Johnston & MurphyBoswell Chukka Boot (Men)$89.97Current Price $89.97(48% off)48% off.$175.00Comparable value $175.00(10)
New!Cole HaanMorse GRANDFØAM Chukka Boot (Men)$129.97Current Price $129.97(40% off)40% off.$220.00Comparable value $220.00
Cole Haan2.Zerogrand Chukka Boot (Men)$99.97Current Price $99.97(70% off)70% off.$338.00Comparable value $338.00(395)
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(1)
New!Johnston & MurphyUpton Chukka Boot (Men)$69.97Current Price $69.97(58% off)58% off.$169.00Comparable value $169.00(18)
FlorsheimAzzano Plain Toe Chukka Boot (Men)$109.97Current Price $109.97(24% off)24% off.$145.00Comparable value $145.00
Tommy HilfigerHarbin Chukka Boot (Men)$59.97Current Price $59.97(49% off)49% off.$119.00Comparable value $119.00(7)
Cole HaanChamberlin Grand Chukka Boot (Men)$97.47 – $129.97Current Price $97.47 to $129.97(Up to 66% off select items)Up to 66% off select items.$290.00Comparable value $290.00(1)
Steve MaddenHemet Chukka Boot (Men)$74.97Current Price $74.97(42% off)42% off.$130.00Comparable value $130.00(3)
BørnTheo Chukka Boot (Men)$59.97 – $79.97Current Price $59.97 to $79.97(Up to 53% off select items)Up to 53% off select items.$130.00Comparable value $130.00(6)
ALDOJefry Chukka Boot (Men)$69.97Current Price $69.97(50% off)50% off.$140.00Comparable value $140.00
ALDOKenora Chukka Boot (Men)$59.97Current Price $59.97(53% off)53% off.$130.00Comparable value $130.00(1)
Johnston & MurphyCalder Chukka Boot (Men)$79.97Current Price $79.97(51% off)51% off.$165.00Comparable value $165.00(21)
VINTAGE FOUNDRYTreyton Chukka Boot (Men)$99.97Current Price $99.97(50% off)50% off.$200.00Comparable value $200.00(5)
Dune LondonClydell Chukka Boot (Men)$99.97Current Price $99.97(48% off)48% off.$195.00Comparable value $195.00
NUNN BUSHChase Plain Toe Chukka Boot - Wide Width Available (Men)$44.97 – $54.97Current Price $44.97 to $54.97(Up to 52% off)Up to 52% off.$90.00 – $95.00Comparable value $90.00 to $95.00(12)
Cole HaanGrand Remix Chukka Boot (Men)$99.97Current Price $99.97(Up to 56% off)Up to 56% off.$220.00 – $230.00Comparable value $220.00 to $230.00(14)
MagnanniEddison Chukka Boot (Men)$249.97Current Price $249.97(46% off)46% off.$465.00Comparable value $465.00(2)
Cole HaanGrand Atlantic Chukka Boot - Wide Width Available (Men)$74.97 – $99.97Current Price $74.97 to $99.97(Up to 62% off select items)Up to 62% off select items.$200.00Comparable value $200.00(38)
Donald PlinerKingston Chukka Boot (Men)$139.97Current Price $139.97(56% off)56% off.$325.00Comparable value $325.00(2)
New!Allen EdmondsDowning Chukka Boot (Men)$169.97Current Price $169.97(65% off)65% off.$495.00Comparable value $495.00(8)
VINTAGE FOUNDRYMarlow Chukka Boot (Men)$89.97Current Price $89.97(51% off)51% off.$185.00Comparable value $185.00
Allen EdmondsCarson Hybrid Chukka Boot (Men)$112.47 – $149.97Current Price $112.47 to $149.97(Up to 67% off select items)Up to 67% off select items.$345.00Comparable value $345.00(24)
