New MarkdownFryeBowery Chelsea Boot (Men)$125.96 – $179.97Current Price $125.96 to $179.97(Up to 61% off select items)Up to 61% off select items.$328.00Comparable value $328.00(26)
Allen EdmondsWren Chelsea Boot (Men)$159.97Current Price $159.97(67% off)67% off.$495.00Comparable value $495.00(4)
Allen EdmondsDriggs Chelsea Boot (Men)$199.97Current Price $199.97(59% off)59% off.$495.00Comparable value $495.00(2)
New MarkdownSteve MaddenSawyer Chelsea Boot (Men)$34.96 – $49.97Current Price $34.96 to $49.97(Up to 61% off select items)Up to 61% off select items.$90.00Comparable value $90.00(10)
New MarkdownMagnanniBurlo Leather Chelsea Boot (Men)$137.48 – $249.97Current Price $137.48 to $249.97(Up to 69% off select items)Up to 69% off select items.$450.00Comparable value $450.00(32)
Cole HaanNewmark Grand Water Resistant Chelsea Boot (Men)$129.97Current Price $129.97(63% off)63% off.$360.00Comparable value $360.00(7)
Roberto CavalliHuston Chelsea Boot (Men)$159.97Current Price $159.97(70% off)70% off.$545.00Comparable value $545.00(3)
New!Johnston & MurphyUpton Chelsea Boot (Men)$129.97Current Price $129.97(27% off)27% off.$179.00Comparable value $179.00(6)
New MarkdownMagnanniKam Chelsea Boot (Men)$181.98 – $279.97Current Price $181.98 to $279.97(Up to 63% off select items)Up to 63% off select items.$495.00Comparable value $495.00(1)
Cole HaanChamberlin Grand Water Resistant Chelsea Boot (Men)$129.97Current Price $129.97(50% off)50% off.$260.00Comparable value $260.00(8)
New!AboundNash Chelsea Boot (Men)$59.97Current Price $59.97(33% off)33% off.$89.95Comparable value $89.95
New!FlorsheimChalet Chelsea Boot (Men)$99.97Current Price $99.97(31% off)31% off.$145.00Comparable value $145.00(114)
BOSSColby Chelsea Boot (Men)$149.97Current Price $149.97(24% off)24% off.$199.00Comparable value $199.00(2)
New MarkdownMagnanniBonn Leather Chelsea Boot (Men)$195.96 – $279.97Current Price $195.96 to $279.97(Up to 60% off select items)Up to 60% off select items.$495.00Comparable value $495.00(7)
New MarkdownVITTORIO RUSSOPeter Chelsea Boot (Men)$84.48 – $129.97Current Price $84.48 to $129.97(Up to 62% off select items)Up to 62% off select items.$225.00Comparable value $225.00(3)
AquataliaEnrico Chelsea Boot (Men)$229.97Current Price $229.97(58% off)58% off.$550.00Comparable value $550.00
New MarkdownTO BOOT NEW YORKDressel Chelsea Boot (Men)$149.96 – $199.97Current Price $149.96 to $199.97(Up to 68% off select items)Up to 68% off select items.$475.00Comparable value $475.00(1)
AllSaintsCreed Chelsea Boot (Men)$139.97Current Price $139.97(53% off)53% off.$299.00Comparable value $299.00(2)Only a few left
New MarkdownStuart WeitzmanAdwin Chelsea Boot (Men)$209.97 – $324.98Current Price $209.97 to $324.98(Up to 78% off)Up to 78% off.$975.00Comparable value $975.00(2)
AllSaintsHarley Chelsea Boot (Men)$129.97Current Price $129.97(56% off)56% off.$299.00Comparable value $299.00(24)
FryeDylan Chelsea Boot (Men)$189.97Current Price $189.97(52% off)52% off.$398.00Comparable value $398.00(13)
Tommy HilfigerSesame Chelsea Boot (Men)$54.97Current Price $54.97(53% off)53% off.$119.00Comparable value $119.00(32)
