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)
Deer StagsGarfield Plain Toe Chukka Boot (Men)$64.97Current Price $64.97(35% off)35% off.$100.00Comparable value $100.00
RESERVE FOOTWEARKeon Chukka Boot (Men)$54.97Current Price $54.97(54% off)54% off.$120.00Comparable value $120.00(5)
New!SPERRY TOP-SIDER®Authentic Original Chukka Boot (Men)$49.97Current Price $49.97(61% off)61% off.$130.00Comparable value $130.00(4)
Anthony VeerWilson Chukka Boot (Men)$139.97Current Price $139.97(40% off)40% off.$234.95Comparable value $234.95(1)Only a few left
Dockers®Dee Chukka Boot (Men)$39.97Current Price $39.97(57% off)57% off.$95.00Comparable value $95.00
BarbourHobart Chukka Boot (Men)$109.97Current Price $109.97(48% off)48% off.$215.00Comparable value $215.00Only a few left
NUNN BUSHOtto Plain Toe Chukka Boot - Wide Width Available (Men)$69.97Current Price $69.97(36% off)36% off.$110.00Comparable value $110.00(7)
The North FaceNSE Chukka Boot (Men)$59.97Current Price $59.97(44% off)44% off.$109.00Comparable value $109.00
Anthony VeerBushwick Chukka Boot (Men)$114.97Current Price $114.97(21% off)21% off.$145.95Comparable value $145.95(1)Only a few left
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(16)
Maison ForteSawyer Hybrid Chukka Boot (Men)$109.97Current Price $109.97(40% off)40% off.$185.00Comparable value $185.00(7)
Tod'sIdeal Suede Chukka Boot (Men)$249.97Current Price $249.97(57% off)57% off.$595.00Comparable value $595.00Only a few left
Maison ForteDaytona Chukka Boot (Men)$109.97Current Price $109.97(43% off)43% off.$195.00Comparable value $195.00(2)Only a few left
JOHNSTON & MURPHY COLLECTIONMarlow Laceless Chukka Boot (Men)$79.97Current Price $79.97(69% off)69% off.$265.00Comparable value $265.00(2)
EastlandPatterson Cap Toe Chukka Boot (Men)$59.97Current Price $59.97(33% off)33% off.$90.00Comparable value $90.00
EastlandSeth Memory Foam Chukka Boot (Men)$59.97Current Price $59.97(33% off)33% off.$90.00Comparable value $90.00(1)
NUNN BUSHOtto Chukka Boot - Wide Width Available (Men)$44.97 – $74.97Current Price $44.97 to $74.97(Up to 52% off)Up to 52% off.$95.00Comparable value $95.00(11)
TimberlandWestmore Chukka Boot (Men)$69.97Current Price $69.97(36% off)36% off.$110.00Comparable value $110.00
Bruno MagliPrimo High Top Chukka Boot (Men)$149.97Current Price $149.97(57% off)57% off.$350.00Comparable value $350.00(4)
Johnston & MurphyBrody Chukka Boot (Men)$109.97Current Price $109.97(33% off)33% off.$165.00Comparable value $165.00(25)Only a few left
Brooks BrothersClaremont Chukka (Men)$269.97Current Price $269.97(39% off)39% off.$449.00Comparable value $449.00Only a few left
TimberlandNewmarket Chukka Boot (Men)$89.97Current Price $89.97(40% off)40% off.$150.00Comparable value $150.00(5)
New!BørnLincoln Chukka (Men)$89.97Current Price $89.97(41% off)41% off.$155.00Comparable value $155.00(3)
Allen EdmondsChandler Lug Chukka Boot (Men)$309.97Current Price $309.97(37% off)37% off.$495.00Comparable value $495.00(9)
New!FERRAGAMOGiasone Ankle Chukka Boot (Men)$379.97Current Price $379.97(60% off)60% off.$950.00Comparable value $950.00
