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 $130.00(10)
NUNN BUSHKarnak Plain Toe Chelsea Boot (Men)$58.48 – $89.97Current Price $58.48 to $89.97(Up to 51% off select items)Up to 51% off select items.$120.00Comparable value $120.00
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 $175.00(17)
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 $90.00(14)
VANCE COAustin Cap Toe Chukka Boot - Wide Width (Men)$39.99 – $59.97Current Price $39.99 to $59.97(Up to 55% off select items)Up to 55% off select items.$89.99Comparable value $89.99(3)
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 $130.00(13)
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)
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 $160.00(7)
NUNN BUSHDelton Plain Toe Chelsea Boot (Men)$34.99 – $41.22Current Price $34.99 to $41.22(Up to 63% off)Up to 63% off.$95.00Comparable value $95.00
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 $135.00(2)
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 $200.00(8) Only a few left
NUNN BUSHOtis II Chelsea Boot (Men)$58.48 – $89.97Current Price $58.48 to $89.97(Up to 51% off select items)Up to 51% off select items.$110.00 – $120.00Comparable value $110.00 to $120.00(1)
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 $195.00(6)
SORELMadson II Chore Waterproof Boot (Men)$49.98Current Price $49.98(74% off)74% off.$195.00Comparable value $195.00(12) Only a few left
Cole HaanGrand Lug Sole Boot (Men)$64.98Current Price $64.98(51% off)51% off.$135.00Comparable value $135.00(2) Only a few left
Steve MaddenAddis Brogue Boot (Men)$63.72Current Price $63.72(56% off)56% off.$145.00Comparable value $145.00(1)
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 $230.00(15)
Cole HaanGrand Atlantic Chukka Boot - Wide Width Available (Men)$44.97Current Price $44.97(77% off)77% off.$200.00Comparable value $200.00(43)
Steve MaddenPeter Boot (Men)$67.47Current Price $67.47(60% off)60% off.$170.00Comparable value $170.00(3)
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(6)
Cole HaanMorse GRANDFØAM Chukka Boot (Men)$58.48 – $97.47Current Price $58.48 to $97.47(Up to 73% off)Up to 73% off.$220.00Comparable value $220.00(8)
NUNN BUSH1912 Plain Toe Chelsea Boot (Men)$49.99Current Price $49.99(56% off)56% off.$115.00Comparable value $115.00(2)
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 $160.00(1)
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 $120.00(6)
ALDODarionn Waterproof Lace-Up Cap Toe Boot (Men)$58.48Current Price $58.48(66% off)66% off.$175.00Comparable value $175.00(2)
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 $130.00(7)
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 $130.00(3)
VITTORIO RUSSOWade Boot (Men)$97.47Current Price $97.47(56% off)56% off.$225.00Comparable value $225.00(2)
Gino VitaleWingtip Chelsea Boot (Men)$62.96 – $89.97Current Price $62.96 to $89.97(Up to 60% off select items)Up to 60% off select items.$159.99Comparable value $159.99
FlorsheimChalet Leather Cap Toe Boot (Men)$82.47Current Price $82.47(46% off)46% off.$155.00Comparable value $155.00(22)
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
Steve MaddenRilyn Chelsea Boot (Men)$59.96Current Price $59.96(62% off)62% off.$160.00Comparable value $160.00(16)
Eastland'Lumber Up' Moc Toe Boot (Men)$74.96 – $99.97Current Price $74.96 to $99.97(Up to 50% off select items)Up to 50% off select items.$135.00 – $150.00Comparable value $135.00 to $150.00(5)
TimberlandAttleboro Chelsea Boot (Men)$49.99Current Price $49.99(64% off)64% off.$140.00Comparable value $140.00(10) Only a few left
