AriatSpitfire Leather Chukka Boot (Men)$69.97Current Price $69.97(50% off)50% off.$139.95Comparable value $139.95(53)
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)
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)
NewClarks®Torhill Lo Chukka Boot (Men)$69.97Current Price $69.97(46% off)46% off.$130.00Comparable value $130.00
NewUGG®Chukka Lug Boot (Men)$89.97Current Price $89.97(40% off)40% off.$150.00Comparable value $150.00 Only a few left
ECCOLite Hybrid Chukka Boot (Men)$79.97Current Price $79.97(42% off)42% off.$140.00Comparable value $140.00
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)
VINTAGE FOUNDRYMarlow Chukka Boot (Men)$54.97Current Price $54.97(70% off)70% off.$185.00Comparable value $185.00
NUNN BUSHOtto Chukka Boot - Wide Width Available (Men)$69.97 – $79.97Current Price $69.97 to $79.97(Up to 27% off)Up to 27% off.$95.00 – $110.00Comparable value $95.00 to $110.00(14)
AriatSpitfire All Terrain Waterproof Chukka Boot (Men)$89.97Current Price $89.97(47% off)47% off.$169.95Comparable value $169.95(11)
Thomas & VineBanks Moc Toe Chukka Boot (Men)$54.97Current Price $54.97(71% off)71% off.$189.99Comparable value $189.99(1)
AriatSpitfire Leather Chukka Boot (Men)$59.97Current Price $59.97(53% off)53% off.$129.95Comparable value $129.95(331)
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)
Anthony VeerBushwick Chukka Boot (Men)$74.97Current Price $74.97(48% off)48% off.$145.99Comparable value $145.99(1)
Thomas & VineKeegan Chukka Boot$79.97Current Price $79.97(23% off)23% off.$104.97Comparable value $104.97(2)
Dune LondonClaus Chukka Boot (Men)$89.97Current Price $89.97(52% off)52% off.$190.00Comparable value $190.00
Marc Joseph New YorkChicago Chukka Boot (Men)$79.97Current Price $79.97(58% off)58% off.$195.00Comparable value $195.00(1)
ALDOKenora Chukka Boot (Men)$59.97Current Price $59.97(53% off)53% off.$130.00Comparable value $130.00(3) Only a few left
Donald PlinerKingston Chukka Boot (Men)$139.97Current Price $139.97(56% off)56% off.$325.00Comparable value $325.00(3)
Cole HaanMorse GRANDFØAM Chukka Boot (Men)$97.47Current Price $97.47(55% off)55% off.$220.00Comparable value $220.00(8)
NUNN BUSHOzark II Chukka Boot (Men)$89.97Current Price $89.97(18% off)18% off.$110.00Comparable value $110.00(3)
Allen EdmondsDonovan Chukka Boot (Men)$129.98Current Price $129.98(73% off)73% off.$495.00Comparable value $495.00(4) Only a few left
Clarks®Walpath Waterproof Chukka Boot (Men)$99.97Current Price $99.97(23% off)23% off.$130.00Comparable value $130.00(2) Only a few left
MagnanniEddison Chukka Boot (Men)$249.97Current Price $249.97(46% off)46% off.$465.00Comparable value $465.00(3)
JOHNSTON & MURPHY COLLECTIONWelch Chukka Boot (Men)$76.48Current Price $76.48(71% off)71% off.$265.00Comparable value $265.00(9)
TimberlandAttleboro Mid Chukka Boot (Men)$69.97Current Price $69.97(46% off)46% off.$130.00Comparable value $130.00(5)
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)
Johnston & MurphyUpton Chukka (Men)$129.97Current Price $129.97(27% off)27% off.$179.00Comparable value $179.00
Allen EdmondsDowning Chukka Boot (Men)$169.97Current Price $169.97(65% off)65% off.$495.00Comparable value $495.00(11)
La MilanoAcross II Cap Toe Chukka Boot (Men)$79.97Current Price $79.97(20% off)20% off.$99.99Comparable value $99.99
NewAnthony VeerGeorge Chukka Boot (Men)$99.97Current Price $99.97(39% off)39% off.$165.95Comparable value $165.95(1)
Brooks BrothersClaremont Chukka (Men)$169.97Current Price $169.97(62% off)62% off.$449.00Comparable value $449.00(2)
VinceLafayette Chukka Boot (Men)$149.97 – $182.97Current Price $149.97 to $182.97(Up to 57% off)Up to 57% off.$350.00Comparable value $350.00
Cole Haan2.Zerogrand Chukka Boot (Men)$44.97 – $99.97Current Price $44.97 to $99.97(Up to 86% off select items)Up to 86% off select items.$338.00Comparable value $338.00(403) Only a few left