BarbourReadhead Chukka Boot (Men)$109.97 – $119.97Current Price $109.97 to $119.97(Up to 50% off)Up to 50% off.$220.00Comparable value $220.00(2)
BørnSeth Chukka Boot (Men)$89.97Current Price $89.97(35% off)35% off.$140.00Comparable value $140.00(7)
TO BOOT NEW YORKJohnnie Chukka Boot (Men)$199.97Current Price $199.97(52% off)52% off.$425.00Comparable value $425.00
Hawker RyeGarner Chukka Boot (Men)$39.97Current Price $39.97(55% off)55% off.$89.00Comparable value $89.00
EastlandJack Chukka Boot (Men)$89.97Current Price $89.97(28% off)28% off.$125.00Comparable value $125.00(1)
FryeBowery Chukka Boot (Men)$189.97Current Price $189.97(45% off)45% off.$348.00Comparable value $348.00(49)
New!TO BOOT NEW YORKHorace Chukka Boot (Men)$199.97Current Price $199.97(52% off)52% off.$425.00Comparable value $425.00
Hawker RyeBreck Chukka Boot (Men)$39.97Current Price $39.97(55% off)55% off.$89.00Comparable value $89.00
Tommy HilfigerBage Chukka Boot (Men)$59.97Current Price $59.97(49% off)49% off.$119.00Comparable value $119.00(6)
NUNN BUSHOzark II Chukka Boot (Men)$89.97Current Price $89.97(18% off)18% off.$110.00Comparable value $110.00(3)
Dockers®Dee Chukka Boot (Men)$39.97Current Price $39.97(57% off)57% off.$95.00Comparable value $95.00
BørnLincoln Chukka (Men)$89.97Current Price $89.97(41% off)41% off.$155.00Comparable value $155.00(4)
FryeBowery Chukka Boot (Men)$142.47 – $189.97Current Price $142.47 to $189.97(Up to 59% off select items)Up to 59% off select items.$348.00Comparable value $348.00(49)
Dockers®Esmond Plain Toe Chukka Boot (Men)$69.97Current Price $69.97(17% off)17% off.$85.00Comparable value $85.00(5)
Ben ShermanWhitby Chukka Boot (Men)$54.97Current Price $54.97(35% off)35% off.$85.00Comparable value $85.00(3)
Tommy HilfigerBlaze Lace Cap Toe Boot (Men)$59.97Current Price $59.97(49% off)49% off.$119.00Comparable value $119.00
NUNN BUSHOtto Chukka Boot - Wide Width Available (Men)$44.97 – $79.97Current Price $44.97 to $79.97(Up to 52% off)Up to 52% off.$95.00 – $110.00Comparable value $95.00 to $110.00(13)
Clarks®Radcliff Plain Toe Chukka Boot (Men)$89.97Current Price $89.97(25% off)25% off.$120.00Comparable value $120.00(1)
Allen EdmondsDonovan Chukka Boot (Men)$199.97Current Price $199.97(59% off)59% off.$495.00Comparable value $495.00
SperryTOP-SIDER Newman Water Resistant Chukka Boot (Men)$39.97Current Price $39.97(60% off)60% off.$100.00Comparable value $100.00(2)Only a few left
NordstromPayton Mini Lug Pebbled Leather Chukka Boot (Men)$69.97Current Price $69.97(46% off)46% off.$129.95Comparable value $129.95(12)Only a few left
Deer StagsGarfield Plain Toe Chukka Boot (Men)$64.97Current Price $64.97(35% off)35% off.$100.00Comparable value $100.00
NUNN BUSHDelton Plain Toe Chukka Boot (Men)$54.97Current Price $54.97(42% off)42% off.$95.00Comparable value $95.00
VinceDann Lugged Chukka Boot (Men)$159.97Current Price $159.97(57% off)57% off.$375.00Comparable value $375.00(2)
Bruno MagliMabelton Chukka Boot (Men)$179.97Current Price $179.97(57% off)57% off.$425.00Comparable value $425.00
