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 $175.00New Markdown(14)
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 $130.00New Markdown(3)
Cole HaanMorse GRANDFØAM Chukka Boot (Men)$84.48 – $97.47Current Price $84.48 to $97.47(Up to 61% off)Up to 61% off.$220.00Comparable value $220.00New Markdown(6)
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 $130.00New Markdown(10)
Cole HaanChamberlin Grand Chukka Boot (Men)$97.47Current Price $97.47(66% off)66% off.$290.00Comparable value $290.00New Markdown(8)
Deer StagsGarfield Plain Toe Chukka Boot (Men)$64.97Current Price $64.97(35% off)35% off.$100.00Comparable value $100.00
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)
ECCOLite Hybrid Chukka Boot (Men)$79.97Current Price $79.97(42% off)42% off.$140.00Comparable value $140.00
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 $338.00New Markdown(403) Only a few left
Dune LondonClaus Chukka Boot (Men)$89.97Current Price $89.97(52% off)52% off.$190.00Comparable value $190.00
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)
VINTAGE FOUNDRYMarlow Chukka Boot (Men)$54.97Current Price $54.97(70% off)70% off.$185.00Comparable value $185.00
NUNN BUSHOzark II Chukka Boot (Men)$89.97Current Price $89.97(18% off)18% off.$110.00Comparable value $110.00(3)
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 $95.00New Markdown(14)
Johnston & MurphyUpton Chukka (Men)$129.97Current Price $129.97(27% off)27% off.$179.00Comparable value $179.00
NUNN BUSHDenali Waterproof Plain Toe Boot - Wide Width Available$99.97Current Price $99.97(16% off)16% off.$120.00Comparable value $120.00(1)
VANCE COStratton Chukka Boot (Men)$74.97Current Price $74.97(31% off)31% off.$109.99Comparable value $109.99(1)
Allen EdmondsCaden Lug Sole Chukka Boot (Men)$199.97Current Price $199.97(63% off)63% off.$550.00Comparable value $550.00
Cole HaanGrand Atlantic Chukka Boot - Wide Width Available (Men)$44.97Current Price $44.97(77% off)77% off.$200.00Comparable value $200.00New Markdown(43)
Rodd & GunnPebbly Hill Chukka Boot (Men)$99.97Current Price $99.97(49% off)49% off.$198.00Comparable value $198.00(34) Only a few left
Johnston & MurphyUpton Chukka Boot (Men)$49.99Current Price $49.99(70% off)70% off.$169.00Comparable value $169.00(19)
JOHNSTON & MURPHY COLLECTIONWelch Chukka Boot (Men)$76.48Current Price $76.48(71% off)71% off.$265.00Comparable value $265.00New Markdown(9)
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 $230.00New Markdown(15)
TO BOOT NEW YORKHorace Chukka Boot (Men)$199.97Current Price $199.97(52% off)52% off.$425.00Comparable value $425.00
Donald PlinerKingston Chukka Boot (Men)$139.97Current Price $139.97(56% off)56% off.$325.00Comparable value $325.00(2)
FryeBowery Chukka Boot (Men)$139.97Current Price $139.97(59% off)59% off.$348.00Comparable value $348.00(53) Only a few left
NUNN BUSHOtto Chukka Boot - Wide Width Available (Men)$19.99 – $79.97Current Price $19.99 to $79.97(Up to 78% off select items)Up to 78% off select items.$95.00 – $110.00Comparable value $95.00 to $110.00New Markdown(14)
Dockers®Esmond Chukka Boot (Men)$59.97Current Price $59.97(36% off)36% off.$95.00Comparable value $95.00(5)
NUNN BUSHDelton Plain Toe Chukka Boot (Men)$54.97Current Price $54.97(42% off)42% off.$95.00Comparable value $95.00
NewVinceJerome Chukka Boot (Men)$149.97Current Price $149.97(49% off)49% off.$295.00Comparable value $295.00 Only a few left
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)
Allen EdmondsDonovan Chukka Boot (Men)$129.98Current Price $129.98(73% off)73% off.$495.00Comparable value $495.00New Markdown(3) Only a few left
NewMarc Joseph New YorkChicago Chukka Boot (Men)$79.97Current Price $79.97(58% off)58% off.$195.00Comparable value $195.00(1)
Thomas & VineKeegan Chukka Boot$79.97Current Price $79.97(23% off)23% off.$104.97Comparable value $104.97(2)