New MarkdownJohnston & MurphyBorland Chelsea Boot (Men)$55.96 – $79.97Current Price $55.96 to $79.97(Up to 65% off select items)Up to 65% off select items.$160.00Comparable value $160.00(1)
New MarkdownVinceBonham Water Repellent Chelsea Boot (Men)$99.99Current Price $99.99(71% off)71% off.$350.00Comparable value $350.00(1)
Dr. Martens2976 Wintergrip Water Resistant Chelsea Boot (Men)$99.97Current Price $99.97(47% off)47% off.$190.00Comparable value $190.00(48)
New MarkdownSORELSlabtown 62 Waterproof Chelsea Boot (Men)$74.96Current Price $74.96(55% off)55% off.$170.00Comparable value $170.00(1)Only a few left
Roberto CavalliCrip Chelsea Boot (Men)$159.97Current Price $159.97(71% off)71% off.$570.00Comparable value $570.00(1)
New!Ted BakerNorwich Chelsea Boot (Men)$89.97Current Price $89.97(52% off)52% off.$190.00Comparable value $190.00
New MarkdownMagnanniEddison Chelsea Boot (Men)$149.99 – $249.97Current Price $149.99 to $249.97(Up to 67% off select items)Up to 67% off select items.$465.00Comparable value $465.00
FERRAGAMOChelsea Boot (Men)$499.97Current Price $499.97(60% off)60% off.$1,250.00Comparable value $1,250.00(2)
New MarkdownCole HaanChamberlin Grand Chelsea Boot (Men)$97.47Current Price $97.47(62% off)62% off.$260.00Comparable value $260.00(1)
Bruno MagliNello Chelsea Boot (Men)$199.97Current Price $199.97(49% off)49% off.$395.00Comparable value $395.00
MADDENEstiban Chelsea Boot (Men)$54.97Current Price $54.97(35% off)35% 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
New MarkdownBOSSColby Chelsea Boot (Men)$97.48 – $149.97Current Price $97.48 to $149.97(Up to 51% off select items)Up to 51% off select items.$199.00Comparable value $199.00
New!SperryClifton Waterproof Chelsea Duck Boot (Men)$49.97Current Price $49.97(54% off)54% off.$110.00Comparable value $110.00Only a few left
New!ALDOLangton Chelsea Boot (Men)$74.97Current Price $74.97(50% off)50% off.$150.00Comparable value $150.00
Donald PlinerCroc Embossed Leather Chelsea Boot (Men)$139.97Current Price $139.97(57% off)57% off.$328.00Comparable value $328.00(4)
New!SantoniChelsea Boot (Men)$739.97Current Price $739.97(52% off)52% off.$1,570.00Comparable value $1,570.00Only a few left
New MarkdownFlorsheimRuvo Chelsea Boot (Men)$82.47Current Price $82.47(45% off)45% off.$150.00Comparable value $150.00(22)
New!Clarks®Jaxen Easy Chelsea Boot (Men)$99.97Current Price $99.97(16% off)16% off.$120.00Comparable value $120.00
TO BOOT NEW YORKCharleston Chelsea Boot (Men)$199.97Current Price $199.97(52% off)52% off.$425.00Comparable value $425.00(2)
FryeTyler Chelsea Boot (Men)$149.97Current Price $149.97(41% off)41% off.$258.00Comparable value $258.00(34)
Ted Baker LondonRemington Chelsea Boot (Men)$119.97Current Price $119.97(45% off)45% off.$220.00Comparable value $220.00(2)
New MarkdownTimberlandAttleboro Chelsea Boot (Men)$49.99 – $69.97Current Price $49.99 to $69.97(Up to 61% off select items)Up to 61% off select items.$130.00 – $140.00Comparable value $130.00 to $140.00(7)
New!ALDOWynford Chelsea Boot (Men)$74.97Current Price $74.97(50% off)50% off.$150.00Comparable value $150.00
