BørnTheo Chukka Boot (Men)$59.97 – $79.97Current Price $59.97 to $79.97(Up to 53% off select items)Up to 53% off select items.$130.00Comparable value $130.00(6)
Johnston & MurphyBoswell Chukka Boot (Men)$89.97Current Price $89.97(48% off)48% off.$175.00Comparable value $175.00(10)
BørnLincoln Chukka (Men)$89.97Current Price $89.97(41% off)41% off.$155.00Comparable value $155.00(4)
Cole Haan2.Zerogrand Chukka Boot (Men)$99.97Current Price $99.97(70% off)70% off.$338.00Comparable value $338.00(397)
Johnston & MurphyUpton Chukka Boot (Men)$69.97Current Price $69.97(58% off)58% off.$169.00Comparable value $169.00(18)
New!TimberlandPremium Waterproof Lace-Up Chukka Boot (Men)$59.97Current Price $59.97(60% off)60% off.$150.00Comparable value $150.00(41)
Cole HaanGrand Atlantic Chukka Boot - Wide Width Available (Men)$74.97 – $99.97Current Price $74.97 to $99.97(Up to 62% off select items)Up to 62% off select items.$200.00Comparable value $200.00(38)
Cole HaanChamberlin Grand Water Resistant Chelsea Boot (Men)$129.97Current Price $129.97(50% off)50% off.$260.00Comparable value $260.00(6)
New!Johnston & MurphyBorland Chelsea Boot (Men)$79.97Current Price $79.97(50% off)50% off.$160.00Comparable value $160.00(1)
FlorsheimChalet Chelsea Boot (Men)$99.97Current Price $99.97(31% off)31% off.$145.00Comparable value $145.00(111)
NUNN BUSHChase Plain Toe Chukka Boot - Wide Width Available (Men)$44.97 – $54.97Current Price $44.97 to $54.97(Up to 52% off)Up to 52% off.$90.00 – $95.00Comparable value $90.00 to $95.00(13)
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(1)
Johnston & MurphyCalder Chukka Boot (Men)$79.97Current Price $79.97(51% off)51% off.$165.00Comparable value $165.00(21)
FlorsheimForge Lace-Up Boot (Men)$109.97Current Price $109.97(18% off)18% off.$135.00Comparable value $135.00
NordstromPayton Mini Lug Pebbled Leather Chukka Boot (Men)$69.97Current Price $69.97(46% off)46% off.$129.95Comparable value $129.95(12)Only a few left
MerrellMoab 3 Vista Waterproof Mid Hiking Shoe (Men)$69.97Current Price $69.97(53% off)53% off.$150.00Comparable value $150.00(42)
New!SperryColdbay Waterproof 3-Eye Duck Shoe (Men)$49.97Current Price $49.97(61% off)61% off.$130.00Comparable value $130.00
Clear The RackCole HaanGrand Chelsea Boot (Men)$41.23Current Price $41.23(Extra 25% off)Includes extra 25% off.$54.98Previous Price $54.98$150.00Comparable value $150.00
Clarks®Wallaston Chukka Boot (Men)$79.97Current Price $79.97(33% off)33% off.$120.00Comparable value $120.00(1)
New!Cole HaanMorse GRANDFØAM Chukka Boot (Men)$129.97Current Price $129.97(40% off)40% off.$220.00Comparable value $220.00
New!Clarks®Wallaston Low Chukka Boot (Men)$84.97Current Price $84.97(22% off)22% off.$110.00Comparable value $110.00
Cole HaanChamberlin Grand Chukka Boot (Men)$97.47 – $129.97Current Price $97.47 to $129.97(Up to 66% off select items)Up to 66% off select items.$290.00Comparable value $290.00(1)
EastlandHugo Boot$44.97 – $59.97Current Price $44.97 to $59.97(Up to 55% off select items)Up to 55% off select items.$100.00Comparable value $100.00
FlorsheimChalet Leather Cap Toe Boot (Men)$109.97Current Price $109.97(29% off)29% off.$155.00Comparable value $155.00(16)
New!TimberlandKillington Trekker Mid Boot (Men)$69.97Current Price $69.97(50% off)50% off.$140.00Comparable value $140.00
Johnston & MurphyLewis Side Zip Boot (Men)$69.97Current Price $69.97(45% off)45% off.$129.00Comparable value $129.00(39)
NUNN BUSHOtto Chukka Boot - Wide Width Available (Men)$44.97 – $79.97Current Price $44.97 to $79.97(Up to 52% off)Up to 52% off.$95.00 – $110.00Comparable value $95.00 to $110.00(13)
Cole HaanGrand Atlantic Chelsea Boot (Men)$74.97 – $99.97Current Price $74.97 to $99.97(Up to 62% off select items)Up to 62% off select items.$200.00Comparable value $200.00(2)
EastlandHigh Fidelity Leather Boot (Men)$79.97 – $119.97Current Price $79.97 to $119.97(Up to 40% off)Up to 40% off.$135.00Comparable value $135.00(1)
Clarks®Steadwell Plain Toe Chukka Boot (Men)$79.97Current Price $79.97(27% off)27% off.$110.00Comparable value $110.00
New!TimberlandAttleboro Chelsea Boot (Men)$69.97Current Price $69.97(Up to 50% off)Up to 50% off.$130.00 – $140.00Comparable value $130.00 to $140.00(7)
FlorsheimForge Chelsea Boot (Men)$109.97Current Price $109.97(15% off)15% off.$130.00Comparable value $130.00(1)
EastlandJack Chukka Boot (Men)$89.97Current Price $89.97(28% off)28% off.$125.00Comparable value $125.00(1)
