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Comfort Boots for Men

  • All Comfort
  • Boots
  • Dress Shoes
  • Loafers & Oxfords
  • Sneakers
145 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
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)
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)
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)
Otto Chukka Boot - Wide Width Available (Men)
NUNN BUSH

Otto Chukka Boot - Wide Width Available (Men)

$20.23 – $79.97Current Price $20.23 to $79.97
(Extra 40% off select items)Includes extra 40% off select items.
$33.72Previous Price $33.72
$95.00 – $110.00Comparable value $95.00 to $110.00
Price Drop
(14)
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)
Upton Chukka (Men)
New
Johnston & Murphy

Upton Chukka (Men)

$129.97Current Price $129.97
(27% off)27% off.
$179.00Comparable value $179.00
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
(3)
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
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
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)
Newmark Grand Water Resistant Chelsea Boot (Men)
Cole Haan

Newmark Grand Water Resistant 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
(7)
Only a few left
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)
Burleigh Chukka (Men)
UGG®

Burleigh Chukka (Men)

$89.97Current Price $89.97
(43% off)43% off.
$160.00Comparable value $160.00
(20)
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)
Chalet Chelsea Boot (Men)
Florsheim

Chalet Chelsea Boot (Men)

$99.97Current Price $99.97
(31% off)31% off.
$145.00Comparable value $145.00
(119)
Upton Chelsea Boot (Men)
New
Johnston & Murphy

Upton Chelsea Boot (Men)

$129.97Current Price $129.97
(27% off)27% off.
$179.00Comparable value $179.00
(7)
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)
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)
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)
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
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)
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
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)
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)
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
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
Killington Trekker Mid Boot (Men)
Timberland

Killington Trekker Mid Boot (Men)

$69.97Current Price $69.97
(50% off)50% off.
$140.00Comparable value $140.00
(1)
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
(3)
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
Burleigh Chelsea Boot (Men)
UGG®

Burleigh Chelsea Boot (Men)

$99.97Current Price $99.97
(44% off)44% off.
$180.00Comparable value $180.00
(12)
Only a few left
x John Deere Relaxed Fit Terraform Waterproof Boot (Men)
SKECHERS

x John Deere Relaxed Fit Terraform Waterproof Boot (Men)

$59.97Current Price $59.97
(55% off)55% off.
$135.00Comparable value $135.00
(9)
Only a few left
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
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)
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)
Edwin Weatherproof Lace-Up Boot (Men)
Aquatalia

Edwin Weatherproof Lace-Up Boot (Men)

$89.99 – $93.58Current Price $89.99 to $93.58
(Extra 40% off)Includes extra 40% off.
$149.99 – $155.98Previous Price $149.99 to $155.98
$575.00Comparable value $575.00
Price Drop
Only a few left
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)
Delton Plain Toe Chelsea Boot (Men)
NUNN BUSH

Delton Plain Toe Chelsea Boot (Men)

$24.73 – $54.97Current Price $24.73 to $54.97
(Extra 40% off select items)Includes extra 40% off select items.
$41.22Previous Price $41.22
$95.00Comparable value $95.00
Price Drop
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)
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)
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
(7)
Lockhart Mini Lug Suede Chelsea Boot (Men)
New
Nordstrom

Lockhart Mini Lug Suede Chelsea Boot (Men)

$49.97Current Price $49.97
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)
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)
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
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
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)
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
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 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
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
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
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)
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)
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)
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
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
(16)
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)
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
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)
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
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)
Chase Plain Toe Chukka Boot - Wide Width Available (Men)
NUNN BUSH

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

$20.23 – $54.97Current Price $20.23 to $54.97
(Extra 40% off select items)Includes extra 40% off select items.
$33.72 – $41.22Previous Price $33.72 to $41.22
$90.00 – $95.00Comparable value $90.00 to $95.00
Price Drop
(13)
Forge Lace-Up Boot (Men)
Florsheim

Forge Lace-Up Boot (Men)

$49.48Current Price $49.48
(Extra 40% off)Includes extra 40% off.
$82.47Previous Price $82.47
$135.00Comparable value $135.00
Price Drop
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)
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.
$168.98 – $194.96Previous Price $168.98 to $194.96
$625.00Comparable value $625.00
Price Drop
Forge Chelsea Boot (Men)
Florsheim

Forge Chelsea Boot (Men)

$42.88 – $49.48Current Price $42.88 to $49.48
(Extra 40% off)Includes extra 40% off.
$71.48 – $82.47Previous Price $71.48 to $82.47
$130.00Comparable value $130.00
Price Drop
(3)
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)
Enrico Chelsea Boot (Men)
Aquatalia

Enrico Chelsea Boot (Men)

$229.97Current Price $229.97
(58% off)58% off.
$550.00Comparable value $550.00
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
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