Clear The RackJohnston & MurphyBoswell Chukka Boot (Men)$43.86 – $50.60Current Price $43.86 to $50.60(Extra 25% off)Includes extra 25% off.$58.48 – $67.47Previous Price $58.48 to $67.47$175.00Comparable value $175.00(15)
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)
Dune LondonClaus Chukka Boot (Men)$89.97Current Price $89.97(52% off)52% off.$190.00Comparable value $190.00
Clear The RackCole HaanMorse GRANDFØAM Chukka Boot (Men)$63.36 – $73.10Current Price $63.36 to $73.10(Extra 25% off)Includes extra 25% off.$84.48 – $97.47Previous Price $84.48 to $97.47$220.00Comparable value $220.00(8)
Clear The RackCole HaanGrand Atlantic Chukka Boot - Wide Width Available (Men)$33.72Current Price $33.72(Extra 25% off)Includes extra 25% off.$44.97Previous Price $44.97$200.00Comparable value $200.00(43)
Clear The RackJOHNSTON & MURPHY COLLECTIONWelch Chukka Boot (Men)$57.36Current Price $57.36(Extra 25% off)Includes extra 25% off.$76.48Previous Price $76.48$265.00Comparable value $265.00(9)
Clear The RackNUNN BUSHChase Plain Toe Chukka Boot - Wide Width Available (Men)$14.99 – $54.97Current Price $14.99 to $54.97(Extra 25% off select items)Includes extra 25% off select items.$19.99Previous Price $19.99$95.00Comparable value $95.00(14)
Allen EdmondsDowning Chukka Boot (Men)$169.97Current Price $169.97(65% off)65% off.$495.00Comparable value $495.00(11)
Clear The RackTommy HilfigerHarbin Chukka Boot (Men)$29.23 – $59.97Current Price $29.23 to $59.97(Extra 25% off select items)Includes extra 25% off select items.$38.98Previous Price $38.98$119.00Comparable value $119.00(10)
Donald PlinerKingston Chukka Boot (Men)$139.97Current Price $139.97(56% off)56% off.$325.00Comparable value $325.00(3)
Clear The RackCole HaanChamberlin Grand Chukka Boot (Men)$73.10Current Price $73.10(Extra 25% off)Includes extra 25% off.$97.47Previous Price $97.47$290.00Comparable value $290.00(10)
NewAnthony VeerGeorge Chukka Boot (Men)$99.97Current Price $99.97(39% off)39% off.$165.95Comparable value $165.95(1)
TO BOOT NEW YORKJohnnie Chukka Boot (Men)$199.97Current Price $199.97(52% off)52% off.$425.00Comparable value $425.00
ECCOLite Hybrid Chukka Boot (Men)$79.97Current Price $79.97(42% off)42% off.$140.00Comparable value $140.00
Clear The RackNUNN BUSHOtto Chukka Boot - Wide Width Available (Men)$14.99 – $79.97Current Price $14.99 to $79.97(Extra 25% off select items)Includes extra 25% off select items.$19.99Previous Price $19.99$95.00 – $110.00Comparable value $95.00 to $110.00(14)
Clear The RackCole HaanGrand Remix Chukka Boot (Men)$56.22 – $99.97Current Price $56.22 to $99.97(Extra 25% off select items)Includes extra 25% off select items.$74.96Previous Price $74.96$220.00 – $230.00Comparable value $220.00 to $230.00(15)
VANCE COAustin Cap Toe Chukka Boot - Wide Width (Men)$39.99Current Price $39.99(55% off)55% off.$89.99Comparable value $89.99(3)
VANCE COStratton Chukka Boot (Men)$74.97Current Price $74.97(31% off)31% off.$109.99Comparable value $109.99(1)
Dockers®Esmond Chukka Boot (Men)$59.97Current Price $59.97(36% off)36% off.$95.00Comparable value $95.00(5)
Anthony VeerBushwick Chukka Boot (Men)$74.97Current Price $74.97(48% off)48% off.$145.99Comparable value $145.99(1)
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 & MurphyUpton Chukka (Men)$129.97Current Price $129.97(27% off)27% off.$179.00Comparable value $179.00
Marc Joseph New YorkChicago Chukka Boot (Men)$79.97Current Price $79.97(58% off)58% off.$195.00Comparable value $195.00(1)
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
ALDOKenora Chukka Boot (Men)$59.97Current Price $59.97(53% off)53% off.$130.00Comparable value $130.00(3) Only a few left
BarbourReadhead Chukka Boot (Men)$109.97Current Price $109.97(50% off)50% off.$220.00Comparable value $220.00(2) Only a few left
Clear The RackAllen EdmondsCarson Hybrid Chukka Boot (Men)$74.99 – $149.97Current Price $74.99 to $149.97(Extra 25% off select items)Includes extra 25% off select items.$99.99Previous Price $99.99$345.00Comparable value $345.00(34)
VITTORIO RUSSOWhitman Chukka Boot (Men)$129.97Current Price $129.97(42% off)42% off.$225.00Comparable value $225.00(3)
NUNN BUSHOzark II Chukka Boot (Men)$89.97Current Price $89.97(18% off)18% off.$110.00Comparable value $110.00(3)
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
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
NewClarks®Wallabee Chukka (Men)$79.97Current Price $79.97(52% off)52% off.$170.00Comparable value $170.00
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
NewClarks®Torhill Lo Chukka Boot (Men)$69.97Current Price $69.97(46% off)46% off.$130.00Comparable value $130.00
