UGG®Burleigh Chukka (Men)$89.97Current Price $89.97(43% off)43% off.$160.00Comparable value $160.00(19)Only a few left
New!Thomas & VineKeegan Chukka Boot$79.97Current Price $79.97(23% off)23% off.$104.97Comparable value $104.97(2)
EastlandSeth Memory Foam Chukka Boot (Men)$44.96Current Price $44.96(50% off)50% off.$90.00Comparable value $90.00(1)
NUNN BUSHDelton Plain Toe Chukka Boot (Men)$54.97Current Price $54.97(42% off)42% off.$95.00Comparable value $95.00
AriatSpitfire All Terrain Waterproof Chukka Boot (Men)$89.97Current Price $89.97(47% off)47% off.$169.95Comparable value $169.95(9)
NUNN BUSHDenali Waterproof Plain Toe Boot - Wide Width Available$99.97Current Price $99.97(16% off)16% off.$120.00Comparable value $120.00(1)
Johnston & MurphyHenson XC4 Waterproof Chukka Boot (Men)$99.97Current Price $99.97(49% off)49% off.$199.00Comparable value $199.00(18)
New MarkdownAllen EdmondsGraham Chukka Boot (Men)$119.98Current Price $119.98(75% off)75% off.$495.00Comparable value $495.00(17)Only a few left
New!Marc Joseph New YorkChicago Chukka Boot (Men)$79.97Current Price $79.97(58% off)58% off.$195.00Comparable value $195.00(1)
La MilanoAcross II Cap Toe Chukka Boot (Men)$79.97Current Price $79.97(20% off)20% off.$99.99Comparable value $99.99
Donald PlinerSeya Chukka Boot (Men)$83.98 – $139.97Current Price $83.98 to $139.97(Up to 74% off select items)Up to 74% off select items.$325.00Comparable value $325.00
EastlandJack Chukka Boot (Men)$99.97Current Price $99.97(20% off)20% off.$125.00Comparable value $125.00(1)
araLangdon Chukka Boot (Men)$99.97Current Price $99.97(50% off)50% off.$200.00Comparable value $200.00(1)Only a few left
Clarks®Wallaston Low Chukka Boot (Men)$84.97Current Price $84.97(22% off)22% off.$110.00Comparable value $110.00
VANCE COJimmy Plain Toe Vegan Leather Chukka Boot (Men)$39.99Current Price $39.99(63% off)63% off.$109.99Comparable value $109.99Only a few left
Tod'sIdeal Suede Chukka Boot (Men)$249.97Current Price $249.97(57% off)57% off.$595.00Comparable value $595.00
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)
UGG®Neumel Chukka Boot (Men)$109.97Current Price $109.97(26% off)26% off.$150.00Comparable value $150.00(461)Only a few left
Maison ForteDaytona Chukka Boot (Men)$109.97Current Price $109.97(43% off)43% off.$195.00Comparable value $195.00(3)
Clarks®Walpath Waterproof Chukka Boot (Men)$99.97Current Price $99.97(23% off)23% off.$130.00Comparable value $130.00(1)Only a few left
New!MagnanniSuede Chukka Boot (Men)$239.97Current Price $239.97(51% off)51% off.$495.00Comparable value $495.00
New!Clarks® Originals'Desert' Boot (Men)$129.97Current Price $129.97(3% off)3% off.$135.00Comparable value $135.00(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(1)
New!MagnanniOslo Chukka Boot (Men)$239.97Current Price $239.97(49% off)49% off.$475.00Comparable value $475.00
JOHNSTON & MURPHY COLLECTIONWelch Chukka Boot (Men)$127.47Current Price $127.47(51% off)51% off.$265.00Comparable value $265.00(9)
JOHNSTON & MURPHY COLLECTIONMarlow Laceless Chukka Boot (Men)$59.96 – $79.97Current Price $59.96 to $79.97(Up to 77% off select items)Up to 77% off select items.$265.00Comparable value $265.00(2)
CARLOS SANTANACorazon Chukka Boot (Men)$89.96 – $119.97Current Price $89.96 to $119.97(Up to 43% off select items)Up to 43% off select items.$158.99Comparable value $158.99Only a few left
VinceJune Chukka Boot (Men)$97.48Current Price $97.48(74% off)74% off.$375.00Comparable value $375.00(1)
AllSaintsSkiff Chukka Boot (Men)$122.47Current Price $122.47(59% off)59% off.$299.00Comparable value $299.00(1)
FERRAGAMOGiasone Ankle Chukka Boot (Men)$379.97Current Price $379.97(60% off)60% off.$950.00Comparable value $950.00
VINTAGE FOUNDRYAnderson Casual Chukka Boot (Men)$119.97Current Price $119.97(31% off)31% off.$175.00Comparable value $175.00Only a few left
New!MagnanniLello Castagna Suede Boot (Men)$249.97Current Price $249.97(47% off)47% off.$475.00Comparable value $475.00
RESERVE FOOTWEARBaryon Leather Chukka Boot (Men)$79.97Current Price $79.97(32% off)32% off.$119.00Comparable value $119.00Only a few left
New MarkdownUGG®Neumel Shaggy Suede Chukka Boot (Men)$71.22Current Price $71.22(52% off)52% off.$150.00Comparable value $150.00(2)
SKECHERSx John Deere Segment 2.0 Waterproof Chelsea Boot (Men)$59.97Current Price $59.97(53% off)53% off.$128.00Comparable value $128.00(1)
New!MagnanniOslo Schore Chukka Boot (Men)$239.97Current Price $239.97(49% off)49% off.$475.00Comparable value $475.00
New MarkdownDr. MartensPatchwork Church Chukka Boot (Men)$89.96Current Price $89.96(55% off)55% off.$200.00Comparable value $200.00(3)Only a few left
SantoniGregory Chukka Boot (Men)$459.97Current Price $459.97(48% off)48% off.$890.00Comparable value $890.00(1)
TimberlandAttleboro Mid Chukka Boot (Men)$69.97Current Price $69.97(46% off)46% off.$130.00Comparable value $130.00(5)
ROANTimothy Suede Chukka Boot$69.97Current Price $69.97(29% off)29% off.$99.00Comparable value $99.00(2)
New MarkdownUGG®Neumal Crafted Regenerate Water Resistant Chukka Boot (Men)$74.96Current Price $74.96(62% off)62% off.$200.00Comparable value $200.00(4)Only a few left