New!Bruno MagliMabelton Chukka Boot (Men)$179.97Current Price $179.97(57% off)57% off.$425.00Comparable value $425.00
New!AllSaintsSkiff Chukka Boot (Men)$174.97Current Price $174.97(41% off)41% off.$299.00Comparable value $299.00(2)
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)
VinceDann Lugged Chukka Boot (Men)$159.97Current Price $159.97(57% off)57% off.$375.00Comparable value $375.00(2)
ALDOKenora Chukka Boot (Men)$59.97Current Price $59.97(53% off)53% off.$130.00Comparable value $130.00
New!Donald PlinerSeya Chukka Boot (Men)$139.97Current Price $139.97(56% off)56% off.$325.00Comparable value $325.00
New!TO BOOT NEW YORKJohnnie Chukka Boot (Men)$199.97Current Price $199.97(52% off)52% off.$425.00Comparable value $425.00
CARLOS SANTANACorazon Chukka Boot (Men)$119.97Current Price $119.97(24% off)24% off.$158.99Comparable value $158.99
Steve MaddenHemet Chukka Boot (Men)$74.97Current Price $74.97(42% off)42% off.$130.00Comparable value $130.00(3)
TO BOOT NEW YORKVinny Chukka Boot (Men)$199.97Current Price $199.97(52% off)52% off.$425.00Comparable value $425.00(1)
Clarks®Wallaston Chukka Boot (Men)$79.97Current Price $79.97(33% off)33% off.$120.00Comparable value $120.00(1)
New!Cole HaanMorse GRANDFØAM Chukka Boot (Men)$109.97Current Price $109.97(51% off)51% off.$228.00Comparable value $228.00
BOSSClay Chukka Sneaker Boot (Men)$114.97Current Price $114.97(50% off)50% off.$230.00Comparable value $230.00
KARL LAGERFELD PARISSuede Lug Chukka Boot (Men)$69.97Current Price $69.97(68% off)68% off.$225.00Comparable value $225.00(32)
New!Hawker RyeBreck Chukka Boot (Men)$39.97Current Price $39.97(55% off)55% off.$89.00Comparable value $89.00
Clarks®Shepton Chukka Boot (Men)$74.97Current Price $74.97(31% off)31% off.$110.00Comparable value $110.00
New!TO BOOT NEW YORKHorace Chukka Boot (Men)$199.97Current Price $199.97(52% off)52% off.$425.00Comparable value $425.00
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
Black Friday DealVINTAGE FOUNDRYTreyton Chukka Boot (Men)$74.99Current Price $74.99(62% off)62% off.$200.00Comparable value $200.00(5)
New!BarbourTucker Chukka Boot (Men)$109.97Current Price $109.97(48% off)48% off.$215.00Comparable value $215.00
Allen EdmondsGraham Chukka Boot (Men)$199.97Current Price $199.97(59% off)59% off.$495.00Comparable value $495.00(16)
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 RyeGarner Chukka Boot (Men)$39.97Current Price $39.97(55% off)55% off.$89.00Comparable value $89.00
New!ALDOJefry Chukka Boot (Men)$69.97Current Price $69.97(50% off)50% off.$140.00Comparable value $140.00
FryeBowery Chukka Boot (Men)$189.97Current Price $189.97(45% off)45% off.$348.00Comparable value $348.00(49)
Cole Haan2.Zerogrand Chukka Boot (Men)$99.97Current Price $99.97(70% off)70% off.$338.00Comparable value $338.00(389)
Tommy HilfigerHarbin Chukka Boot (Men)$59.97Current Price $59.97(49% off)49% off.$119.00Comparable value $119.00(7)
Donald PlinerKingston Chukka Boot (Men)$139.97Current Price $139.97(56% off)56% off.$325.00Comparable value $325.00(2)
VinceJune Chukka Boot (Men)$149.97Current Price $149.97(60% off)60% off.$375.00Comparable value $375.00(1)
BørnThomson Chukka Boot (Men)$89.97Current Price $89.97(30% off)30% off.$130.00Comparable value $130.00(25)
Black Friday DealUGG®Burleigh Chukka (Men)$89.97Current Price $89.97(43% off)43% off.$160.00Comparable value $160.00(12)
New!Dune LondonClydell Chukka Boot (Men)$99.97Current Price $99.97(48% off)48% off.$195.00Comparable value $195.00
Johnston & MurphyBoswell Chukka Boot (Men)$89.97Current Price $89.97(48% off)48% off.$175.00Comparable value $175.00(5)
MagnanniEddison Chukka Boot (Men)$249.97Current Price $249.97(46% off)46% off.$465.00Comparable value $465.00(2)
New!BørnEli Suede Chukka Boot (Men)$89.97Current Price $89.97(30% off)30% off.$130.00Comparable value $130.00(1)
RESERVE FOOTWEARKeon Chukka Boot (Men)$54.97Current Price $54.97(54% off)54% off.$120.00Comparable value $120.00(5)
