New MarkdownCole Haan2.Zerogrand Chukka Boot (Men)$74.96 – $99.97Current Price $74.96 to $99.97(Up to 77% off select items)Up to 77% off select items.$338.00Comparable value $338.00(398)
New MarkdownBørnTheo Chukka Boot (Men)$55.96 – $59.96Current Price $55.96 to $59.96(Up to 56% off)Up to 56% off.$130.00Comparable value $130.00(7)
New MarkdownAlesburyRodale Boot (Men)$24.99 – $27.96Current Price $24.99 to $27.96(Up to 70% off)Up to 70% off.$85.00Comparable value $85.00
New MarkdownFlorsheimForge Lace-Up Boot (Men)$82.47Current Price $82.47(38% off)38% off.$135.00Comparable value $135.00
New MarkdownMarc Joseph New YorkClark Road Hands-Free Slip-On Derby (Men)$59.96Current Price $59.96(63% off)63% off.$165.00Comparable value $165.00(2)
New MarkdownSperryTop-Sider Saltwater Quilted Shaft Duck Boot (Men)$34.96Current Price $34.96(70% off)70% off.$120.00Comparable value $120.00(69)
New MarkdownCole HaanGrand Atlantic Chukka Boot - Wide Width Available (Men)$74.96Current Price $74.96(62% off)62% off.$200.00Comparable value $200.00(38)
New MarkdownAllen EdmondsDonovan Chukka Boot (Men)$129.98 – $199.97Current Price $129.98 to $199.97(Up to 73% off select items)Up to 73% off select items.$495.00Comparable value $495.00
New MarkdownBørnThomson Chukka Boot (Men)$62.96Current Price $62.96(51% off)51% off.$130.00Comparable value $130.00(25)
New MarkdownRESERVE FOOTWEARGerard Lug Sole Boot (Men)$42.23 – $48.72Current Price $42.23 to $48.72(Up to 66% off)Up to 66% off.$125.00Comparable value $125.00(4)
New MarkdownFlorsheimForge Chelsea Boot (Men)$71.48 – $82.47Current Price $71.48 to $82.47(Up to 45% off)Up to 45% off.$130.00Comparable value $130.00(1)
New MarkdownNUNN BUSHChase Plain Toe Chukka Boot - Wide Width Available (Men)$32.48 – $54.97Current Price $32.48 to $54.97(Up to 65% off select items)Up to 65% off select items.$90.00 – $95.00Comparable value $90.00 to $95.00(13)
New MarkdownMarc Joseph New YorkHudson Yards 2.0 Pull-On Boot (Men)$55.96 – $59.96Current Price $55.96 to $59.96(Up to 71% off)Up to 71% off.$195.00Comparable value $195.00(3)
New MarkdownEastlandHugo Boot$44.96 – $44.97Current Price $44.96 to $44.97(55% off)55% off.$100.00Comparable value $100.00
New MarkdownSteve MaddenLisbon Buckle Boot (Men)$49.99 – $79.97Current Price $49.99 to $79.97(Up to 68% off select items)Up to 68% off select items.$160.00Comparable value $160.00(1)
New MarkdownVINTAGE FOUNDRYLyle Chelsea Boot (Men)$69.98 – $74.96Current Price $69.98 to $74.96(Up to 65% off)Up to 65% off.$200.00Comparable value $200.00(2)
New MarkdownFryeBowery Lace-Up Boot (Men)$129.98 – $199.97Current Price $129.98 to $199.97(Up to 65% off select items)Up to 65% off select items.$378.00Comparable value $378.00(50)
New MarkdownBørnLincoln Chukka (Men)$67.47Current Price $67.47(56% off)56% off.$155.00Comparable value $155.00(4)
New MarkdownBruno MagliJoca Lug Sole Boot (Men)$113.98Current Price $113.98(74% off)74% off.$450.00Comparable value $450.00(2)
New MarkdownBørnEli Suede Chukka Boot (Men)$67.47 – $89.97Current Price $67.47 to $89.97(Up to 48% off select items)Up to 48% off select items.$130.00Comparable value $130.00(3)
New MarkdownEastlandAllagash Standard Derby Boot (Men)$54.98 – $69.96Current Price $54.98 to $69.96(Up to 62% off)Up to 62% off.$145.00Comparable value $145.00
New MarkdownEastlandBaxter Boot (Men)$48.96 – $49.99Current Price $48.96 to $49.99(Up to 63% off)Up to 63% off.$135.00Comparable value $135.00
