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Comfort Boots for Men

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

Chalet Chelsea Boot (Men)

$99.97Current Price $99.97
(31% off)31% off.
$145.00Comparable value $145.00
(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
Grand Atlantic Chelsea Boot (Men)
Clear The Rack
Cole Haan

Grand Atlantic Chelsea Boot (Men)

$33.72 – $56.22Current Price $33.72 to $56.22
(Extra 25% off)Includes extra 25% off.
$44.97 – $74.96Previous Price $44.97 to $74.96
$200.00Comparable value $200.00
(8)
Boswell Chukka Boot (Men)
Clear The Rack
Johnston & Murphy

Boswell Chukka Boot (Men)

$43.86 – $50.60Current Price $43.86 to $50.60
(Extra 25% off)Includes extra 25% off.
$58.48 – $67.47Previous Price $58.48 to $67.47
$175.00Comparable value $175.00
(15)
Grand Atlantic Chukka Boot - Wide Width Available (Men)
Clear The Rack
Cole Haan

Grand Atlantic Chukka Boot - Wide Width Available (Men)

$33.72Current Price $33.72
(Extra 25% off)Includes extra 25% off.
$44.97Previous Price $44.97
$200.00Comparable value $200.00
(43)
Chamberlin Grand Chukka Boot (Men)
Clear The Rack
Cole Haan

Chamberlin Grand Chukka Boot (Men)

$73.10Current Price $73.10
(Extra 25% off)Includes extra 25% off.
$97.47Previous Price $97.47
$290.00Comparable value $290.00
(10)
Truman Chelsea Boot (Men)
Dockers®

Truman Chelsea Boot (Men)

$59.97Current Price $59.97
(36% off)36% off.
$95.00Comparable value $95.00
(5)
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
'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)
Downtown Western Boot (Men)
Ariat

Downtown Western Boot (Men)

$129.97Current Price $129.97
(50% off)50% off.
$259.95Comparable value $259.95
(25)
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
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
Otto Chukka Boot - Wide Width Available (Men)
Clear The Rack
NUNN BUSH

Otto Chukka Boot - Wide Width Available (Men)

$14.99 – $79.97Current Price $14.99 to $79.97
(Extra 25% off select items)Includes extra 25% off select items.
$19.99Previous Price $19.99
$95.00 – $110.00Comparable value $95.00 to $110.00
(14)
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)
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)
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)
Grand Remix Chukka Boot (Men)
Clear The Rack
Cole Haan

Grand Remix Chukka Boot (Men)

$56.22 – $99.97Current Price $56.22 to $99.97
(Extra 25% off select items)Includes extra 25% off select items.
$74.96Previous Price $74.96
$220.00 – $230.00Comparable value $220.00 to $230.00
(15)
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
Chamberlin Grand Water Resistant Chelsea Boot (Men)
Clear The Rack
Cole Haan

Chamberlin Grand Water Resistant Chelsea Boot (Men)

$73.10 – $119.97Current Price $73.10 to $119.97
(Extra 25% off select items)Includes extra 25% off select items.
$97.47Previous Price $97.47
$260.00Comparable value $260.00
(11)
Chase Plain Toe Chukka Boot - Wide Width Available (Men)
Clear The Rack
NUNN BUSH

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

$14.99 – $54.97Current Price $14.99 to $54.97
(Extra 25% off select items)Includes extra 25% off select items.
$19.99Previous Price $19.99
$95.00Comparable value $95.00
(14)
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
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
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)
Wexford Chelsea Boot (Men)
Ariat

Wexford Chelsea Boot (Men)

$99.97Current Price $99.97
(47% off)47% off.
$189.95Comparable value $189.95
(4)
Chalet Leather Cap Toe Boot (Men)
Clear The Rack
Florsheim

Chalet Leather Cap Toe Boot (Men)

$61.85Current Price $61.85
(Extra 25% off)Includes extra 25% off.
$82.47Previous Price $82.47
$155.00Comparable value $155.00
(22)
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)
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)
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)
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
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)
Speed Strike 2 Hiking Boot (Men)
New
Merrell

Speed Strike 2 Hiking Boot (Men)

