New!Bruno MagliMabelton Chukka Boot (Men)$179.97Current Price $179.97(57% off)57% off.$425.00Comparable value $425.00
VinceDann Lugged Chukka Boot (Men)$159.97Current Price $159.97(57% off)57% off.$375.00Comparable value $375.00(2)
New!Dune LondonClydell Chukka Boot (Men)$99.97Current Price $99.97(48% off)48% off.$195.00Comparable value $195.00
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(1)
Tommy HilfigerHarbin Chukka Boot (Men)$59.97Current Price $59.97(49% off)49% off.$119.00Comparable value $119.00(7)
New!BørnEli Suede Chukka Boot (Men)$89.97Current Price $89.97(30% off)30% off.$130.00Comparable value $130.00(1)
New!TO BOOT NEW YORKHorace Chukka Boot (Men)$199.97Current Price $199.97(52% off)52% off.$425.00Comparable value $425.00
Johnston & MurphyBoswell Chukka Boot (Men)$89.97Current Price $89.97(48% off)48% off.$175.00Comparable value $175.00(5)
Clarks®Wallaston Chukka Boot (Men)$79.97Current Price $79.97(33% off)33% off.$120.00Comparable value $120.00(1)
MagnanniEddison Chukka Boot (Men)$249.97Current Price $249.97(46% off)46% off.$465.00Comparable value $465.00(2)
Steve MaddenHemet Chukka Boot (Men)$74.97Current Price $74.97(42% off)42% off.$130.00Comparable value $130.00(3)
KARL LAGERFELD PARISSuede Lug Chukka Boot (Men)$69.97Current Price $69.97(68% off)68% off.$225.00Comparable value $225.00(32)
BørnTheo Chukka Boot (Men)$79.97Current Price $79.97(38% off)38% off.$130.00Comparable value $130.00(5)
New!TO BOOT NEW YORKJohnnie Chukka Boot (Men)$199.97Current Price $199.97(52% off)52% off.$425.00Comparable value $425.00
New!BarbourTucker Chukka Boot (Men)$109.97Current Price $109.97(48% off)48% off.$215.00Comparable value $215.00
New!Cole HaanMorse GRANDFØAM Chukka Boot (Men)$109.97Current Price $109.97(51% off)51% off.$228.00Comparable value $228.00
Black Friday DealVINTAGE FOUNDRYTreyton Chukka Boot (Men)$74.99Current Price $74.99(62% off)62% off.$200.00Comparable value $200.00(5)
New!AllSaintsSkiff Chukka Boot (Men)$174.97Current Price $174.97(41% off)41% off.$299.00Comparable value $299.00(2)
FryeBowery Chukka Boot (Men)$189.97Current Price $189.97(45% off)45% off.$348.00Comparable value $348.00(49)
Donald PlinerKingston Chukka Boot (Men)$139.97Current Price $139.97(56% off)56% off.$325.00Comparable value $325.00(2)
FlorsheimAzzano Plain Toe Chukka Boot (Men)$109.97Current Price $109.97(24% off)24% off.$145.00Comparable value $145.00
BørnThomson Chukka Boot (Men)$89.97Current Price $89.97(30% off)30% off.$130.00Comparable value $130.00(25)
New!FryeBowery Chukka Boot (Men)$189.97Current Price $189.97(45% off)45% off.$348.00Comparable value $348.00(49)
TO BOOT NEW YORKRosemead Chukka Boot (Men)$189.97Current Price $189.97(52% off)52% off.$399.00Comparable value $399.00
ALDOKenora Chukka Boot (Men)$59.97Current Price $59.97(53% off)53% off.$130.00Comparable value $130.00
Allen EdmondsDonovan Chukka Boot (Men)$199.97Current Price $199.97(59% off)59% off.$495.00Comparable value $495.00
Ben ShermanThames Chukka Boot (Men)$74.97Current Price $74.97(34% off)34% off.$115.00Comparable value $115.00
NUNN BUSHOzark II Chukka Boot (Men)$94.97Current Price $94.97(13% off)13% off.$110.00Comparable value $110.00(3)
Clarks®Shepton Chukka Boot (Men)$74.97Current Price $74.97(31% off)31% off.$110.00Comparable value $110.00
New!Johnston & MurphyUpton Chukka Boot (Men)$69.97Current Price $69.97(58% off)58% off.$169.00Comparable value $169.00(17)
Cole Haan2.Zerogrand Chukka Boot (Men)$99.97Current Price $99.97(70% off)70% off.$338.00Comparable value $338.00(389)
TO BOOT NEW YORKVinny Chukka Boot (Men)$199.97Current Price $199.97(52% off)52% off.$425.00Comparable value $425.00(1)
Allen EdmondsGraham Chukka Boot (Men)$199.97Current Price $199.97(59% off)59% off.$495.00Comparable value $495.00(16)
VINTAGE FOUNDRYMarlow Chukka Boot (Men)$89.97Current Price $89.97(51% off)51% off.$185.00Comparable value $185.00
New!FryeBowery Chukka (Men)$189.97Current Price $189.97(45% off)45% off.$348.00Comparable value $348.00(25)
CARLOS SANTANACorazon Chukka Boot (Men)$119.97Current Price $119.97(24% off)24% off.$158.99Comparable value $158.99