New MarkdownFryeDylan Cap Toe Boot (Men)$132.96Current Price $132.96(61% off)61% off.$348.00Comparable value $348.00(13)
New MarkdownHawker RyeFrausen Lace-Up Boot (Men)$27.96Current Price $27.96(68% off)68% off.$89.00Comparable value $89.00
New MarkdownFryeDylan Cap Toe Boot (Men)$142.98Current Price $142.98(68% off)68% off.$458.00Comparable value $458.00(5)
New MarkdownJohnston & MurphyLewis Chelsea Boot (Men)$49.99Current Price $49.99(61% off)61% off.$129.00Comparable value $129.00(5)
New MarkdownKARL LAGERFELD PARISDouble Buckle Suede Engineer Boot (Men)$49.99 – $59.96Current Price $49.99 to $59.96(Up to 80% off)Up to 80% off.$250.00Comparable value $250.00(33)
New MarkdownAllen EdmondsHiggins Mill Lug Zip Boot (Men)$194.98 – $199.97Current Price $194.98 to $199.97(Up to 60% off select items)Up to 60% off select items.$495.00Comparable value $495.00(76)
New MarkdownJohnston & MurphyJenson Chelsea Boot (Men)$136.48Current Price $136.48(58% off)58% off.$328.00Comparable value $328.00(3)
New MarkdownVANCE COStratton Chukka Boot (Men)$56.22 – $74.97Current Price $56.22 to $74.97(Up to 48% off select items)Up to 48% off select items.$109.99Comparable value $109.99
New MarkdownClarks®Maplewalk Rise Boot (Men)$67.47 – $89.97Current Price $67.47 to $89.97(Up to 43% off select items)Up to 43% off select items.$120.00Comparable value $120.00
New Markdownrag & boneTucker Moc Toe Boot (Men)$123.48 – $149.96Current Price $123.48 to $149.96(Up to 74% off)Up to 74% off.$478.00Comparable value $478.00(1)
New MarkdownClarks®Walpath Waterproof Chelsea Boot (Men)$74.96Current Price $74.96(42% off)42% off.$130.00Comparable value $130.00Only a few left
New MarkdownEastlandChimney Pond Chelsea Boot (Men)$69.96 – $74.96Current Price $69.96 to $74.96(Up to 51% off)Up to 51% off.$145.00Comparable value $145.00
New MarkdownSteve MaddenWesley Chelsea Boot (Men)$55.23 – $63.72Current Price $55.23 to $63.72(Up to 63% off)Up to 63% off.$150.00Comparable value $150.00(1)
New MarkdownDEARFOAMSShepparton Genuine Shearling Boot (Men)$49.99Current Price $49.99(61% off)61% off.$130.00Comparable value $130.00(12)
New MarkdownEastlandBelgrade Boot (Men)$49.99 – $74.97Current Price $49.99 to $74.97(Up to 64% off select items)Up to 64% off select items.$140.00Comparable value $140.00
New MarkdownFlorsheimAzzano Plain Toe Chelsea Boot (Men)$82.47Current Price $82.47(43% off)43% off.$145.00Comparable value $145.00
New MarkdownMagnanniBetun Boot (Men)$187.47 – $249.97Current Price $187.47 to $249.97(Up to 58% off select items)Up to 58% off select items.$450.00Comparable value $450.00(20)
New MarkdownFryeDylan Cap Toe Boot (Men)$113.98Current Price $113.98(67% off)67% off.$348.00Comparable value $348.00(10)
New MarkdownJohnston & MurphyLewis Side Zip Boot (Men)$49.99Current Price $49.99(61% off)61% off.$129.00Comparable value $129.00(40)
New MarkdownReaction Kenneth ColeCombat Boot (Men)$52.47Current Price $52.47(62% off)62% off.$140.00Comparable value $140.00(1)Only a few left
New MarkdownAquataliaEdmundo Water Repellent Combat Boot (Men)$194.96Current Price $194.96(68% off)68% off.$625.00Comparable value $625.00(4)
Maison ForteCitadel Leather Boot (Men)$82.47Current Price $82.47(61% off)61% off.$215.00Comparable value $215.00(17)Only a few left
New MarkdownDEARFOAMSWarm Up Faux Shearling Bootie (Men)$12.98 – $14.96Current Price $12.98 to $14.96(Up to 74% off)Up to 74% off.$50.00Comparable value $50.00(14)
