BørnThomson Chukka Boot (Men)$89.97Current Price $89.97(30% off)30% off.$130.00Comparable value $130.00(25)
New!BørnTheo Chukka Boot (Men)$79.97Current Price $79.97(38% off)38% off.$130.00Comparable value $130.00(5)
Clarks®Craftwell Lace-Up Boot (Men)$79.97Current Price $79.97(27% off)27% off.$110.00Comparable value $110.00
Black Friday DealUGG®Burleigh Chukka (Men)$89.97Current Price $89.97(43% off)43% off.$160.00Comparable value $160.00(10)
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)
Johnston & MurphyBoswell Chukka Boot (Men)$89.97Current Price $89.97(48% off)48% off.$175.00Comparable value $175.00(4)
New!AriatSpitfire All Terrain Waterproof Chukka Boot (Men)$89.97Current Price $89.97(47% off)47% off.$169.95Comparable value $169.95(2)
The North FaceNSE Chukka Boot (Men)$59.97Current Price $59.97(44% off)44% off.$109.00Comparable value $109.00
New!Clarks®Maplewalk Rise Boot (Men)$89.97Current Price $89.97(25% off)25% off.$120.00Comparable value $120.00
New!ReefSwellsole Scallywag Waterproof Boot (Men)$49.97Current Price $49.97(52% off)52% off.$105.00Comparable value $105.00
New!Clarks®Walpath Waterproof Chukka Boot (Men)$99.97Current Price $99.97(23% off)23% off.$130.00Comparable value $130.00
New!AlesburyRodale Boot (Men)$39.97Current Price $39.97(52% off)52% off.$85.00Comparable value $85.00
New!Marc Joseph New YorkHudson Yards 2.0 Pull-On Boot (Men)$79.97Current Price $79.97(58% off)58% off.$195.00Comparable value $195.00
NUNN BUSHKarnak Water Resistant Plain Toe Boot (Men)$89.97Current Price $89.97(18% off)18% off.$110.00Comparable value $110.00
PalladiumPampa Hi Canvas Boot (Men)$29.97Current Price $29.97(Up to 57% off select items)Up to 57% off select items.$29.97 – $70.00Comparable value $29.97 to $70.00(11)
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)
NUNN BUSHKarnak Water Resistant Moc Toe Boot (Men)$89.97Current Price $89.97(18% off)18% off.$110.00Comparable value $110.00(3)
New!SORELMadson II Waterproof Chukka Boot (Men)$99.97Current Price $99.97(47% off)47% off.$190.00Comparable value $190.00(15)Only a few left
Clarks®Maplewalk Moc Toe Boot (Men)$79.97Current Price $79.97(33% off)33% off.$120.00Comparable value $120.00(6)
New!TimberlandAttleboro Chelsea Boot (Men)$69.97 – $74.97Current Price $69.97 to $74.97(46% off)46% off.$130.00 – $140.00Comparable value $130.00 to $140.00(3)
Clarks®Maplewalk Waterproof Boot (Men)$89.97Current Price $89.97(25% off)25% off.$120.00Comparable value $120.00(4)
Black Friday DealRESERVE FOOTWEARGerard Lug Sole Boot (Men)$44.99Current Price $44.99(64% off)64% off.$125.00Comparable value $125.00(3)
Black Friday DealVINTAGE FOUNDRYTreyton Chukka Boot (Men)$74.99Current Price $74.99(62% off)62% off.$200.00Comparable value $200.00(4)
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)
NUNN BUSHTrekker Mid Sneaker (Men)$54.97Current Price $54.97(35% off)35% off.$85.00Comparable value $85.00(2)
Tommy HilfigerHarbin Chukka Boot (Men)$59.97Current Price $59.97(49% off)49% off.$119.00Comparable value $119.00(6)
New!Dune LondonCarden Chelsea Boot (Men)$89.97Current Price $89.97(50% off)50% off.$180.00Comparable value $180.00
Deer StagsGarfield Plain Toe Chukka Boot (Men)$64.97Current Price $64.97(35% off)35% off.$100.00Comparable value $100.00
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(10)
NUNN BUSHExcavate Water Resistant Moc Toe Boot (Men)$69.97Current Price $69.97(26% off)26% off.$95.00Comparable value $95.00(4)
NUNN BUSHOzark II Chukka Boot (Men)$94.97Current Price $94.97(13% off)13% off.$110.00Comparable value $110.00(3)
NUNN BUSHKarnak Plain Toe Chelsea Boot (Men)$89.97Current Price $89.97(25% off)25% off.$120.00Comparable value $120.00
Cole Haan2.Zerogrand Chukka Boot (Men)$99.97Current Price $99.97(70% off)70% off.$338.00Comparable value $338.00(388)
FlorsheimChalet Chelsea Boot (Men)$99.97Current Price $99.97(31% off)31% off.$145.00Comparable value $145.00(108)
NUNN BUSHDelton Plain Toe Chukka Boot (Men)$54.97Current Price $54.97(42% off)42% off.$95.00Comparable value $95.00
VINTAGE FOUNDRYBlaise Ankle Boot (Men)$99.97Current Price $99.97(62% off)62% off.$269.00Comparable value $269.00