RESERVE FOOTWEARZion Chukka Boot (Men)$39.97Current Price $39.97(50% off)50% off.$80.00Comparable value $80.00(3)
Tommy HilfigerBlaze Lace Cap Toe Boot (Men)$59.97Current Price $59.97(49% off)49% off.$119.00Comparable value $119.00
Dockers®Esmond Plain Toe Chukka Boot (Men)$59.97Current Price $59.97(29% off)29% off.$85.00Comparable value $85.00(10)
La MilanoAcross II Cap Toe Chukka Boot (Men)$79.97Current Price $79.97(20% off)20% off.$99.99Comparable value $99.99
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 $120.00New Markdown(2)
VITTORIO RUSSOWhitman Chukka Boot (Men)$129.97Current Price $129.97(42% off)42% off.$225.00Comparable value $225.00(3)
Johnston & MurphyHenson XC4 Waterproof Chukka Boot (Men)$99.97Current Price $99.97(49% off)49% off.$199.00Comparable value $199.00(18)
Brooks BrothersClaremont Chukka (Men)$169.97Current Price $169.97(62% off)62% off.$449.00Comparable value $449.00(2)
VinceDann Lugged Chukka Boot (Men)$71.97 – $159.97Current Price $71.97 to $159.97(Up to 80% off select items)Up to 80% off select items.$375.00Comparable value $375.00New Markdown(4)
TO BOOT NEW YORKJohnnie Chukka Boot (Men)$199.97Current Price $199.97(52% off)52% off.$425.00Comparable value $425.00
NewClarks®Walpath Waterproof Chukka Boot (Men)$99.97Current Price $99.97(23% off)23% off.$130.00Comparable value $130.00(2)
Anthony VeerBushwick Chukka Boot (Men)$74.97Current Price $74.97(48% off)48% off.$145.99Comparable value $145.99(1)
Allen EdmondsDowning Chukka Boot (Men)$169.97Current Price $169.97(65% off)65% off.$495.00Comparable value $495.00(10)
NewLUGZConvoy 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)
VINTAGE FOUNDRYMilton Chukka Boot (Men)$59.97Current Price $59.97(66% off)66% off.$180.00Comparable value $180.00(3)
MagnanniEddison Chukka Boot (Men)$249.97Current Price $249.97(46% off)46% off.$465.00Comparable value $465.00(3)
NewAnthony VeerWilson Chukka Boot (Men)$139.97Current Price $139.97(40% off)40% off.$234.95Comparable value $234.95(1)
VANCE COAustin Cap Toe Chukka Boot - Wide Width (Men)$39.99Current Price $39.99(55% off)55% off.$89.99Comparable value $89.99(3)
TimberlandNewmarket Chukka Boot (Men)$58.48Current Price $58.48(61% off)61% off.$150.00Comparable value $150.00(6) 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)
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)
AriatSpitfire Leather Chukka Boot (Men)$69.97Current Price $69.97(50% off)50% off.$139.95Comparable value $139.95(50)
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
FryeBowery Chukka Boot (Men)$139.97Current Price $139.97(59% off)59% off.$348.00Comparable value $348.00(53) 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
Tommy HilfigerBage Chukka Boot (Men)$59.97Current Price $59.97(49% off)49% off.$119.00Comparable value $119.00(6)
VINTAGE FOUNDRYAnderson Casual Chukka Boot (Men)$69.97Current Price $69.97(60% off)60% off.$175.00Comparable value $175.00
NewVinceLafayette 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
TimberlandAttleboro Mid Chukka Boot (Men)$69.97Current Price $69.97(46% off)46% off.$130.00Comparable value $130.00(5)
MagnanniSuede Chukka Boot (Men)$239.97Current Price $239.97(51% off)51% off.$495.00Comparable value $495.00
Donald PlinerKingston Chukka Boot (Men)$149.97Current Price $149.97(53% off)53% off.$325.00Comparable value $325.00(2) Only a few left
Ben ShermanWhitby Chukka Boot (Men)$49.97Current Price $49.97(33% off)33% off.$75.00Comparable value $75.00(4)
Clarks®Wallaston Low Chukka Sneaker (Men)$84.97Current Price $84.97(22% off)22% off.$110.00Comparable value $110.00
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 $495.00New Markdown(35) Only a few left
Ben ShermanThames Chukka Boot (Men)$59.97Current Price $59.97(40% off)40% off.$100.00Comparable value $100.00
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
Tod'sIdeal Suede Chukka Boot (Men)$249.97Current Price $249.97(57% off)57% off.$595.00Comparable value $595.00