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Comfort Boots for Men

  • All Comfort
  • Boots
  • Dress Shoes
  • Loafers & Oxfords
  • Sneakers
143 items
'Lumber Up' Moc Toe Boot (Men)
Clear The Rack
Eastland

'Lumber Up' Moc Toe Boot (Men)

$26.97 – $99.97Current Price $26.97 to $99.97
(Extra 25% off select items)Includes extra 25% off select items.
$35.97 – $74.96Previous Price $35.97 to $74.96
$135.00 – $150.00Comparable value $135.00 to $150.00
(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
(82)
Only a few left
Cold Bay Duck Boot (Men)
New
Sperry

Cold Bay Duck Boot (Men)

$49.97Current Price $49.97
(58% off)58% off.
$120.00Comparable value $120.00
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)
Clifton Waterproof Chelsea Duck Boot (Men)
Sperry

Clifton Waterproof Chelsea Duck Boot (Men)

$49.97Current Price $49.97
(54% off)54% off.
$110.00Comparable value $110.00
(1)
Only a few left
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)
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
(22)
Wilder Western Boot (Men)
Ariat

Wilder Western Boot (Men)

$119.97Current Price $119.97
(52% off)52% off.
$249.95Comparable value $249.95
(29)
Wallabee Chukka Boot (Men)
New
Clarks® Originals

Wallabee Chukka Boot (Men)

$89.97Current Price $89.97
(43% off)43% off.
$160.00Comparable value $160.00
x John Deere Slip-Ins Waterproof Swamper Boot (Men)
New
SKECHERS

x John Deere Slip-Ins Waterproof Swamper Boot (Men)

$59.97Current Price $59.97
(55% off)55% off.
$135.00Comparable value $135.00
Only a few left
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
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)
Upton Chukka (Men)
Johnston & Murphy

Upton Chukka (Men)

$129.97Current Price $129.97
(27% off)27% off.
$179.00Comparable value $179.00
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)
Sting Western Boot (Men)
Ariat

Sting Western Boot (Men)

$179.97Current Price $179.97
(33% off)33% off.
$269.95Comparable value $269.95
(90)
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)
Kingham Waterproof Boot (Men)
Ariat

Kingham Waterproof Boot (Men)

$99.97Current Price $99.97
(45% off)45% off.
$184.95Comparable value $184.95
(22)
Gitano Genuine Shearling Lined Water Repellent Boot (Men)
Clear The Rack
Aquatalia

Gitano Genuine Shearling Lined Water Repellent Boot (Men)

$146.22Current Price $146.22
(Extra 25% off)Includes extra 25% off.
$194.96Previous Price $194.96
$625.00Comparable value $625.00
(3)
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)
Dylan Chelsea Boot (Men)
Dockers®

Dylan Chelsea 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)

$69.97Current Price $69.97
(41% off)41% off.
$120.00Comparable value $120.00
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
(44)
Only a few left
Tanglewood Cowboy Boot (Men)
New
Ariat

Tanglewood Cowboy Boot (Men)

$159.97Current Price $159.97
(44% off)44% off.
$289.95Comparable value $289.95
(16)
Wallaston Chukka Boot (Men)
Clear The Rack
Clarks®

Wallaston Chukka Boot (Men)

$44.97 – $79.97Current Price $44.97 to $79.97
(Extra 25% off select items)Includes extra 25% off select items.
$59.96Previous Price $59.96
$120.00Comparable value $120.00
(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
Sport Latigo Square Toe Roper Heel Boot (Men)
Ariat

Sport Latigo Square Toe Roper Heel Boot (Men)

$119.97Current Price $119.97
(29% off)29% off.
$169.95Comparable value $169.95
(23)
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)
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)
Enrico Chelsea Boot (Men)
Aquatalia

Enrico Chelsea Boot (Men)

$229.97Current Price $229.97
(58% off)58% off.
$550.00Comparable value $550.00
Cowpuncher Venttek Western Boot (Men)
Ariat

Cowpuncher Venttek Western Boot (Men)

$149.97Current Price $149.97
(42% off)42% off.
$259.95Comparable value $259.95
(35)
Only a few left
Futurity Royal Western Boot (Men)
Ariat

Futurity Royal Western Boot (Men)

$179.97Current Price $179.97
(40% off)40% off.
$299.95Comparable value $299.95
(3)
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
Walker Cowboy Boot (Men)
Ariat

Walker Cowboy Boot (Men)

$179.97Current Price $179.97
(28% off)28% off.
$249.95Comparable value $249.95
(2)
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
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
Brody Chelsea Boot (Men)
Clear The Rack
Johnston & Murphy

Brody Chelsea Boot (Men)