EastlandChimney Pond Chelsea Boot (Men)$74.96Current Price $74.96(48% off)48% off.$145.00Comparable value $145.00 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 $125.00(8)
SORELHi-Line Waterproof Lace-Up Boot (Men)$62.96Current Price $62.96(65% off)65% off.$185.00Comparable value $185.00(33) Only a few left
Cole HaanChamberlin Grand Chukka Boot (Men)$97.47Current Price $97.47(66% off)66% off.$290.00Comparable value $290.00(10)
Johnston & MurphyLewis Chelsea Boot (Men)$49.99Current Price $49.99(61% off)61% off.$129.00Comparable value $129.00(7)
Ted Baker LondonRemington Chelsea Boot (Men)$77.98Current Price $77.98(64% off)64% off.$220.00Comparable value $220.00(2) Only a few left
FryeBowery Chelsea Boot (Men)$116.98Current Price $116.98(64% off)64% off.$328.00Comparable value $328.00(29) Only a few left
Johnston & MurphyBrody Chelsea Boot (Men)$49.99Current Price $49.99(69% off)69% off.$165.00Comparable value $165.00(19)
Eastland'Seneca' Moc Toe Boot (Men)$74.96Current Price $74.96(40% off)40% off.$125.00Comparable value $125.00
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)
NewAllen EdmondsDallas Western Boot (Men)$129.98Current Price $129.98(78% off)78% off.$595.00Comparable value $595.00
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(4) Only a few left
SORELCyprus™ Waterproof Chelsea Boot (Men)$74.99Current Price $74.99(40% off)40% off.$125.00Previous Price $125.00 Only a few left
AquataliaGitano Genuine Shearling Lined Water Repellent Boot (Men)$194.96Current Price $194.96(68% off)68% off.$625.00Comparable value $625.00(3)
BarbourTucker Chukka Boot (Men)$82.47Current Price $82.47(61% off)61% off.$215.00Comparable value $215.00 Only a few left
DEARFOAMSShepparton Genuine Shearling Boot (Men)$49.99Current Price $49.99(61% off)61% off.$130.00Comparable value $130.00(15)
SantoniGregory Chukka Boot (Men)$344.96Current Price $344.96(61% off)61% off.$890.00Comparable value $890.00(1) Only a few left
FlorsheimForge Lace-Up Boot (Men)$82.47Current Price $82.47(38% off)38% off.$135.00Comparable value $135.00(1) Only a few left
JOHNSTON & MURPHY COLLECTIONWelch Chukka Boot (Men)$76.48Current Price $76.48(71% off)71% off.$265.00Comparable value $265.00(9)
BOSSColby Chelsea Boot (Men)$97.48Current Price $97.48(51% off)51% off.$199.00Comparable value $199.00(1) Only a few left
AquataliaFortino Water Repellent Boot (Men)$149.99 – $259.97Current Price $149.99 to $259.97(Up to 76% off select items)Up to 76% off select items.$625.00Comparable value $625.00(3)
Steve MaddenRoswel Plain Toe Chelsea Boot (Men)$67.47Current Price $67.47(51% off)51% off.$140.00Comparable value $140.00
FlorsheimAzzano Plain Toe Chelsea Boot (Men)$82.47Current Price $82.47(43% off)43% off.$145.00Comparable value $145.00(2) Only a few left
FlorsheimForge Chelsea Boot (Men)$82.47Current Price $82.47(36% off)36% off.$130.00Comparable value $130.00(3) Only a few left
Bruno MagliRafael Chelsea Boot (Men)$132.96Current Price $132.96(70% off)70% off.$450.00Comparable value $450.00(1) Only a few left
MagnanniKam II Boot (Men)$181.98Current Price $181.98(63% off)63% off.$495.00Comparable value $495.00(7) Only a few left
MagnanniKam Chelsea Boot (Men)$199.99Current Price $199.99(59% off)59% off.$495.00Comparable value $495.00(2) Only a few left
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 $495.00(37) Only a few left
Stuart WeitzmanAdwin Chelsea Boot (Men)$324.98Current Price $324.98(66% off)66% off.$975.00Comparable value $975.00(4)
MagnanniEddison Chelsea Boot (Men)$187.47Current Price $187.47(59% off)59% off.$465.00Comparable value $465.00(2) Only a few left