Johnston & MurphyBoswell Chukka Boot (Men)$58.48 – $67.47Current Price $58.48 to $67.47(Up to 66% off)Up to 66% off.$175.00Comparable value $175.00New Markdown(14)
BørnTheo Chukka Boot (Men)$35.97 – $55.96Current Price $35.97 to $55.96(Up to 72% off)Up to 72% off.$130.00Comparable value $130.00New Markdown(10)
Cole HaanMorse GRANDFØAM Chukka Boot (Men)$84.48 – $97.47Current Price $84.48 to $97.47(Up to 61% off)Up to 61% off.$220.00Comparable value $220.00New Markdown(6)
Steve MaddenScotch Lug Sole Boot (Men)$49.98 – $59.96Current Price $49.98 to $59.96(Up to 61% off)Up to 61% off.$130.00Comparable value $130.00New Markdown(10)
FlorsheimChalet Leather Cap Toe Boot (Men)$82.47Current Price $82.47(46% off)46% off.$155.00Comparable value $155.00New Markdown(22)
VINTAGE FOUNDRYLyle Chelsea Boot (Men)$39.98 – $44.97Current Price $39.98 to $44.97(Up to 80% off)Up to 80% off.$200.00Comparable value $200.00New Markdown(4)
Johnston & MurphyBorland Chelsea Boot (Men)$55.96 – $59.96Current Price $55.96 to $59.96(Up to 65% off)Up to 65% off.$160.00Comparable value $160.00New Markdown(5)
NUNN BUSHCircuit 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)
Cole HaanChamberlin Grand Water Resistant Chelsea Boot (Men)$97.47 – $119.97Current Price $97.47 to $119.97(Up to 62% off select items)Up to 62% off select items.$260.00Comparable value $260.00(11)
BørnEli Suede Chukka Boot (Men)$40.48 – $58.48Current Price $40.48 to $58.48(Up to 68% off)Up to 68% off.$130.00Comparable value $130.00New Markdown(3)
Cole HaanGrand Remix Chukka Boot (Men)$74.96 – $99.97Current Price $74.96 to $99.97(Up to 67% off select items)Up to 67% off select items.$220.00 – $230.00Comparable value $220.00 to $230.00New Markdown(15)
Cole HaanChamberlin Grand Chukka Boot (Men)$97.47Current Price $97.47(66% off)66% off.$290.00Comparable value $290.00New Markdown(9)
Steve MaddenPeter Boot (Men)$67.47Current Price $67.47(60% off)60% off.$170.00Comparable value $170.00New Markdown(3)
Cole HaanGrand Atlantic Chelsea Boot (Men)$44.97 – $74.96Current Price $44.97 to $74.96(Up to 77% off)Up to 77% off.$200.00Comparable value $200.00New Markdown(7)
VITTORIO RUSSOWade Boot (Men)$97.47Current Price $97.47(56% off)56% off.$225.00Comparable value $225.00New Markdown(1)
MADDENBronnie Combat Boot (Men)$44.96Current Price $44.96(55% off)55% off.$100.00Comparable value $100.00New Markdown(2)
UGG®Burleigh Chukka (Men)$67.47Current Price $67.47(57% off)57% off.$160.00Comparable value $160.00New Markdown(20) Only a few left
Cole HaanGrand Atlantic Chukka Boot - Wide Width Available (Men)$44.97Current Price $44.97(77% off)77% off.$200.00Comparable value $200.00New Markdown(43)
Cole HaanNewmark Grand Chelsea Boot (Men)$97.47Current Price $97.47(72% off)72% off.$360.00Comparable value $360.00(1)
FryeTyler Boot (Men)$97.48 – $139.97Current Price $97.48 to $139.97(Up to 62% off select items)Up to 62% off select items.$258.00Comparable value $258.00(80) Only a few left
MADDENSawyer Chelsea Boot (Men)$32.48 – $49.97Current Price $32.48 to $49.97(Up to 63% off select items)Up to 63% off select items.$90.00Comparable value $90.00New Markdown(13)
Tommy HilfigerGonzal Lace-Up Boot (Men)$38.98 – $44.96Current Price $38.98 to $44.96(Up to 71% off)Up to 71% off.$135.00Comparable value $135.00New Markdown(2)
Clarks®Wallaston Chukka Boot (Men)$59.96 – $79.97Current Price $59.96 to $79.97(Up to 50% off select items)Up to 50% off select items.$120.00Comparable value $120.00New Markdown(3)