$37.49Current Price $37.49
(Extra 25% off)Includes extra 25% off.
$49.99Previous Price $49.99
$165.00Comparable value $165.00
(19)
Only a few left
'Seneca' Moc Toe Boot (Men)
Clear The Rack
Eastland

'Seneca' Moc Toe Boot (Men)

$56.22Current Price $56.22
(Extra 25% off)Includes extra 25% off.
$74.96Previous Price $74.96
$125.00Comparable value $125.00
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)
Downtown Stonewash Suede Cowboy Boot (Men)
Ariat

Downtown Stonewash Suede Cowboy Boot (Men)

$119.97Current Price $119.97
(50% off)50% off.
$239.95Comparable value $239.95
(22)
Renegade Western Boot (Men)
Ariat

Renegade Western Boot (Men)

$114.97Current Price $114.97
(50% off)50% off.
$229.95Comparable value $229.95
(37)
Only a few left
Neumel Shaggy Suede Chukka Boot (Men)
Clear The Rack
UGG®

Neumel Shaggy Suede Chukka Boot (Men)

$53.41Current Price $53.41
(Extra 25% off)Includes extra 25% off.
$71.22Previous Price $71.22
$150.00Comparable value $150.00
(2)
'Daily Double' Chelsea Boot (Men)
Clear The Rack
Eastland

'Daily Double' Chelsea Boot (Men)

$29.98 – $33.72Current Price $29.98 to $33.72
(Extra 25% off)Includes extra 25% off.
$39.98 – $44.97Previous Price $39.98 to $44.97
$125.00Comparable value $125.00
(8)
Speed Solo Waterproof Mid Hiking Sneaker (Men)
Merrell

Speed Solo Waterproof Mid Hiking Sneaker (Men)

$94.97Current Price $94.97
(40% off)40% off.
$160.00Comparable value $160.00
(5)
Forge Chelsea Boot (Men)
Clear The Rack
Florsheim

Forge Chelsea Boot (Men)

$28.86 – $61.85Current Price $28.86 to $61.85
(Extra 25% off)Includes extra 25% off.
$38.48 – $82.47Previous Price $38.48 to $82.47
$130.00Comparable value $130.00
(3)
Only a few left
Attleboro Chelsea Boot (Men)
Clear The Rack
Timberland

Attleboro Chelsea Boot (Men)

$37.49Current Price $37.49
(Extra 25% off)Includes extra 25% off.
$49.99Previous Price $49.99
$140.00Comparable value $140.00
(10)
Moc Toe Boot (Men)
Dockers®

Moc Toe Boot (Men)

$64.97Current Price $64.97
(31% off)31% off.
$95.00Comparable value $95.00
(6)
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
Denali Waterproof Plain Toe Boot - Wide Width Available
NUNN BUSH

Denali Waterproof Plain Toe Boot - Wide Width Available

$99.97Current Price $99.97
(16% off)16% off.
$120.00Comparable value $120.00
(1)
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)
Only a few left
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)
Noog Fly Boot (Men)
Fly London

Noog Fly Boot (Men)

$154.97Current Price $154.97
(42% off)42% off.
$270.00Comparable value $270.00
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
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
Camden Chelsea Boot (Men)
Dockers®

Camden Chelsea Boot (Men)

$59.99Current Price $59.99
(29% off)29% off.
$85.00Comparable value $85.00
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)
Standout Cowboy Boot (Men)
New
Ariat

Standout Cowboy Boot (Men)

$139.97Current Price $139.97
(46% off)46% off.
$259.95Comparable value $259.95
(22)
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
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)
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)
Only a few left
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)
Dustin Boot (Men)
Dockers®

Dustin Boot (Men)

$59.97Current Price $59.97
(36% off)36% off.
$95.00Comparable value $95.00
(5)
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
(11)
Walker Espresso Western Boot (Men)
Ariat

Walker Espresso Western Boot (Men)

$179.97Current Price $179.97
(28% off)28% off.
$249.95Comparable value $249.95
(2)
Herman Water Resistant Chelsea Boot (Men)
Eastland

Herman Water Resistant Chelsea Boot (Men)

$79.97Current Price $79.97
(40% off)40% off.
$135.00Comparable value $135.00
(3)
Only a few left
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)
Renegade Western Boot (Men)
Ariat

Renegade Western Boot (Men)

$119.97Current Price $119.97
(45% off)45% off.
$219.95Comparable value $219.95
(37)
Futurity Time Western Boot (Men)
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
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)
Only a few left
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
(15)
Only a few left
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)
Azzano Plain Toe Chelsea Boot (Men)
Clear The Rack
Florsheim

Azzano Plain Toe Chelsea Boot (Men)

$61.85Current Price $61.85
(Extra 25% off)Includes extra 25% off.
$82.47Previous Price $82.47
$145.00Comparable value $145.00
(2)
Only a few left
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