MagnanniEddison Chukka Boot (Men)$164.98Current Price $164.98(64% off)64% off.$465.00Comparable value $465.00New Markdown(3)
VITTORIO RUSSOWhitman Chukka Boot (Men)$84.98 – $89.98Current Price $84.98 to $89.98(Up to 62% off)Up to 62% off.$225.00Comparable value $225.00New Markdown(3)
Anthony VeerBushwick Chukka Boot (Men)$74.97Current Price $74.97(48% off)48% off.$145.99Comparable value $145.99(1)
Johnston & MurphyBoswell Chukka Boot (Men)$49.98Current Price $49.98(71% off)71% off.$175.00Comparable value $175.00New Markdown(17)
Dune LondonClaus Chukka Boot (Men)$89.97Current Price $89.97(52% off)52% off.$190.00Comparable value $190.00
BarbourReadhead Chukka Boot (Men)$109.97Current Price $109.97(50% off)50% off.$220.00Comparable value $220.00(2) Only a few left
UGG®Neumal Crafted Regenerate Water Resistant Chukka Boot (Men)$119.97Current Price $119.97(40% off)40% off.$200.00Comparable value $200.00(4) Only a few left
NewAnthony VeerGeorge Chukka Boot (Men)$99.97Current Price $99.97(39% off)39% off.$165.95Comparable value $165.95(1)
Donald PlinerKingston Chukka Boot (Men)$89.98 – $139.97Current Price $89.98 to $139.97(Up to 72% off select items)Up to 72% off select items.$325.00Comparable value $325.00New Markdown(3)
Allen EdmondsGrady Chukka Boot (Men)$119.98 – $149.98Current Price $119.98 to $149.98(Up to 78% off)Up to 78% off.$550.00Comparable value $550.00New Markdown
ECCOLite Hybrid Chukka Boot (Men)$79.97Current Price $79.97(42% off)42% off.$140.00Comparable value $140.00
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(4)
VinceLafayette Chukka Boot (Men)$89.99 – $109.99Current Price $89.99 to $109.99(Up to 74% off)Up to 74% off.$350.00Comparable value $350.00New Markdown
VANCE COStratton Chukka Boot (Men)$74.97Current Price $74.97(31% off)31% off.$109.99Comparable value $109.99(1)
TO BOOT NEW YORKJohnnie Chukka Boot (Men)$199.97Current Price $199.97(52% off)52% off.$425.00Comparable value $425.00
Bruno MagliMabelton Chukka Boot (Men)$179.97Current Price $179.97(57% off)57% off.$425.00Comparable value $425.00 Only a few left
Allen EdmondsDowning Chukka Boot (Men)$169.97Current Price $169.97(65% off)65% off.$495.00Comparable value $495.00(11)
VINTAGE FOUNDRYMarlow Chukka Boot (Men)$54.97Current Price $54.97(70% off)70% off.$185.00Comparable value $185.00
VinceDann Lugged Chukka Boot (Men)$99.99Current Price $99.99(73% off)73% off.$375.00Comparable value $375.00New Markdown(4)
TO BOOT NEW YORKHorace Chukka Boot (Men)$199.97Current Price $199.97(52% off)52% off.$425.00Comparable value $425.00
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
ALDOKenora Chukka Boot (Men)$59.97Current Price $59.97(53% off)53% off.$130.00Comparable value $130.00(3) Only a few left
MagnanniOslo Schore Chukka Boot (Men)$239.97Current Price $239.97(49% off)49% off.$475.00Comparable value $475.00(1)
Johnston & MurphyUpton Chukka (Men)$129.97Current Price $129.97(27% off)27% off.$179.00Comparable value $179.00
NewKenneth Cole ReactionVesto Chukka Boot (Men)$69.97Current Price $69.97(41% off)41% off.$119.00Comparable value $119.00(1)
Brooks BrothersClaremont Chukka (Men)$169.97Current Price $169.97(62% off)62% off.$449.00Comparable value $449.00(2)
Donald PlinerKingston Chukka Boot (Men)$149.97Current Price $149.97(53% off)53% off.$325.00Comparable value $325.00(2) Only a few left
Anthony VeerWilson Chukka Boot (Men)$139.97Current Price $139.97(40% off)40% off.$234.95Comparable value $234.95(1)
NewBruno MagliCat Walk Chukka Boot (Men)$159.97Current Price $159.97(54% off)54% off.$350.00Comparable value $350.00
NewPeter MillarTempest Chukka Boot (Men)$99.97Current Price $99.97(66% off)66% off.$295.00Comparable value $295.00 Only a few left
VinceJerome Chukka Boot (Men)$149.97Current Price $149.97(49% off)49% off.$295.00Comparable value $295.00
Tod'sIdeal Suede Chukka Boot (Men)$249.97Current Price $249.97(57% off)57% off.$595.00Comparable value $595.00(1)
Marc Joseph New YorkChicago Chukka Boot (Men)$79.97Current Price $79.97(58% off)58% off.$195.00Comparable value $195.00(1)
Tommy HilfigerHarbin Chukka Boot (Men)$24.99 – $39.99Current Price $24.99 to $39.99(Up to 79% off)Up to 79% off.$119.00Comparable value $119.00New Markdown(10)
Dockers®Esmond Chukka Boot (Men)$59.97Current Price $59.97(36% off)36% off.$95.00Comparable value $95.00(5)