$84.97 – $89.97Current Price $84.97 to $89.97
(Up to 25% off)Up to 25% off.
$110.00 – $120.00Comparable value $110.00 to $120.00
(20)
Bend Chelsea Boot (Men)
New
Birkenstock

Bend Chelsea Boot (Men)

$99.97Current Price $99.97
(41% off)41% off.
$170.00Comparable value $170.00
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)
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
(4)
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
Hustler Narrow Cutter Toe Cowboy Boot (Men)
New
Ariat

Hustler Narrow Cutter Toe Cowboy Boot (Men)

$119.97Current Price $119.97
(52% off)52% off.
$249.95Comparable value $249.95
(17)
Tempo Sol Waterproof Mid Top Hiking Boot (Men)
New
Merrell

Tempo Sol Waterproof Mid Top Hiking Boot (Men)

$59.97Current Price $59.97
(25% off)25% off.
$80.00Comparable value $80.00
Premium 6-Inch Waterproof Boot (Men)
New
Timberland

Premium 6-Inch Waterproof Boot (Men)

$99.97Current Price $99.97
(52% off)52% off.
$210.00Comparable value $210.00
(2724)
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)
Sport Square Toe Western Boot (Men)
Ariat

Sport Square Toe Western Boot (Men)

$99.97Current Price $99.97
(47% off)47% off.
$189.95Comparable value $189.95
(26)
Only a few left
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)
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)
Morse GRANDFØAM Chukka Boot (Men)
Clear The Rack
Cole Haan

Morse GRANDFØAM Chukka Boot (Men)

$63.36 – $73.10Current Price $63.36 to $73.10
(Extra 25% off)Includes extra 25% off.
$84.48 – $97.47Previous Price $84.48 to $97.47
$220.00Comparable value $220.00
(8)
Dylan Chelsea Boot (Men)
Dockers®

Dylan Chelsea Boot (Men)

$59.97Current Price $59.97
(36% off)36% off.
$95.00Comparable value $95.00
(5)
Maverick Western Boot (Men)
New
Ariat

Maverick Western Boot (Men)

$139.97Current Price $139.97
(46% off)46% off.
$259.95Comparable value $259.95
(5)
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)
Sting Western Boot (Men)
Ariat

Sting Western Boot (Men)

$149.97Current Price $149.97
(46% off)46% off.
$279.95Comparable value $279.95
(92)
Emerald Woods Waterproof Super Boot (Men)
New
Timberland

Emerald Woods Waterproof Super Boot (Men)

$119.97Current Price $119.97
(57% off)57% off.
$280.00Comparable value $280.00
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)
Willie Western Boot (Men)
New
Ariat

Willie Western Boot (Men)

$139.97Current Price $139.97
(46% off)46% off.
$259.95Comparable value $259.95
(20)
Esmond Chukka Boot (Men)
Dockers®

Esmond Chukka Boot (Men)

$59.97Current Price $59.97
(36% off)36% off.
$95.00Comparable value $95.00
(5)
'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)
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)
Oakwood Cowboy Boot (Men)
New
Ariat

Oakwood Cowboy Boot (Men)

$139.97Current Price $139.97
(46% off)46% off.
$259.95Comparable value $259.95
(77)
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)
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
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
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)
Bodie Cowboy Boot (Men)
New
Ariat

Bodie Cowboy Boot (Men)

$99.97Current Price $99.97
(44% off)44% off.
$179.95Comparable value $179.95
(16)
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)
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)
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)
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
Kingham Waterproof Boot (Men)
Ariat

Kingham Waterproof Boot (Men)

$99.97Current Price $99.97
(45% off)45% off.
$184.95Comparable value $184.95
(22)
Maplewalk Rise Boot (Men)
Clarks®

Maplewalk Rise Boot (Men)

$89.97Current Price $89.97
(25% off)25% 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
(2)
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
Slingshot Cowboy Boot (Men)
Ariat

Slingshot Cowboy Boot (Men)

$119.97Current Price $119.97
(50% off)50% off.
$239.95Comparable value $239.95
(119)
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
(20)
Enrico Chelsea Boot (Men)
Aquatalia

Enrico Chelsea Boot (Men)

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