New!Donald PlinerSeya Chukka Boot (Men)$139.97Current Price $139.97(56% off)56% off.$325.00Comparable value $325.00
BørnSeth Chukka Boot (Men)$89.97Current Price $89.97(35% off)35% off.$140.00Comparable value $140.00(7)
Allen EdmondsCarson Hybrid Chukka Boot (Men)$149.97 – $159.97Current Price $149.97 to $159.97(Up to 56% off)Up to 56% off.$345.00Comparable value $345.00(24)
New!ALDOJefry Chukka Boot (Men)$69.97Current Price $69.97(50% off)50% off.$140.00Comparable value $140.00
New!Cole HaanChamberlin Grand Chukka Boot (Men)$129.97Current Price $129.97(55% off)55% off.$290.00Comparable value $290.00(1)
Johnston & MurphyCalder Chukka Boot (Men)$79.97Current Price $79.97(51% off)51% off.$165.00Comparable value $165.00(18)
Tommy HilfigerBlaze Lace Cap Toe Boot (Men)$59.97Current Price $59.97(49% off)49% off.$119.00Comparable value $119.00
Allen EdmondsHamilton Wingtip Waterproof Chukka Boot (Men)$199.97Current Price $199.97(59% off)59% off.$495.00Comparable value $495.00(43)
VINTAGE FOUNDRYAnderson Casual Chukka Boot (Men)$99.97 – $119.97Current Price $99.97 to $119.97(Up to 42% off)Up to 42% off.$175.00Comparable value $175.00
Allen EdmondsChandler Lug Chukka Boot (Men)$199.97Current Price $199.97(59% off)59% off.$495.00Comparable value $495.00(34)
Clarks®Radcliff Plain Toe Chukka Boot (Men)$89.97Current Price $89.97(25% off)25% off.$120.00Comparable value $120.00(1)
NUNN BUSHCircuit Plain Toe Chukka Boot - Wide Width Available (Men)$54.97Current Price $54.97(38% off)38% off.$90.00Comparable value $90.00(16)
VinceJune Chukka Boot (Men)$149.97Current Price $149.97(60% off)60% off.$375.00Comparable value $375.00(1)
New!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(12)
Allen EdmondsHarris Chukka Boot (Men)$199.97Current Price $199.97(49% off)49% off.$395.00Comparable value $395.00(14)
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(11)
TO BOOT NEW YORKVersailles Chukka Boot (Men)$269.97Current Price $269.97(40% off)40% off.$450.00Comparable value $450.00(8)
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
New!Hawker RyeBreck Chukka Boot (Men)$39.97Current Price $39.97(55% off)55% off.$89.00Comparable value $89.00
VINTAGE FOUNDRYMilton Chukka Boot (Men)$109.97Current Price $109.97(38% off)38% off.$180.00Comparable value $180.00(3)
Clarks®Steadwell Plain Toe Chukka Boot (Men)$79.97Current Price $79.97(27% off)27% off.$110.00Comparable value $110.00
VANCE COStratton Chukka Boot (Men)$74.97Current Price $74.97(31% off)31% off.$109.99Comparable value $109.99
BOSSClay Chukka Sneaker Boot (Men)$114.97Current Price $114.97(50% off)50% off.$230.00Comparable value $230.00
RESERVE FOOTWEARDeegan Leather Chukka Boot (Men)$89.97Current Price $89.97(33% off)33% off.$135.00Comparable value $135.00(3)
NUNN BUSHDelton Plain Toe Chukka Boot (Men)$54.97Current Price $54.97(42% off)42% off.$95.00Comparable value $95.00
Ben ShermanWhitby Chukka Boot (Men)$54.97Current Price $54.97(Up to 42% off)Up to 42% off.$85.00 – $95.00Comparable value $85.00 to $95.00(3)
VinceJune Chukka Boot (Men)$149.97Current Price $149.97(60% off)60% off.$375.00Comparable value $375.00
Tommy HilfigerBage Chukka Boot (Men)$59.97 – $64.97Current Price $59.97 to $64.97(Up to 49% off)Up to 49% off.$119.00Comparable value $119.00(6)
New!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(123)
JOHNSTON & MURPHY COLLECTIONWelch Chukka Boot (Men)$169.97Current Price $169.97(35% off)35% off.$265.00Comparable value $265.00(9)
Cole HaanGrand Atlantic Chukka Boot - Wide Width Available (Men)$99.97Current Price $99.97(50% off)50% off.$200.00Comparable value $200.00(38)
BarbourBoulder Chukka Boot (Men)$119.97Current Price $119.97(47% off)47% off.$230.00Comparable value $230.00(1)
Clarks®Walpath Waterproof Chukka Boot (Men)$99.97Current Price $99.97(23% off)23% off.$130.00Comparable value $130.00
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)
Black Friday DealDockers®Esmond Plain Toe Chukka Boot (Men)$39.97 – $54.99Current Price $39.97 to $54.99(Up to 57% off)Up to 57% off.$85.00 – $95.00Comparable value $85.00 to $95.00(5)
NUNN BUSHDenali Waterproof Plain Toe Boot - Wide Width Available$99.97Current Price $99.97(16% off)16% off.$120.00Comparable value $120.00(1)