Allen EdmondsCaden Lug Sole Chukka Boot (Men)$199.97Current Price $199.97(63% off)63% off.$550.00Comparable value $550.00
TO BOOT NEW YORKJohnnie Chukka Boot (Men)$199.97Current Price $199.97(52% off)52% off.$425.00Comparable value $425.00
Donald PlinerKingston Chukka Boot (Men)$149.97Current Price $149.97(53% off)53% off.$325.00Comparable value $325.00(2) Only a few left
Bruno MagliMabelton Chukka Boot (Men)$179.97Current Price $179.97(57% off)57% off.$425.00Comparable value $425.00 Only a few left
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)
VinceDann Lugged Chukka Boot (Men)$159.97Current Price $159.97(57% off)57% off.$375.00Comparable value $375.00(4)
VITTORIO RUSSOWhitman Chukka Boot (Men)$129.97Current Price $129.97(42% off)42% off.$225.00Comparable value $225.00(3)
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)
ROANTimothy Suede Chukka Boot$69.97Current Price $69.97(29% off)29% off.$99.00Comparable value $99.00(2)
TO BOOT NEW YORKHorace Chukka Boot (Men)$199.97Current Price $199.97(52% off)52% off.$425.00Comparable value $425.00
BarbourTucker Chukka Boot (Men)$82.47Current Price $82.47(61% off)61% off.$215.00Comparable value $215.00 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 & MurphyHenson XC4 Waterproof Chukka Boot (Men)$99.97Current Price $99.97(49% off)49% off.$199.00Comparable value $199.00(18) Only a few left
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 BUSHDenali Waterproof Plain Toe Boot - Wide Width Available$99.97Current Price $99.97(16% off)16% off.$120.00Comparable value $120.00(1)
UGG®Hayden Chukka Boot (Men)$99.97Current Price $99.97(33% off)33% off.$150.00Comparable value $150.00(5) Only a few left
Ben ShermanThames Chukka Boot (Men)$59.97Current Price $59.97(40% off)40% off.$100.00Comparable value $100.00 Only a few left
FERRAGAMOGiasone Ankle Chukka Boot (Men)$379.97Current Price $379.97(60% off)60% off.$950.00Comparable value $950.00
NewVinceJerome Chukka Boot (Men)$149.97Current Price $149.97(49% off)49% off.$295.00Comparable value $295.00
Anthony VeerWilson Chukka Boot (Men)$139.97Current Price $139.97(40% off)40% off.$234.95Comparable value $234.95(1)
NewClarks®Wallabee Genuine Calf Hair Chukka (Men)$99.97Current Price $99.97(44% off)44% off.$180.00Comparable value $180.00
Maison ForteDaytona Chukka Boot (Men)$109.97Current Price $109.97(43% off)43% off.$195.00Comparable value $195.00(3) Only a few left
NewClarks® OriginalsWallabee Chukka Boot (Men)$89.97Current Price $89.97(43% off)43% off.$160.00Comparable value $160.00
NewClarks® OriginalsWallabee Scout Chukka Boot (Men)$139.97Current Price $139.97(Up to 51% off)Up to 51% off.$270.00 – $290.00Comparable value $270.00 to $290.00
Donald PlinerSeya Chukka Boot (Men)$139.97Current Price $139.97(56% off)56% off.$325.00Comparable value $325.00(1)
NewClarks®Wallabee Chukka (Men)$79.97Current Price $79.97(52% off)52% off.$170.00Comparable value $170.00
TO BOOT NEW YORKVinny Chukka Boot (Men)$199.97Current Price $199.97(52% off)52% off.$425.00Comparable value $425.00(2) Only a few left
CARLOS SANTANACorazon Chukka Boot (Men)$109.97Current Price $109.97(38% off)38% off.$179.00Comparable value $179.00(1)
MagnanniLello Castagna Suede Boot (Men)$249.97Current Price $249.97(47% off)47% off.$475.00Comparable value $475.00
Tod'sIdeal Suede Chukka Boot (Men)$249.97Current Price $249.97(57% off)57% off.$595.00Comparable value $595.00(1)
SantoniGregory Chukka Boot (Men)$344.96Current Price $344.96(61% off)61% off.$890.00Comparable value $890.00(1) Only a few left
MagnanniOslo Schore Chukka Boot (Men)$239.97Current Price $239.97(49% off)49% off.$475.00Comparable value $475.00(1)
MagnanniSuede Chukka Boot (Men)$239.97Current Price $239.97(51% off)51% off.$495.00Comparable value $495.00