Steve MaddenRilyn Chelsea Boot (Men)$79.97Current Price $79.97(50% off)50% off.$160.00Comparable value $160.00(13)
New MarkdownCole HaanGrand Atlantic Chelsea Boot (Men)$74.96 – $99.97Current Price $74.96 to $99.97(Up to 62% off select items)Up to 62% off select items.$200.00Comparable value $200.00(3)
New!BarbourStorm Chelsea Rain Boot (Men)$69.97Current Price $69.97(51% off)51% off.$145.00Comparable value $145.00(1)
BOSSNew Tunley Chelsea Boot (Men)$149.97Current Price $149.97(24% off)24% off.$199.00Comparable value $199.00
New!GREATSDante Chelsea Boot (Men)$69.97Current Price $69.97(72% off)72% off.$250.00Comparable value $250.00Only a few left
New MarkdownDockers®Truman Chelsea Boot (Men)$44.96 – $59.97Current Price $44.96 to $59.97(Up to 52% off select items)Up to 52% off select items.$95.00Comparable value $95.00(2)
New MarkdownSteve MaddenRoswel Plain Toe Chelsea Boot (Men)$67.47Current Price $67.47(51% off)51% off.$140.00Comparable value $140.00
New!McQueenTrunk Chelsea Boot (Men)$479.97Current Price $479.97(65% off)65% off.$1,390.00Comparable value $1,390.00Only a few left
New!Allen EdmondsDriggs Chelsea Boot (Men)$189.97Current Price $189.97(65% off)65% off.$550.00Comparable value $550.00
New MarkdownSteve MaddenEmden Lug Sole Chelsea Boot (Men)$55.96Current Price $55.96(60% off)60% off.$140.00Comparable value $140.00
FERRAGAMOLoreno Chelsea Boot (Men)$659.97Current Price $659.97(48% off)48% off.$1,290.00Comparable value $1,290.00
Allen EdmondsAlgonquin Lugged Chelsea Boot (Men)$299.97Current Price $299.97(39% off)39% off.$495.00Comparable value $495.00
New MarkdownCole HaanNewmark Grand Chelsea Boot (Men)$97.47Current Price $97.47(72% off)72% off.$360.00Comparable value $360.00
New!Tommy HilfigerGainsly Chelsea Boot (Men)$59.97Current Price $59.97(52% off)52% off.$125.00Comparable value $125.00
Bruno MagliMaximo Chelsea Boot (Men)$199.97Current Price $199.97(55% off)55% off.$450.00Comparable value $450.00
AboundWilder Chelsea Boot (Men)$49.97Current Price $49.97(37% off)37% off.$79.95Comparable value $79.95(6)
New!GREATSBowery Chelsea Boot (Men)$49.97Current Price $49.97(74% off)74% off.$199.00Comparable value $199.00Only a few left
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)
Allen EdmondsLiverpool Chelsea Boot (Men)$199.97Current Price $199.97(59% off)59% off.$495.00Comparable value $495.00(50)
New MarkdownJohnston & MurphyJenson Chelsea Boot (Men)$136.48Current Price $136.48(58% off)58% off.$328.00Comparable value $328.00(3)
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)
Maison ForteEnzo Croc Embossed Chelsea Boot (Men)$109.97Current Price $109.97(51% off)51% off.$225.00Comparable value $225.00(3)Only a few left
Tommy HilfigerRoklan Chelsea Boot (Men)$59.97Current Price $59.97(53% off)53% off.$129.00Comparable value $129.00
New!Steve MaddenFenton Lug Sole Chelsea Boot (Men)$79.97Current Price $79.97(38% off)38% off.$130.00Comparable value $130.00(4)
Tommy HilfigerBerton Chelsea Boot (Men)$59.97Current Price $59.97(49% off)49% off.$119.00Comparable value $119.00
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)