VANCE COSlater Chelsea Boot (Men)$74.97Current Price $74.97(31% off)31% off.$109.99Comparable value $109.99(1)
Clarks®Weltridge Side Zip Boot (Men)$94.97Current Price $94.97(26% off)26% off.$130.00Comparable value $130.00(3)
FlorsheimChalet Chelsea Boot (Men)$99.97Current Price $99.97(31% off)31% off.$145.00Comparable value $145.00(121)
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)
NewVANCE COJosiah Chelsea Boot (Men)$84.97Current Price $84.97(22% off)22% off.$109.99Comparable value $109.99
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(16)
Dune LondonCian Side Zip Boot (Men)$89.97Current Price $89.97(52% off)52% off.$190.00Comparable value $190.00
VANCE COStratton Chukka Boot (Men)$74.97Current Price $74.97(31% off)31% off.$109.99Comparable value $109.99(1)
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)
MADDENTaskorn Combat Boot (Men)$54.97Current Price $54.97(38% off)38% off.$90.00Comparable value $90.00(11)
Dune LondonClaus Chukka Boot (Men)$89.97Current Price $89.97(52% off)52% off.$190.00Comparable value $190.00
MADDENTaskorn Combat Boot (Men)$54.97Current Price $54.97(38% off)38% off.$90.00Comparable value $90.00(50)
Tommy HilfigerSesame Chelsea Boot (Men)$54.97Current Price $54.97(53% off)53% off.$119.00Comparable value $119.00(40)
FryeTyler Plain Toe Boot (Men)$139.97Current Price $139.97(57% off)57% off.$328.00Comparable value $328.00(90)
AboundWilder Chelsea Boot (Men)$49.97Current Price $49.97(44% off)44% off.$89.95Comparable value $89.95(7)
adidasTerrex Anylander Mid R.RDY Waterproof Hiking Boot (Men)$79.97Current Price $79.97(20% off)20% off.$100.00Comparable value $100.00(540)
Johnston & MurphyUpton Chukka (Men)$129.97Current Price $129.97(27% off)27% off.$179.00Comparable value $179.00
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)
AriatBarrett Almond Toe Boot (Men)$159.97Current Price $159.97(38% off)38% off.$259.95Comparable value $259.95(4)
Ariat'Lookout' Moc Toe Boot (Men)$79.97Current Price $79.97(50% off)50% off.$159.95Comparable value $159.95(70)
AriatWexford Chelsea Boot (Men)$99.97Current Price $99.97(47% off)47% off.$189.95Comparable value $189.95(4)
Dockers®Esmond Chukka Boot (Men)$59.97Current Price $59.97(36% off)36% off.$95.00Comparable value $95.00(5)
NewSORELSlabtown '62™ Waterproof Moc Toe Boot (Men)$99.97Current Price $99.97(42% off)42% off.$175.00Comparable value $175.00(11)
Steve MaddenPeter Boot (Men)$67.47Current Price $67.47(60% off)60% off.$170.00Comparable value $170.00(3)
Tommy HilfigerGainsly Chelsea Boot (Men)$59.97Current Price $59.97(52% off)52% off.$125.00Comparable value $125.00(2)
VINTAGE FOUNDRYMartin Chelsea Boot (Men)$49.97Current Price $49.97(71% off)71% off.$175.00Comparable value $175.00(7)
Johnston & MurphyUpton Chelsea Boot (Men)$129.97Current Price $129.97(27% off)27% off.$179.00Comparable value $179.00(7)
ECCOLite Hybrid Chukka Boot (Men)$79.97Current Price $79.97(42% off)42% off.$140.00Comparable value $140.00
NewAlignEddy Waterproof Leather Boot (Men)$99.97Current Price $99.97(44% off)44% off.$179.95Comparable value $179.95
BOSSNew Tunley Chelsea Boot (Men)$89.97 – $149.97Current Price $89.97 to $149.97(Up to 54% off)Up to 54% off.$199.00Comparable value $199.00(3)
Thomas & VineBanks Moc Toe Chukka Boot (Men)$54.97Current Price $54.97(71% off)71% off.$189.99Comparable value $189.99(1)
Anthony VeerBushwick Chukka Boot (Men)$74.97Current Price $74.97(48% off)48% off.$145.99Comparable value $145.99(1)
VINTAGE FOUNDRYBlaise Ankle Boot (Men)$49.97 – $99.97Current Price $49.97 to $99.97(Up to 81% off)Up to 81% off.$269.00Comparable value $269.00
BOSSColby Chelsea Boot (Men)$149.97Current Price $149.97(24% off)24% off.$199.00Comparable value $199.00(2)
NewMerrellTempo Sol Waterproof Mid Top Hiking Boot (Men)$59.97Current Price $59.97(25% off)25% off.$80.00Comparable value $80.00(1)
NUNN BUSHDelton Plain Toe Chukka Boot (Men)$54.97Current Price $54.97(42% off)42% off.$95.00Comparable value $95.00