New MarkdownDockers®Townsend Chelsea Boot (Men)$29.96Current Price $29.96(68% off)68% off.$95.00Comparable value $95.00(1)
New MarkdownEastlandCryus Chelsea Boot (Men)$44.96 – $44.97Current Price $44.96 to $44.97(50% off)50% off.$90.00Comparable value $90.00(11)
New MarkdownAquataliaGustavo Zip Combat Boot (Men)$168.98 – $259.97Current Price $168.98 to $259.97(Up to 72% off select items)Up to 72% off select items.$625.00Comparable value $625.00
EastlandFinn Plain Toe Boot (Men)$44.96Current Price $44.96(50% off)50% off.$90.00Comparable value $90.00(2)
New MarkdownFryeBowery Chukka Boot (Men)$99.99 – $123.50Current Price $99.99 to $123.50(Up to 71% off)Up to 71% off.$348.00Comparable value $348.00(50)
New MarkdownRESERVE FOOTWEAREmmett Cap Toe Boot (Men)$37.47Current Price $37.47(61% off)61% off.$98.00Comparable value $98.00(6)
New MarkdownBOSSFoster Boot (Men)$112.47Current Price $112.47(62% off)62% off.$299.00Comparable value $299.00
New MarkdownBarbourDeckham Plain Toe Boot (Men)$71.98 – $90.96Current Price $71.98 to $90.96(Up to 70% off)Up to 70% off.$240.00Comparable value $240.00(2)
New MarkdownALDOKnighton Boot (Men)$38.98 – $49.99Current Price $38.98 to $49.99(Up to 70% off)Up to 70% off.$130.00 – $150.00Comparable value $130.00 to $150.00
New MarkdownStuart WeitzmanAugustine Boot (Men)$316.23 – $402.47Current Price $316.23 to $402.47(Up to 71% off)Up to 71% off.$1,100.00Comparable value $1,100.00
EastlandSeth Memory Foam Chukka Boot (Men)$44.96Current Price $44.96(50% off)50% off.$90.00Comparable value $90.00(1)
New MarkdownBOSSPlain Toe Lug Sole Boot (Men)$94.47Current Price $94.47(65% off)65% off.$270.00Comparable value $270.00(1)
EastlandPatterson Cap Toe Chukka Boot (Men)$44.96Current Price $44.96(50% off)50% off.$90.00Comparable value $90.00
New MarkdownTAFTLeather Boot (Men)$71.48Current Price $71.48(62% off)62% off.$189.99Comparable value $189.99(28)Only a few left
New MarkdownAQUATHERM BY SANTANA CANADASkyline Boot (Men)$49.48Current Price $49.48(64% off)64% off.$139.99Comparable value $139.99Only a few left
New MarkdownVANCE COSlater Chelsea Boot (Men)$44.98 – $56.22Current Price $44.98 to $56.22(Up to 59% off)Up to 59% off.$109.99Comparable value $109.99(1)Only a few left
New MarkdownReaction Kenneth ColeLug Sole Boot (Men)$48.72Current Price $48.72(62% off)62% off.$129.00Comparable value $129.00Only a few left
Eastland'Daily Double' Chelsea Boot (Men)$74.96Current Price $74.96(40% off)40% off.$125.00Comparable value $125.00(8)
New MarkdownPalladiumPampa Travel Lite Waterproof Boot (Unisex)$48.96 – $69.97Current Price $48.96 to $69.97(Up to 69% off select items)Up to 69% off select items.$160.00Comparable value $160.00(1)
New MarkdownDingoThe Duke Lizard Embossed Cowboy Boot (Men)$74.96Current Price $74.96(42% off)42% off.$129.99Comparable value $129.99
New MarkdownPalladium'Baggy' Canvas Boot$22.99 – $32.97Current Price $22.99 to $32.97(Up to 67% off select items)Up to 67% off select items.$69.95Comparable value $69.95(14)Only a few left
New MarkdownEastlandHerman Water Resistant Chelsea Boot (Men)$59.96 – $79.97Current Price $59.96 to $79.97(Up to 55% off select items)Up to 55% off select items.$135.00Comparable value $135.00(2)
New MarkdownXRAYLazlo Boot (Men)$24.47 – $24.99Current Price $24.47 to $24.99(Up to 62% off)Up to 62% off.$65.00Comparable value $65.00(4)
New MarkdownSORELCaribou Royal Waterproof Boot (Men)$89.96Current Price $89.96(60% off)60% off.$225.00Comparable value $225.00