NUNN BUSHOdell II Wingtip Boot (Men)$89.97Current Price $89.97(18% off)18% off.$110.00Comparable value $110.00(2)
FlorsheimRuvo Chelsea Boot (Men)$109.97Current Price $109.97(26% off)26% off.$150.00Comparable value $150.00(21)
UGG®Classic Mini Boot (Men)$89.97Current Price $89.97(43% off)43% off.$160.00Comparable value $160.00(10)Only a few left
BørnSeth Chukka Boot (Men)$89.97Current Price $89.97(35% off)35% off.$140.00Comparable value $140.00(7)
UGG®Emmett Waterproof Snow Boot (Men)$79.97Current Price $79.97(46% off)46% off.$150.00Comparable value $150.00(123)Only a few left
Cole HaanGrand Lug Sole Boot (Men)$99.97Current Price $99.97(25% off)25% off.$135.00Comparable value $135.00(2)
UGG®Burleigh Chukka (Men)$89.97Current Price $89.97(43% off)43% off.$160.00Comparable value $160.00(17)Only a few left
New!TimberlandEuro Spring Mid Hiking Boot (Men)$69.97Current Price $69.97(46% off)46% off.$130.00Comparable value $130.00
AriatHeritage Western Boot (Men)$112.47Current Price $112.47(40% off)40% off.$189.95Comparable value $189.95(347)
AriatSport Stratten Leather Boot (Men)$99.97Current Price $99.97(47% off)47% off.$189.95Comparable value $189.95(51)Only a few left
TimberlandAttleboro Mid Lace-Up Boot (Men)$74.97Current Price $74.97(46% off)46% off.$140.00Comparable value $140.00(8)Only a few left
TimberlandAttleboro Mid Chukka Boot (Men)$69.97Current Price $69.97(46% off)46% off.$130.00Comparable value $130.00(5)
Dockers®Esmond Chukka Boot (Men)$59.97Current Price $59.97(36% off)36% off.$95.00Comparable value $95.00
New!SperryClifton Waterproof Chelsea Duck Boot (Men)$49.97Current Price $49.97(54% off)54% off.$110.00Comparable value $110.00
EastlandSeth Memory Foam Chukka Boot (Men)$44.97Current Price $44.97(50% off)50% off.$90.00Comparable value $90.00(1)
UGG®Neumel Chukka Boot (Men)$109.97Current Price $109.97(26% off)26% off.$150.00Comparable value $150.00(459)Only a few left
Cole HaanNewmark Grand Water Resistant Chelsea Boot (Men)$129.97Current Price $129.97(63% off)63% off.$360.00Comparable value $360.00(7)
FlorsheimAzzano Plain Toe Chukka Boot (Men)$109.97Current Price $109.97(24% off)24% off.$145.00Comparable value $145.00
Cole HaanGrand 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(14)
BørnEli Suede Chukka Boot (Men)$89.97Current Price $89.97(30% off)30% off.$130.00Comparable value $130.00(2)
SKECHERSx John Deere Relaxed Fit Terraform Waterproof Boot (Men)$59.97Current Price $59.97(55% off)55% off.$135.00Comparable value $135.00(9)
Clarks®Weltridge Side Zip Boot (Men)$94.97Current Price $94.97(26% off)26% off.$130.00Comparable value $130.00(2)
NUNN BUSHDelton Plain Toe Chelsea Boot (Men)$54.97Current Price $54.97(42% off)42% off.$95.00Comparable value $95.00
AriatWillie French Toe Western Boot (Men)$149.97Current Price $149.97(40% off)40% off.$249.95Comparable value $249.95(6)Only a few left
Clarks®Maplewalk Moc Toe Boot (Men)$79.97Current Price $79.97(33% off)33% off.$120.00Comparable value $120.00(6)
SperryAvenue Duck Boot (Men)$59.97Current Price $59.97(50% off)50% off.$120.00Comparable value $120.00(16)
MerrellMoab 3 Mid Waterproof Hiking Shoe (Men)$99.97Current Price $99.97(41% off)41% off.$170.00Comparable value $170.00(364)
EastlandEthan 1955 Cap Toe Boot (Men)$99.99Current Price $99.99(55% off)55% off.$225.00Comparable value $225.00
TimberlandBritton Road Mid Gore-Tex® Waterproof Boot (Men)$149.97Current Price $149.97(42% off)42% off.$260.00Comparable value $260.00
Clarks®Walpath Waterproof Chukka Boot (Men)$99.97Current Price $99.97(23% off)23% off.$130.00Comparable value $130.00(1)
Dockers®Thomas Lace-Up Boot (Men)$59.97Current Price $59.97(36% off)36% off.$95.00Comparable value $95.00
Dockers®Dee Chukka Boot (Men)$39.97Current Price $39.97(57% off)57% off.$95.00Comparable value $95.00
EastlandPatterson Cap Toe Chukka Boot (Men)$44.97Current Price $44.97(50% off)50% off.$90.00Comparable value $90.00
BørnThomson Chukka Boot (Men)$89.97Current Price $89.97(30% off)30% off.$130.00Comparable value $130.00(25)
Dockers®Esmond Plain Toe Chukka Boot (Men)$69.97Current Price $69.97(17% off)17% off.$85.00Comparable value $85.00(5)
Clarks®Shepton Easy Chelsea Boot (Men)$94.97Current Price $94.97(26% off)26% off.$130.00Comparable value $130.00
NUNN BUSHOtis II Chelsea Boot (Men)$89.97Current Price $89.97(18% off)18% off.$110.00Comparable value $110.00(1)
Cole HaanNewmark Grand Chelsea Boot (Men)$129.97Current Price $129.97(63% off)63% off.$360.00Comparable value $360.00