NewSORELMadson II Waterproof Chukka Boot (Men)$99.97Current Price $99.97(47% off)47% off.$190.00Comparable value $190.00(30) Only a few left
NUNN BUSHDelton Plain Toe Chukka Boot (Men)$54.97Current Price $54.97(42% off)42% off.$95.00Comparable value $95.00
Clarks®Walpath Waterproof Chukka Boot (Men)$99.97Current Price $99.97(23% off)23% off.$130.00Comparable value $130.00(2) Only a few left
TimberlandAttleboro Mid Chukka Boot (Men)$69.97Current Price $69.97(46% off)46% off.$130.00Comparable value $130.00(5)
NewClarks®Torhill Lo Chukka Boot (Men)$69.97Current Price $69.97(46% off)46% off.$130.00Comparable value $130.00
Maison ForteDaytona Chukka Boot (Men)$109.97Current Price $109.97(43% off)43% off.$195.00Comparable value $195.00(3)
AriatSpitfire All Terrain Waterproof Chukka Boot (Men)$89.97Current Price $89.97(47% off)47% off.$169.95Comparable value $169.95(11)
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
NewUGG®Chukka Lug Boot (Men)$89.97Current Price $89.97(40% off)40% off.$150.00Comparable value $150.00 Only a few left
Thomas & VineKeegan Chukka Boot$79.97Current Price $79.97(23% off)23% off.$104.97Comparable value $104.97(2)
Donald PlinerSeya Chukka Boot (Men)$139.97Current Price $139.97(56% off)56% off.$325.00Comparable value $325.00(1)
La MilanoAcross II Cap Toe Chukka Boot (Men)$79.97Current Price $79.97(20% off)20% off.$99.99Comparable value $99.99
BørnTheo Chukka Boot (Men)$19.99 – $55.96Current Price $19.99 to $55.96(Up to 84% off)Up to 84% off.$130.00Comparable value $130.00New Markdown(13)
MagnanniSuede Chukka Boot (Men)$239.97Current Price $239.97(51% off)51% off.$495.00Comparable value $495.00
CARLOS SANTANACorazon Chukka Boot (Men)$109.97Current Price $109.97(38% off)38% off.$179.00Comparable value $179.00(1)
NewClarks®Wallabee Chukka (Men)$89.97Current Price $89.97(47% off)47% off.$170.00Comparable value $170.00
NUNN BUSHChase Plain Toe Chukka Boot - Wide Width Available (Men)$11.24 – $49.97Current Price $11.24 to $49.97(Up to 88% off select items)Up to 88% off select items.$95.00Comparable value $95.00New Markdown(14)
SantoniGregory Chukka Boot (Men)$344.96Current Price $344.96(61% off)61% off.$890.00Comparable value $890.00(1) Only a few left
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)
Cole HaanGrand Remix Chukka Boot (Men)$24.99 – $99.97Current Price $24.99 to $99.97(Up to 89% off select items)Up to 89% off select items.$220.00 – $230.00Comparable value $220.00 to $230.00New Markdown(15) 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)
Ben ShermanThames Chukka Boot (Men)$59.97Current Price $59.97(40% off)40% off.$100.00Comparable value $100.00 Only a few left
MagnanniLello Castagna Suede Boot (Men)$249.97Current Price $249.97(47% off)47% off.$475.00Comparable value $475.00
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)
RESERVE FOOTWEARZion Chukka Boot (Men)$39.97Current Price $39.97(50% off)50% off.$80.00Comparable value $80.00(3)
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
NUNN BUSHOzark II Chukka Boot (Men)$89.97Current Price $89.97(18% off)18% off.$110.00Comparable value $110.00(3)
Clarks®Wallaston Low Chukka Sneaker (Men)$84.97Current Price $84.97(22% off)22% off.$110.00Comparable value $110.00
Clarks®Wallaston Low Chukka Boot (Men)$84.97Current Price $84.97(22% off)22% off.$110.00Comparable value $110.00(2)
FERRAGAMOGiasone Ankle Chukka Boot (Men)$379.97Current Price $379.97(60% off)60% off.$950.00Comparable value $950.00
AriatSpitfire Leather Chukka Boot (Men)$69.97Current Price $69.97(50% off)50% off.$139.95Comparable value $139.95(53)
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
Dockers®Esmond Plain Toe Chukka Boot (Men)$59.97Current Price $59.97(29% off)29% off.$85.00Comparable value $85.00(10)
AriatSpitfire Leather Chukka Boot (Men)$59.97Current Price $59.97(53% off)53% off.$129.95Comparable value $129.95(331)
VANCE COAustin Cap Toe Chukka Boot - Wide Width (Men)$39.99 – $59.97Current Price $39.99 to $59.97(Up to 55% off select items)Up to 55% off select items.$89.99Comparable value $89.99(3)
NewClarks®Wallabee Genuine Calf Hair Chukka (Men)$99.97Current Price $99.97(44% off)44% off.$180.00Comparable value $180.00
NUNN BUSHOtto Chukka Boot - Wide Width Available (Men)$11.24 – $79.97Current Price $11.24 to $79.97(Up to 90% off select items)Up to 90% off select items.$110.00 – $120.00Comparable value $110.00 to $120.00New Markdown(14)