BørnSeth Chukka Boot (Men)$89.97Current Price $89.97(35% off)35% off.$140.00Comparable value $140.00(7)
TO BOOT NEW YORKRosemead Chukka Boot (Men)$189.97Current Price $189.97(52% off)52% off.$399.00Comparable value $399.00
VinceJune Chukka Boot (Men)$149.97Current Price $149.97(60% off)60% off.$375.00Comparable value $375.00
Black Friday DealUGG®The UGG Lug Waterproof Chukka Boot (Men)$79.97Current Price $79.97(38% off)38% off.$130.00Comparable value $130.00Only a few left
New!FryeBowery Chukka Boot (Men)$189.97Current Price $189.97(45% off)45% off.$348.00Comparable value $348.00(49)
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 EdmondsChandler Lug Chukka Boot (Men)$199.97Current Price $199.97(59% off)59% off.$495.00Comparable value $495.00(34)
Allen EdmondsDonovan Chukka Boot (Men)$199.97Current Price $199.97(59% off)59% off.$495.00Comparable value $495.00
Maison ForteSawyer Hybrid Chukka Boot (Men)$109.97Current Price $109.97(40% off)40% off.$185.00Comparable value $185.00(7)
TO BOOT NEW YORKVersailles Chukka Boot (Men)$269.97Current Price $269.97(40% off)40% off.$450.00Comparable value $450.00(8)
VINTAGE FOUNDRYMarlow Chukka Boot (Men)$89.97Current Price $89.97(51% off)51% off.$185.00Comparable value $185.00
New!Cole HaanChamberlin Grand Chukka Boot (Men)$129.97Current Price $129.97(55% off)55% off.$290.00Comparable value $290.00(1)
VANCE COStratton Chukka Boot (Men)$74.97Current Price $74.97(31% off)31% off.$109.99Comparable value $109.99
BørnTheo Chukka Boot (Men)$79.97Current Price $79.97(38% off)38% off.$130.00Comparable value $130.00(5)
The North FaceNSE Chukka Boot (Men)$59.97Current Price $59.97(44% off)44% off.$109.00Comparable value $109.00
Allen EdmondsHarris Chukka Boot (Men)$199.97Current Price $199.97(49% off)49% off.$395.00Comparable value $395.00(14)
RESERVE FOOTWEARDeegan Leather Chukka Boot (Men)$89.97Current Price $89.97(33% off)33% off.$135.00Comparable value $135.00(3)
Cole HaanGrand Atlantic Chukka Boot - Wide Width Available (Men)$99.97Current Price $99.97(50% off)50% off.$200.00Comparable value $200.00(38)
Tod'sIdeal Suede Chukka Boot (Men)$249.97Current Price $249.97(57% off)57% off.$595.00Comparable value $595.00Only a few left
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)
Tommy HilfigerBlaze Lace Cap Toe Boot (Men)$59.97Current Price $59.97(49% off)49% off.$119.00Comparable value $119.00
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)
VINTAGE FOUNDRYMilton Chukka Boot (Men)$109.97Current Price $109.97(38% off)38% off.$180.00Comparable value $180.00(3)
Bruno MagliPrimo High Top Chukka Boot (Men)$149.97Current Price $149.97(57% off)57% off.$350.00Comparable value $350.00(4)
New!Johnston & MurphyUpton Chukka Boot (Men)$69.97Current Price $69.97(58% off)58% off.$169.00Comparable value $169.00(17)
Maison ForteDaytona Chukka Boot (Men)$109.97Current Price $109.97(43% off)43% off.$195.00Comparable value $195.00(2)Only a few left
Ben ShermanThames Chukka Boot (Men)$74.97Current Price $74.97(34% off)34% off.$115.00Comparable value $115.00
New!FryeBowery Chukka (Men)$189.97Current Price $189.97(45% off)45% off.$348.00Comparable value $348.00(25)
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)
FERRAGAMOGiasone Ankle Chukka Boot (Men)$379.97Current Price $379.97(60% off)60% off.$950.00Comparable value $950.00
Allen EdmondsHamilton Wingtip Waterproof Chukka Boot (Men)$199.97Current Price $199.97(59% off)59% off.$495.00Comparable value $495.00(43)
JOHNSTON & MURPHY COLLECTIONMarlow Laceless Chukka Boot (Men)$79.97Current Price $79.97(69% off)69% off.$265.00Comparable value $265.00(2)
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)
Anthony VeerBushwick Chukka Boot (Men)$114.97Current Price $114.97(21% off)21% off.$145.95Comparable value $145.95(1)Only a few left
Black Friday DealUGG®Neumel Chukka Boot (Men)$79.99Current Price $79.99(46% off)46% off.$150.00Comparable value $150.00(457)Only a few left
FlorsheimAzzano Plain Toe Chukka Boot (Men)$109.97Current Price $109.97(24% off)24% off.$145.00Comparable value $145.00