NUNN BUSHOzark II Chukka Boot (Men)$89.97Current Price $89.97(18% off)18% off.$110.00Comparable value $110.00(3)
AriatDowntown Western Boot (Men)$129.97Current Price $129.97(50% off)50% off.$259.95Comparable value $259.95(25)
Dockers®Esmond Plain Toe Chukka Boot (Men)$59.97Current Price $59.97(29% off)29% off.$85.00Comparable value $85.00(10)
NewAlignEddy Waterproof Leather Boot (Men)$99.97Current Price $99.97(44% off)44% off.$179.95Comparable value $179.95
Allen EdmondsDowning Chukka Boot (Men)$169.97Current Price $169.97(65% off)65% off.$495.00Comparable value $495.00(11)
Anthony VeerRanveer Cap Toe Boot (Men)$159.97Current Price $159.97(38% off)38% off.$259.00Comparable value $259.00(1)
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)
AriatRidgeback Round Toe Cowboy Boot (Men)$109.97Current Price $109.97(50% off)50% off.$219.95Comparable value $219.95(10)
FlorsheimChalet Leather Cap Toe Boot (Men)$82.47Current Price $82.47(46% off)46% off.$155.00Comparable value $155.00(22)
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)
VITTORIO RUSSOWhitman Chukka Boot (Men)$129.97Current Price $129.97(42% off)42% off.$225.00Comparable value $225.00(3)
Tommy HilfigerBlaze Lace Cap Toe Boot (Men)$59.97Current Price $59.97(49% off)49% off.$119.00Comparable value $119.00
Dockers®Truman Chelsea Boot (Men)$59.97Current Price $59.97(36% off)36% off.$95.00Comparable value $95.00(5)
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)
AboundNash Chelsea Boot (Men)$59.97Current Price $59.97(33% off)33% off.$89.95Comparable value $89.95
Tommy HilfigerHarbin Chukka Boot (Men)$38.98 – $59.97Current Price $38.98 to $59.97(Up to 67% off select items)Up to 67% off select items.$119.00Comparable value $119.00(10)
NUNN BUSHKarnak Water Resistant Plain Toe Boot (Men)$89.97Current Price $89.97(18% off)18% off.$110.00Comparable value $110.00
NewSperryCold Bay Duck Boot (Men)$49.97Current Price $49.97(58% off)58% off.$120.00Comparable value $120.00
TO BOOT NEW YORKJohnnie Chukka Boot (Men)$199.97Current Price $199.97(52% off)52% off.$425.00Comparable value $425.00
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)
Clarks®Shepton Easy Chelsea Boot (Men)$94.97Current Price $94.97(26% off)26% off.$130.00Comparable value $130.00
VANCE COGarrett Cap Chelsea Boot - Wide Width (Men)$44.97Current Price $44.97(55% off)55% off.$99.99Comparable value $99.99(1)
SORELCheyanne Metro II Waterproof Duck Boot (Men)$59.96Current Price $59.96(60% off)60% off.$150.00Comparable value $150.00(8) Only a few left
VinceDominic Plain Toe Boot (Men)$169.97Current Price $169.97(56% off)56% off.$395.00Comparable value $395.00(5)
NewMerrellSpeed 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(21)
Allen EdmondsGrady Chukka Boot (Men)$189.97 – $249.97Current Price $189.97 to $249.97(Up to 65% off)Up to 65% off.$550.00Comparable value $550.00
NUNN BUSHOdell II Wingtip Boot (Men)$89.97Current Price $89.97(18% off)18% off.$110.00Comparable value $110.00(2)
NUNN BUSHKarnak Water Resistant Moc Toe Boot (Men)$89.97Current Price $89.97(18% off)18% off.$110.00Comparable value $110.00(3)
NewSwimsVigo Waterproof Boot (Men)$179.97Current Price $179.97(39% off)39% off.$298.00Comparable value $298.00
AriatSlingshot Cowboy Boot (Men)$119.97Current Price $119.97(50% off)50% off.$239.95Comparable value $239.95(119)
LeeWaylon Lace-Up Boot (Men)$74.97Current Price $74.97(25% off)25% off.$100.00Comparable value $100.00
NewMerrellMoab Speed 2 Waterproof Hiking Boot (Men)$109.97Current Price $109.97(42% off)42% off.$190.00Comparable value $190.00(31)
NewBirkenstockBend Chelsea Boot (Men)$99.97Current Price $99.97(41% off)41% off.$170.00Comparable value $170.00
NewAriatOakwood Cowboy Boot (Men)$139.97Current Price $139.97(46% off)46% off.$259.95Comparable value $259.95(78)
NUNN BUSHChase Plain Toe Chukka Boot - Wide Width Available (Men)$19.99 – $54.97Current Price $19.99 to $54.97(Up to 78% off select items)Up to 78% off select items.$95.00Comparable value $95.00(14)