Ted Baker LondonRemington Chelsea Boot (Men)$77.98Current Price $77.98(64% off)64% off.$220.00Comparable value $220.00New Markdown(2)
Johnston & MurphyUpton Chukka Boot (Men)$49.99Current Price $49.99(70% off)70% off.$169.00Comparable value $169.00(19)
VANCE COAustin Cap Toe Chukka Boot - Wide Width (Men)$39.99Current Price $39.99(55% off)55% off.$89.99Comparable value $89.99(3)
Steve MaddenAddis Brogue Boot (Men)$63.72Current Price $63.72(56% off)56% off.$145.00Comparable value $145.00(1)
Tommy HilfigerRoklan Chelsea Boot (Men)$44.96Current Price $44.96(65% off)65% off.$129.00Comparable value $129.00New Markdown
Eastland'Lumber Up' Moc Toe Boot (Men)$35.97 – $99.97Current Price $35.97 to $99.97(Up to 73% off select items)Up to 73% off select items.$135.00 – $150.00Comparable value $135.00 to $150.00New Markdown(4)
FlorsheimForge Chelsea Boot (Men)$38.48 – $82.47Current Price $38.48 to $82.47(Up to 70% off)Up to 70% off.$130.00Comparable value $130.00New Markdown(3) Only a few left
Steve MaddenRilyn Chelsea Boot (Men)$59.96Current Price $59.96(62% off)62% off.$160.00Comparable value $160.00New Markdown(16)
Marc Joseph New YorkClark Road Hands-Free Slip-On Derby (Men)$35.97 – $59.96Current Price $35.97 to $59.96(Up to 78% off)Up to 78% off.$165.00Comparable value $165.00New Markdown(3)
ForsakeDavos Waterproof Boot (Men)$56.22Current Price $56.22(62% off)62% off.$150.00Comparable value $150.00New Markdown(1) Only a few left
ALDOKnighton 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(4)
Cole HaanGrand Lug Sole Boot (Men)$64.98Current Price $64.98(51% off)51% off.$135.00Comparable value $135.00(2)
MADDENBrycee Lug Sole Boot (Men)$42.23 – $48.72Current Price $42.23 to $48.72(Up to 57% off)Up to 57% off.$100.00Comparable value $100.00New Markdown(3) Only a few left
SORELMadson II Chore Waterproof Boot (Men)$49.98Current Price $49.98(74% off)74% off.$195.00Comparable value $195.00New Markdown(12)
Marc Joseph New YorkHudson Yards 2.0 Pull-On Boot (Men)$31.98 – $59.96Current Price $31.98 to $59.96(Up to 83% off)Up to 83% off.$195.00Comparable value $195.00New Markdown(5)
Steve MaddenLisbon Buckle Boot (Men)$27.98 – $59.96Current Price $27.98 to $59.96(Up to 82% off)Up to 82% off.$160.00Comparable value $160.00New Markdown(1)
FlorsheimForge Lace-Up Boot (Men)$82.47Current Price $82.47(38% off)38% off.$135.00Comparable value $135.00(1) Only a few left
TimberlandAttleboro Chelsea Boot (Men)$49.99Current Price $49.99(Up to 64% off)Up to 64% off.$130.00 – $140.00Comparable value $130.00 to $140.00(9)
EastlandBelgrade Boot (Men)$48.73Current Price $48.73(65% off)65% off.$140.00Comparable value $140.00(1) Only a few left
AquataliaEdmundo Water Repellent Combat Boot (Men)$116.97Current Price $116.97(81% off)81% off.$625.00Comparable value $625.00New Markdown(7) Only a few left
Steve MaddenFenton Lug Sole Chelsea Boot (Men)$49.99 – $59.96Current Price $49.99 to $59.96(Up to 61% off)Up to 61% off.$130.00Comparable value $130.00New Markdown(6)
AquataliaGitano Genuine Shearling Lined Water Repellent Boot (Men)$142.98 – $194.96Current Price $142.98 to $194.96(Up to 77% off)Up to 77% off.$625.00Comparable value $625.00New Markdown(1)
Eastland'Seneca' Moc Toe Boot (Men)$39.98Current Price $39.98(68% off)68% off.$125.00Comparable value $125.00New Markdown Only a few left
FlorsheimRuvo Chelsea Boot (Men)$82.47Current Price $82.47(45% off)45% off.$150.00Comparable value $150.00(22) Only a few left