TO BOOT NEW YORKHorace Chukka Boot (Men)$199.97Current Price $199.97(52% off)52% off.$425.00Comparable value $425.00
LUGZConvoy Lace-Up Boot$49.97 – $54.97Current Price $49.97 to $54.97(Up to 37% off)Up to 37% off.$80.00Comparable value $80.00(2)
NUNN BUSHDelton Plain Toe Chukka Boot (Men)$54.97Current Price $54.97(42% off)42% off.$95.00Comparable value $95.00
Anthony VeerWilson Chukka Boot (Men)$139.97Current Price $139.97(40% off)40% off.$234.95Comparable value $234.95(1)
Tommy HilfigerBage Chukka Boot (Men)$59.97Current Price $59.97(49% off)49% off.$119.00Comparable value $119.00(6)
Dockers®Esmond Plain Toe Chukka Boot (Men)$59.97Current Price $59.97(29% off)29% off.$85.00Comparable value $85.00(10)
Bruno MagliMabelton Chukka Boot (Men)$179.97Current Price $179.97(57% off)57% off.$425.00Comparable value $425.00 Only a few left
Donald PlinerKingston Chukka Boot (Men)$149.97Current Price $149.97(53% off)53% off.$325.00Comparable value $325.00(2) Only a few left
NewAriatSpitfire All Terrain Waterproof Chukka Boot (Men)$89.97Current Price $89.97(47% off)47% off.$169.95Comparable value $169.95(11)
Deer StagsGarfield Plain Toe Chukka Boot (Men)$64.97Current Price $64.97(35% off)35% off.$100.00Comparable value $100.00 Only a few left
Clear The RackUGG®Neumel Shaggy Suede Chukka Boot (Men)$53.41Current Price $53.41(Extra 25% off)Includes extra 25% off.$71.22Previous Price $71.22$150.00Comparable value $150.00(2) Only a few left
VINTAGE FOUNDRYMarlow Chukka Boot (Men)$54.97Current Price $54.97(70% off)70% off.$185.00Comparable value $185.00 Only a few left
Tommy HilfigerBlaze Lace Cap Toe Boot (Men)$59.97Current Price $59.97(49% off)49% off.$119.00Comparable value $119.00
SKECHERSx John Deere Segment 2.0 Waterproof Chelsea Boot (Men)$59.97Current Price $59.97(53% off)53% off.$128.00Comparable value $128.00(1)
Clear The RackAllSaintsSkiff Chukka Boot (Men)$91.85Current Price $91.85(Extra 25% off)Includes extra 25% off.$122.47Previous Price $122.47$299.00Comparable value $299.00(1) Only a few left
AriatSpitfire Leather Chukka Boot (Men)$69.97Current Price $69.97(50% off)50% off.$139.95Comparable value $139.95(53)
Clear The RackClarks®Wallaston Chukka Boot (Men)$44.97 – $79.97Current Price $44.97 to $79.97(Extra 25% off select items)Includes extra 25% off select items.$59.96Previous Price $59.96$120.00Comparable value $120.00(5)
Clarks®Wallaston Low Chukka Sneaker (Men)$84.97Current Price $84.97(22% off)22% off.$110.00Comparable value $110.00
Thomas & VineKeegan Chukka Boot$79.97Current Price $79.97(23% off)23% off.$104.97Comparable value $104.97(2)
AriatSpitfire Leather Chukka Boot (Men)$59.97Current Price $59.97(53% off)53% off.$129.95Comparable value $129.95(331)
Brooks BrothersClaremont Chukka (Men)$169.97Current Price $169.97(62% off)62% off.$449.00Comparable value $449.00(2)
VinceDann Lugged Chukka Boot (Men)$159.97Current Price $159.97(57% off)57% off.$375.00Comparable value $375.00(4)
VINTAGE FOUNDRYAnderson Casual Chukka Boot (Men)$69.97Current Price $69.97(60% off)60% off.$175.00Comparable value $175.00 Only a few left
NUNN BUSHDenali Waterproof Plain Toe Boot - Wide Width Available$99.97Current Price $99.97(16% off)16% off.$120.00Comparable value $120.00(1)
Clarks®Walpath Waterproof Chukka Boot (Men)$99.97Current Price $99.97(23% off)23% off.$130.00Comparable value $130.00(2)
MagnanniEddison Chukka Boot (Men)$249.97Current Price $249.97(46% off)46% off.$465.00Comparable value $465.00(3)
TimberlandAttleboro Mid Chukka Boot (Men)$69.97Current Price $69.97(46% off)46% off.$130.00Comparable value $130.00(5)
La MilanoAcross II Cap Toe Chukka Boot (Men)$79.97Current Price $79.97(20% off)20% off.$99.99Comparable value $99.99
Allen EdmondsCaden Lug Sole Chukka Boot (Men)$199.97Current Price $199.97(63% off)63% off.$550.00Comparable value $550.00
Donald PlinerSeya Chukka Boot (Men)$139.97Current Price $139.97(56% off)56% off.$325.00Comparable value $325.00(1)
UGG®Neumel Chukka Boot (Men)$99.97Current Price $99.97(Up to 35% off)Up to 35% off.$150.00 – $155.00Comparable value $150.00 to $155.00(461) Only a few left
NewVinceJerome Chukka Boot (Men)$149.97Current Price $149.97(49% off)49% off.$295.00Comparable value $295.00
NewClarks®Wallabee FTR2 Moc Toe Chukka Boot (Men)$79.97Current Price $79.97(42% off)42% off.$140.00Comparable value $140.00
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
Clarks®Wallaston Low Chukka Boot (Men)$84.97Current Price $84.97(22% off)22% off.$110.00Comparable value $110.00(2)
NewClarks® OriginalsWallabee Chukka Boot (Men)$89.97Current Price $89.97(43% off)43% off.$160.00Comparable value $160.00
MagnanniLello Castagna Suede Boot (Men)$249.97Current Price $249.97(47% off)47% off.$475.00Comparable value $475.00