Black Friday DealKARL LAGERFELD PARISFaux Shearling Lined Double Buckle Boot (Men)$49.99Current Price $49.99(77% off)77% off.$225.00Comparable value $225.00(12)
JOHNSTON & MURPHY COLLECTIONMarlow Laceless Chukka Boot (Men)$79.97Current Price $79.97(69% off)69% off.$265.00Comparable value $265.00(2)
ROANTimothy Suede Chukka Boot$69.97Current Price $69.97(29% off)29% off.$99.00Comparable value $99.00(2)
Dr. MartensZuma II Boot (Men)$74.97Current Price $74.97(42% off)42% off.$130.00Comparable value $130.00(7)
New!Clarks®Walpath Waterproof Chelsea Boot (Men)$99.97Current Price $99.97(23% off)23% off.$130.00Comparable value $130.00
Clarks®Shepton Chukka Boot (Men)$74.97Current Price $74.97(31% off)31% off.$110.00Comparable value $110.00
Black Friday DealUGG®Emmett Waterproof Snow Boot (Men)$64.99Current Price $64.99(56% off)56% off.$150.00Comparable value $150.00(83)
SORELScout 87 Pro Plus Waterproof Boot (Men)$99.97Current Price $99.97(44% off)44% off.$180.00Comparable value $180.00
Black Friday DealPalladiumPallabrousse Legion Boot (Men)$27.99Current Price $27.99(65% off)65% off.$80.00Comparable value $80.00(5)
TimberlandField Trekker Waterproof Boot (Men)$69.97Current Price $69.97(36% off)36% off.$110.00Comparable value $110.00(3)
adidasTerrex Anylander Mid R.RDY Waterproof Hiking Boot (Men)$79.97Current Price $79.97(20% off)20% off.$100.00Comparable value $100.00(446)
OluKaiNalukai Kala Moc Toe Boot (Men)$69.97Current Price $69.97(50% off)50% off.$140.00Comparable value $140.00(1)
New!SKECHERSx John Deere Relaxed Fit Terraform Waterproof Boot (Men)$59.97Current Price $59.97(55% off)55% off.$135.00Comparable value $135.00(9)
Clarks®Radcliff Plain Toe Chukka Boot (Men)$89.97Current Price $89.97(25% off)25% off.$120.00Comparable value $120.00(1)
RESERVE FOOTWEARZion Chukka Boot (Men)$39.97Current Price $39.97(50% off)50% off.$80.00Comparable value $80.00(2)
Black Friday DealVINTAGE FOUNDRYCharles Chelsea Boot (Men)$69.99Current Price $69.99(62% off)62% off.$185.00Comparable value $185.00(4)
SORELAnkeny II Plus Waterproof Hiking Boot (Men)$99.97Current Price $99.97(42% off)42% off.$175.00Comparable value $175.00(1)
ALDOKenora Chukka Boot (Men)$59.97Current Price $59.97(53% off)53% off.$130.00Comparable value $130.00
Black Friday DealDockers®Esmond Chukka Boot (Men)$54.99Current Price $54.99(42% off)42% off.$95.00Comparable value $95.00
Ben ShermanThames Chukka Boot (Men)$74.97Current Price $74.97(34% off)34% off.$115.00Comparable value $115.00
Black Friday DealUGG®The UGG Lug Waterproof Chukka Boot (Men)$79.97Current Price $79.97(38% off)38% off.$130.00Comparable value $130.00
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)
EastlandFinn Plain Toe Boot (Men)$59.97Current Price $59.97(33% off)33% off.$90.00Comparable value $90.00(2)
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
New!Clarks®Wallaston Chukka Boot (Men)$79.97Current Price $79.97(33% off)33% off.$120.00Comparable value $120.00
TimberlandNewmarket Chukka Boot (Men)$89.97Current Price $89.97(40% off)40% off.$150.00Comparable value $150.00(5)
New!Clarks®Weltridge Side Zip Boot (Men)$94.97Current Price $94.97(26% off)26% off.$130.00Comparable value $130.00
New!Cole HaanGrand Atlantic Chelsea Boot (Men)$99.97Current Price $99.97(50% off)50% off.$200.00Comparable value $200.00(2)
Hey DudeWally Mid Chukka Boot (Men)$39.97Current Price $39.97(42% off)42% off.$69.99Comparable value $69.99(12)
VINTAGE FOUNDRYMarlow Chukka Boot (Men)$89.97Current Price $89.97(51% off)51% off.$185.00Comparable value $185.00
VANCE COSlater Chelsea Boot (Men)$74.97Current Price $74.97(31% off)31% off.$109.99Comparable value $109.99
Dr. Scholl'sCharge Work Boot - Wide Width Available$84.97Current Price $84.97(34% off)34% off.$130.00Comparable value $130.00(44)
Dockers®Dee Chukka Boot (Men)$39.97Current Price $39.97(57% off)57% off.$95.00Comparable value $95.00
Cole HaanGrand Atlantic Chukka Boot - Wide Width Available (Men)$99.97Current Price $99.97(50% off)50% off.$200.00Comparable value $200.00(38)
New!TimberlandAttleboro Mid Chukka Boot (Men)$69.97Current Price $69.97(46% off)46% off.$130.00Comparable value $130.00(4)