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Comfort Boots for Men

  • All Comfort
  • Boots
  • Dress Shoes
  • Loafers & Oxfords
  • Sneakers
133 items
Newmark Grand Chelsea Boot (Men)
Cole Haan

Newmark Grand Chelsea Boot (Men)

$58.48Current Price $58.48
(Extra 40% off)Includes extra 40% off.
$97.47Previous Price $97.47
$360.00Comparable value $360.00
Price Drop
(1)
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
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
(4)
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)
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
(1)
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
(5)
Theo Chukka Boot (Men)
Børn

Theo Chukka Boot (Men)

$33.57 – $35.97Current Price $33.57 to $35.97
(Extra 40% off)Includes extra 40% off.
$55.96 – $59.96Previous Price $55.96 to $59.96
$130.00Comparable value $130.00
Price Drop
(9)
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
(12)
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)
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
(42)
Gustavo Zip Combat Boot (Men)
Aquatalia

Gustavo Zip Combat Boot (Men)

$101.38 – $259.97Current Price $101.38 to $259.97
(Extra 40% off select items)Includes extra 40% off select items.
$168.98Previous Price $168.98
$625.00Comparable value $625.00
Price Drop
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)
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)
Downtown Western Boot (Men)
Ariat

Downtown Western Boot (Men)

$129.97Current Price $129.97
(50% off)50% off.
$259.95Comparable value $259.95
(22)
Attleboro Chelsea Boot (Men)
Timberland

Attleboro Chelsea Boot (Men)

$29.99Current Price $29.99
(Extra 40% off)Includes extra 40% off.
$49.99Previous Price $49.99
$130.00 – $140.00Comparable value $130.00 to $140.00
Price Drop
(8)
'Lumber Up' Moc Toe Boot (Men)
Eastland

'Lumber Up' Moc Toe Boot (Men)

$35.97 – $99.97Current Price $35.97 to $99.97
(Extra 40% off select items)Includes extra 40% off select items.
$59.96 – $89.96Previous Price $59.96 to $89.96
$135.00 – $150.00Comparable value $135.00 to $150.00
Price Drop
(4)
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
(3)
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)
Eli Suede Chukka Boot (Men)
Børn

Eli Suede Chukka Boot (Men)

$35.08 – $40.48Current Price $35.08 to $40.48
(Extra 40% off)Includes extra 40% off.
$58.48 – $67.47Previous Price $58.48 to $67.47
$130.00Comparable value $130.00
Price Drop
(3)
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)
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)
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)
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
Chalet Chelsea Boot (Men)
Florsheim

Chalet Chelsea Boot (Men)

$99.97Current Price $99.97
(31% off)31% off.
$145.00Comparable value $145.00
(120)
'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)
Upton Chukka (Men)
Johnston & Murphy

Upton Chukka (Men)

$129.97Current Price $129.97
(27% off)27% off.
$179.00Comparable value $179.00
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)
Esmond Chukka Boot (Men)
Dockers®

Esmond Chukka Boot (Men)

$59.97Current Price $59.97
(36% off)36% off.
$95.00Comparable value $95.00
(5)
Speed Strike 2 Hiking Boot (Men)
New
Merrell

Speed Strike 2 Hiking Boot (Men)

$89.97Current Price $89.97
(25% off)25% off.
$120.00Comparable value $120.00
(17)
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
(3)
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
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)
Azzano Plain Toe Chelsea Boot (Men)
Florsheim

Azzano Plain Toe Chelsea 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
Neumal Crafted Regenerate Water Resistant Chukka Boot (Men)
UGG®

Neumal Crafted Regenerate Water Resistant Chukka Boot (Men)

$74.96Current Price $74.96
(62% off)62% off.
$200.00Comparable value $200.00
(4)
Only a few left
Enrico Chelsea Boot (Men)
Aquatalia

Enrico Chelsea Boot (Men)

$229.97Current Price $229.97
(58% off)58% off.
$550.00Comparable value $550.00
'Seneca' Moc Toe Boot (Men)
Eastland

'Seneca' Moc Toe Boot (Men)

$44.97Current Price $44.97
(Extra 40% off)Includes extra 40% off.
$74.96Previous Price $74.96
$125.00Comparable value $125.00
Price Drop
Grand Chelsea Boot (Men)
Cole Haan

Grand Chelsea Boot (Men)

$32.98Current Price $32.98
(Extra 40% off)Includes extra 40% off.
$54.98Previous Price $54.98
$150.00Comparable value $150.00
Price Drop
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
(19)
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
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
(1)
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
(73)
'Seneca' Moc Toe Boot (Men)
Eastland

'Seneca' Moc Toe Boot (Men)

$44.97Current Price $44.97
(Extra 40% off)Includes extra 40% off.
$74.96Previous Price $74.96
$125.00Comparable value $125.00
Price Drop
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
(6)
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
(391)
Hybrid Low Boy Chelsea Boot (Men)
Ariat

Hybrid Low Boy Chelsea Boot (Men)

$89.97Current Price $89.97
(43% off)43% off.
$159.95Comparable value $159.95
(27)
Britton Road Mid Gore-Tex® Waterproof Boot (Men)
Timberland

Britton Road Mid Gore-Tex® Waterproof Boot (Men)

$58.48Current Price $58.48
(Extra 40% off)Includes extra 40% off.
$97.48Previous Price $97.48
$260.00Comparable value $260.00
Price Drop
Only a few left
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
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)
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
Sting Western Boot (Men)
Ariat

Sting Western Boot (Men)

$139.97Current Price $139.97
(50% off)50% off.
$279.95Comparable value $279.95
(76)
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
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)
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)
Grand Lug Boot (Men)
New
Cole Haan

Grand Lug Boot (Men)

$89.97Current Price $89.97
(43% off)43% off.
$160.00Comparable value $160.00
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)
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)
Chalet Leather Cap Toe Boot (Men)
Florsheim

Chalet Leather Cap Toe Boot (Men)

$109.97Current Price $109.97
(29% off)29% off.
$155.00Comparable value $155.00
(21)
Seth Memory Foam Chukka Boot (Men)
Eastland

Seth Memory Foam Chukka Boot (Men)

$26.97Current Price $26.97
(Extra 40% off)Includes extra 40% off.
$44.96Previous Price $44.96
$90.00Comparable value $90.00
Price Drop
(1)
'Mesteno' Boot (Men)
Ariat

'Mesteno' Boot (Men)

$149.97Current Price $149.97
(44% off)44% off.
$269.95Comparable value $269.95
(49)
Only a few left
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)
'Daily Double' Chelsea Boot (Men)
Eastland

'Daily Double' Chelsea Boot (Men)

$44.97Current Price $44.97
(Extra 40% off)Includes extra 40% off.
$74.96Previous Price $74.96
$125.00Comparable value $125.00
Price Drop
(8)
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)
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
(12)
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)
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)
Futurity Royal Western Boot (Men)
New
Ariat

Futurity Royal Western Boot (Men)

$179.97Current Price $179.97
(40% off)40% off.
$299.95Comparable value $299.95
(2)
Moc Toe Boot (Men)
Dockers®

Moc Toe Boot (Men)

$64.97Current Price $64.97
(31% off)31% off.
$95.00Comparable value $95.00
(4)
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)
Truman Chelsea Boot (Men)
Dockers®

Truman Chelsea Boot (Men)

$59.97Current Price $59.97
(36% off)36% off.
$95.00Comparable value $95.00
(5)
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)
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
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)
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