JOHNSTON & MURPHY COLLECTIONWelch Chukka Boot (Men)$127.47Current Price $127.47(51% off)51% off.$265.00Comparable value $265.00(9)
CARLOS SANTANACorazon Chukka Boot (Men)$119.97Current Price $119.97(24% off)24% off.$158.99Comparable value $158.99
Dockers®Esmond Chukka Boot (Men)$59.97Current Price $59.97(36% off)36% off.$95.00Comparable value $95.00
New!BarbourTucker Chukka Boot (Men)$109.97Current Price $109.97(48% off)48% off.$215.00Comparable value $215.00
VANCE COStratton Chukka Boot (Men)$74.97Current Price $74.97(31% off)31% off.$109.99Comparable value $109.99
Allen EdmondsHamilton Wingtip Waterproof Chukka Boot (Men)$199.97Current Price $199.97(59% off)59% off.$495.00Comparable value $495.00(44)Only a few left
New!EastlandJack Chukka Boot (Men)$99.97Current Price $99.97(20% off)20% off.$125.00Comparable value $125.00(1)
VINTAGE FOUNDRYMilton Chukka Boot (Men)$109.97Current Price $109.97(38% off)38% off.$180.00Comparable value $180.00(3)
BørnEli Suede Chukka Boot (Men)$89.97Current Price $89.97(30% off)30% off.$130.00Comparable value $130.00(1)
Clarks®Wallaston Chukka Boot (Men)$79.97Current Price $79.97(33% off)33% off.$120.00Comparable value $120.00(1)
Johnston & MurphyHenson XC4 Waterproof Chukka Boot (Men)$99.97 – $109.97Current Price $99.97 to $109.97(Up to 49% off)Up to 49% off.$199.00Comparable value $199.00(18)
NUNN BUSHCircuit Plain Toe Chukka Boot - Wide Width Available (Men)$54.97Current Price $54.97(38% off)38% off.$90.00Comparable value $90.00(17)
Allen EdmondsChandler Lug Chukka Boot (Men)$309.97Current Price $309.97(37% off)37% off.$495.00Comparable value $495.00(10)
VANCE COVaughn Lace-Up Chukka Boot (Men)$34.97Current Price $34.97(70% off)70% off.$119.99Comparable value $119.99(1)Only a few left
Clarks®Steadwell Plain Toe Chukka Boot (Men)$79.97Current Price $79.97(27% off)27% off.$110.00Comparable value $110.00
New!La MilanoAcross II Cap Toe Chukka Boot (Men)$79.97Current Price $79.97(20% off)20% off.$99.99Comparable value $99.99
VANCE COJimmy Plain Toe Vegan Leather Chukka Boot (Men)$39.99Current Price $39.99(63% off)63% off.$109.99Comparable value $109.99
BørnThomson Chukka Boot (Men)$89.97Current Price $89.97(30% off)30% off.$130.00Comparable value $130.00(25)
New!Allen EdmondsCaden Lug Sole Chukka Boot (Men)$199.97 – $249.97Current Price $199.97 to $249.97(Up to 63% off)Up to 63% off.$550.00Comparable value $550.00
Allen EdmondsChandler Lug Chukka Boot (Men)$199.97Current Price $199.97(59% off)59% off.$495.00Comparable value $495.00(34)
TO BOOT NEW YORKRosemead Chukka Boot (Men)$189.97Current Price $189.97(52% off)52% off.$399.00Comparable value $399.00
SPERRY TOP-SIDER®Authentic Original Chukka Boot (Men)$49.97Current Price $49.97(61% off)61% off.$130.00Comparable value $130.00(4)
EastlandSeth Memory Foam Chukka Boot (Men)$44.97Current Price $44.97(50% off)50% off.$90.00Comparable value $90.00(1)
NUNN BUSHDenali Waterproof Plain Toe Boot - Wide Width Available$99.97Current Price $99.97(16% off)16% off.$120.00Comparable value $120.00(1)