Dress Boot (Men)
Clarks®

Steadwell Dress Boot (Men)

$99.97Current Price $99.97
(23% off)23% off.
$130.00Comparable value $130.00
Only a few left
Walker Espresso Western Boot (Men)
New
Ariat

Walker Espresso Western Boot (Men)

$179.97Current Price $179.97
(28% off)28% off.
$249.95Comparable value $249.95
(2)
Chamberlain Cap Toe Boot (Men)
Cole Haan

Chamberlain Cap Toe Boot (Men)

$97.47Current Price $97.47
(68% off)68% off.
$310.00Comparable value $310.00
(1)
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
Belgrade Boot (Men)
Eastland

Belgrade Boot (Men)

$48.73Current Price $48.73
(65% off)65% off.
$140.00Comparable value $140.00
(1)
Only a few left
Dustin Boot (Men)
Dockers®

Dustin Boot (Men)

$59.97Current Price $59.97
(36% off)36% off.
$95.00Comparable value $95.00
(3)
Classic Mini Boot (Men)
UGG®

Classic Mini Boot (Men)

$129.97Current Price $129.97
(25% off)25% off.
$175.00Comparable value $175.00
(12)
Only a few left
Uptown Western Boot (Men)
Ariat

Uptown Western Boot (Men)

$149.97Current Price $149.97
(40% off)40% off.
$249.95Comparable value $249.95
(12)
Only a few left
Moc Toe Boot (Men)
Dockers®

Moc Toe Boot (Men)

$64.97Current Price $64.97
(31% off)31% off.
$95.00Comparable value $95.00
(6)
Speed Solo Mid Waterproof Hiking Boot (Men)
New
Merrell

Speed Solo Mid Waterproof Hiking Boot (Men)

$94.97Current Price $94.97
(40% off)40% off.
$160.00Comparable value $160.00
(5)
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
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)
Gitano Genuine Shearling Lined Water Repellent Boot (Men)
Aquatalia

Gitano Genuine Shearling Lined Water Repellent Boot (Men)

$142.98 – $194.96Current Price $142.98 to $194.96
(Up to 77% off)Up to 77% off.
$625.00Comparable value $625.00
New Markdown
(1)
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
(28)
'Daily Double' Chelsea Boot (Men)
Eastland

'Daily Double' Chelsea Boot (Men)

$39.98 – $44.97Current Price $39.98 to $44.97
(Up to 68% off)Up to 68% off.
$125.00Comparable value $125.00
New Markdown
(8)
Wild Thang Cowboy Boot (Men)
Ariat

Wild Thang Cowboy Boot (Men)

$119.97Current Price $119.97
(52% off)52% off.
$249.95Comparable value $249.95
(10)
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
(327)
Jack Chukka Boot (Men)
Eastland

Jack Chukka Boot (Men)

$99.97Current Price $99.97
(20% off)20% off.
$125.00Comparable value $125.00
(1)
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
Walker Cowboy Boot (Men)
Ariat

Walker Cowboy Boot (Men)

$179.97Current Price $179.97
(28% off)28% off.
$249.95Comparable value $249.95
(2)
Classic Mini Atherson Boot (Men)
UGG®

Classic Mini Atherson Boot (Men)

$109.97Current Price $109.97
(42% off)42% off.
$190.00Comparable value $190.00
(9)
Edwin Weatherproof Lace-Up Boot (Men)
Aquatalia

Edwin Weatherproof Lace-Up Boot (Men)

$179.96Current Price $179.96
(68% off)68% off.
$575.00Comparable value $575.00
New Markdown
Only a few left
Renegade Western Boot (Men)
Ariat

Renegade Western Boot (Men)

$119.97Current Price $119.97
(45% off)45% off.
$219.95Comparable value $219.95
(31)
Neumel Chukka Boot (Men)
UGG®

Neumel Chukka Boot (Men)

$99.97Current Price $99.97
(Up to 35% off)Up to 35% off.
$150.00 – $155.00Comparable value $150.00 to $155.00
(461)
Only a few left
Neumel Chelsea Boot (Men)
UGG®

Neumel Chelsea Boot (Men)

$99.97Current Price $99.97
(35% off)35% off.
$155.00Comparable value $155.00
(29)
Only a few left
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
Gustavo Zip Combat Boot (Men)
Aquatalia

Gustavo Zip Combat Boot (Men)

$168.98Current Price $168.98
(72% off)72% off.
$625.00Comparable value $625.00
New Markdown
(1)
Only a few left
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)
'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
Gender Inclusive Campfire Crafted Regenerate Water Resistant Boot
UGG®

Gender Inclusive Campfire Crafted Regenerate Water Resistant Boot

$129.97Current Price $129.97
(40% off)40% off.
$220.00Comparable value $220.00
(8)
Futurity Time Western Boot (Men)
New
Ariat

Futurity Time Western Boot (Men)

$149.97Current Price $149.97
(46% off)46% off.
$279.95Comparable value $279.95
(74)
Only a few left
Dax Waterproof Chelsea Boot (Men)
Bos. & Co.

Dax Waterproof Chelsea Boot (Men)

$124.97Current Price $124.97
(54% off)54% off.
$275.00Comparable value $275.00
(2)
Only a few left
Hayden Chukka Boot (Men)
UGG®

Hayden Chukka Boot (Men)

$99.97Current Price $99.97
(33% off)33% off.
$150.00Comparable value $150.00
(5)
Only a few left
Neumel Shaggy Suede Chukka Boot (Men)
UGG®

Neumel Shaggy Suede Chukka Boot (Men)

$71.22Current Price $71.22
(52% off)52% off.
$150.00Comparable value $150.00
(2)
Enrico Chelsea Boot (Men)
Aquatalia

Enrico Chelsea Boot (Men)

$229.97Current Price $229.97
(58% off)58% off.
$550.00Comparable value $550.00
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)
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)
Venture Daze Ultra Mini Boot (Men)
UGG®

Venture Daze Ultra Mini Boot (Men)

$109.97Current Price $109.97
(38% off)38% off.
$180.00Comparable value $180.00
(22)
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)

$129.97Current Price $129.97
(38% off)38% off.
$210.00Comparable value $210.00
(8)
Only a few left
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
(2)
Venture Daze Ultra Mini Genuine Shearling Platform Bootie (Women)
UGG®

Venture Daze Ultra Mini Genuine Shearling Platform Bootie (Women)

$109.97Current Price $109.97
(42% off)42% off.
$190.00Comparable value $190.00
(7)
Shasta Gore-Tex® Waterproof Boot (Women)
UGG®

Shasta Gore-Tex® Waterproof Boot (Women)

$299.97Current Price $299.97
(40% off)40% off.
$500.00Comparable value $500.00
(13)
Only a few left
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