RESERVE FOOTWEARPositron Lug Sole Leather Chukka Boot (Men)$84.97Current Price $84.97(34% off)34% off.$129.00Comparable value $129.00(1)Only a few left
RESERVE FOOTWEARZion Chukka Boot (Men)$39.97Current Price $39.97(50% off)50% off.$80.00Comparable value $80.00(2)
New!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)
Black Friday DealUGG®Neumel Boot (Men)$79.99Current Price $79.99(46% off)46% off.$150.00Comparable value $150.00(6)
Black Friday DealDockers®Esmond Chukka Boot (Men)$54.99Current Price $54.99(42% off)42% off.$95.00Comparable value $95.00
UGG®Neumal Crafted Regenerate Water Resistant Chukka Boot (Men)$99.97Current Price $99.97(50% off)50% off.$200.00Comparable value $200.00(4)
New!TimberlandAttleboro Mid Chukka Boot (Men)$69.97Current Price $69.97(46% off)46% off.$130.00Comparable value $130.00(5)
New!SperryColdbay Chukka Boot (Men)$39.97Current Price $39.97(66% off)66% off.$120.00Comparable value $120.00
New!SKECHERSx John Deere Segment 2.0 Waterproof Chelsea Boot (Men)$59.97Current Price $59.97(53% off)53% off.$128.00Comparable value $128.00(4)
ROANTimothy Suede Chukka Boot$69.97Current Price $69.97(29% off)29% off.$99.00Comparable value $99.00(2)
Black Friday DealUGG®Neumel Chukka Boot (Men)$79.99Current Price $79.99(46% off)46% off.$150.00Comparable value $150.00(457)
Black Friday DealUGG®Neumel Water Resistant High Top Chukka Boot (Men)$89.99Current Price $89.99(43% off)43% off.$160.00Comparable value $160.00(8)Only a few left
RESERVE FOOTWEARBaryon Leather Chukka Boot (Men)$79.97Current Price $79.97(32% off)32% off.$119.00Comparable value $119.00Only a few left
VANCE COAustin Cap Toe Chukka Boot - Wide Width (Men)$39.99Current Price $39.99(55% off)55% off.$89.99Comparable value $89.99(2)
VINTAGE FOUNDRYParker Wingtip Boot (Men)$89.97Current Price $89.97(39% off)39% off.$149.00Comparable value $149.00(4)
RESERVE FOOTWEARFritz Suede Chukka Boot (Men)$89.97Current Price $89.97(40% off)40% off.$150.00Comparable value $150.00Only a few left
VANCE COFranco Plain Toe Chukka Boot - Wide Width (Men)$34.97Current Price $34.97(58% off)58% off.$84.99Comparable value $84.99(2)
Black Friday DealUGG®Hayden Chukka Boot (Men)$79.99Current Price $79.99(46% off)46% off.$150.00Comparable value $150.00(5)
New!AriatSpitfire Leather Chukka Boot (Men)$69.97Current Price $69.97(50% off)50% off.$139.95Comparable value $139.95(41)
Black Friday DealDockers®Calgary Chukka Boot (Men)$59.99Current Price $59.99(36% off)36% off.$95.00Comparable value $95.00
Deer StagsBangor Chukka Boot$54.97Current Price $54.97(45% off)45% off.$100.00Comparable value $100.00
VANCE COVaughn Lace-Up Chukka Boot (Men)$34.97Current Price $34.97(70% off)70% off.$119.99Comparable value $119.99Only a few left
Dr. MartensPatchwork Church Chukka Boot (Men)$119.97Current Price $119.97(40% off)40% off.$200.00Comparable value $200.00(3)
RESERVE FOOTWEARKeither Chukka Boot (Men)$39.97Current Price $39.97(55% off)55% off.$90.00Comparable value $90.00(1)Only a few left
Hey DudeWally Mid Chukka Boot (Men)$39.97Current Price $39.97(42% off)42% off.$69.99Comparable value $69.99(12)
UGG®Neumel Shaggy Suede Chukka Boot (Men)$89.97 – $94.97Current Price $89.97 to $94.97(Up to 40% off)Up to 40% off.$150.00Comparable value $150.00(1)