Johnston & MurphyLewis Chelsea Boot (Men)$49.99Current Price $49.99(61% off)61% off.$129.00Comparable value $129.00(7)
FlorsheimAzzano Plain Toe Chelsea Boot (Men)$82.47Current Price $82.47(43% off)43% off.$145.00Comparable value $145.00(2)
Johnston & MurphyBrody Chelsea Boot (Men)$49.99Current Price $49.99(69% off)69% off.$165.00Comparable value $165.00New Markdown(19)
Allen EdmondsDain Combat Boot (Men)$134.96 – $179.97Current Price $134.96 to $179.97(Up to 72% off select items)Up to 72% off select items.$495.00Comparable value $495.00(19)
Allen EdmondsCarson Hybrid Chukka Boot (Men)$97.48 – $149.97Current Price $97.48 to $149.97(Up to 71% off select items)Up to 71% off select items.$345.00Comparable value $345.00(34)
SORELHi-Line Waterproof Lace-Up Boot (Men)$62.96Current Price $62.96(65% off)65% off.$185.00Comparable value $185.00(32)
Steve MaddenRoswel Plain Toe Chelsea Boot (Men)$67.47Current Price $67.47(51% off)51% off.$140.00Comparable value $140.00
Allen EdmondsDonovan Chukka Boot (Men)$129.98Current Price $129.98(73% off)73% off.$495.00Comparable value $495.00New Markdown(3) Only a few left
Allen EdmondsCarter Moc Toe Boot (Men)$129.98Current Price $129.98(73% off)73% off.$495.00Comparable value $495.00(7) Only a few left
Stuart WeitzmanAdwin Chelsea Boot (Men)$324.98Current Price $324.98(66% off)66% off.$975.00Comparable value $975.00(4)
Allen EdmondsChandler Lug Chukka Boot (Men)$129.98 – $149.96Current Price $129.98 to $149.96(Up to 73% off)Up to 73% off.$495.00Comparable value $495.00New Markdown(35) Only a few left
JOHNSTON & MURPHY COLLECTIONWelch Chukka Boot (Men)$76.48Current Price $76.48(71% off)71% off.$265.00Comparable value $265.00New Markdown(9)
EastlandHerman 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(3)
BarbourTucker Chukka Boot (Men)$82.47Current Price $82.47(61% off)61% off.$215.00Comparable value $215.00 Only a few left
Eastland'Daily Double' Chelsea Boot (Men)$39.98 – $44.97Current Price $39.98 to $44.97(Up to 68% off)Up to 68% off.$125.00Comparable value $125.00New Markdown(8)
BOSSCalev Chelsea Boot (Men)$112.47Current Price $112.47(51% off)51% off.$230.00Comparable value $230.00New Markdown
ALDODarionn Waterproof Lace-Up Cap Toe Boot (Men)$58.48Current Price $58.48(66% off)66% off.$175.00Comparable value $175.00(2)
Maison ForteSawyer Hybrid Chukka Boot (Men)$76.96Current Price $76.96(58% off)58% off.$185.00Comparable value $185.00(7) Only a few left
UGG®Classic Minimod Waterproof Wool Boot (Men)$74.96Current Price $74.96(62% off)62% off.$200.00Comparable value $200.00(18) Only a few left
MagnanniKam Chelsea Boot (Men)$199.99Current Price $199.99(59% off)59% off.$495.00Comparable value $495.00New Markdown(2)
NewSORELCyprus™ Waterproof Chelsea Boot (Men)$74.99Current Price $74.99(40% off)40% off.$125.00Previous Price $125.00 Only a few left
TimberlandNewmarket Chukka Boot (Men)$58.48Current Price $58.48(61% off)61% off.$150.00Comparable value $150.00(6) Only a few left
AquataliaEdwin Weatherproof Lace-Up Boot (Men)$179.96Current Price $179.96(68% off)68% off.$575.00Comparable value $575.00New Markdown Only a few left
Bruno MagliRafael Chelsea Boot (Men)$132.96Current Price $132.96(70% off)70% off.$450.00Comparable value $450.00New Markdown(1) Only a few left
Eastland'Seneca' Moc Toe Boot (Men)$74.96Current Price $74.96(40% off)40% off.$125.00Comparable value $125.00