Steve MaddenSawyer Chelsea Boot (Men)$49.97Current Price $49.97(44% off)44% off.$90.00Comparable value $90.00(9)
Dr. Martens2976 Wintergrip Water Resistant Chelsea Boot (Men)$99.97Current Price $99.97(47% off)47% off.$190.00Comparable value $190.00(47)
FlorsheimChalet Chelsea Boot (Men)$99.97Current Price $99.97(31% off)31% off.$145.00Comparable value $145.00(111)
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)
UGG®Classic Mini Boot (Men)$89.97Current Price $89.97(43% off)43% off.$160.00Comparable value $160.00(10)Only a few left
Steve MaddenScotch Lug Sole Boot (Men)$79.97Current Price $79.97(38% off)38% off.$130.00Comparable value $130.00(1)
New!Johnston & MurphyBorland Chelsea Boot (Men)$79.97Current Price $79.97(50% off)50% off.$160.00Comparable value $160.00(1)
New!Ted BakerNorwich Chelsea Boot (Men)$89.97Current Price $89.97(52% off)52% off.$190.00Comparable value $190.00
Tommy HilfigerSesame Chelsea Boot (Men)$54.97Current Price $54.97(53% off)53% off.$119.00Comparable value $119.00(30)
ALDOKenora Chukka Boot (Men)$59.97Current Price $59.97(53% off)53% off.$130.00Comparable value $130.00(1)
Dr. Martens1460 Pascal Waterproof Fleece Lined Boot (Men)$99.97Current Price $99.97(44% off)44% off.$180.00Comparable value $180.00(23)Only a few left
Steve MaddenHemet Chukka Boot (Men)$74.97Current Price $74.97(42% off)42% off.$130.00Comparable value $130.00(3)
Steve MaddenRilyn Chelsea Boot (Men)$79.97Current Price $79.97(50% off)50% off.$160.00Comparable value $160.00(12)
Johnston & MurphyBoswell Chukka Boot (Men)$89.97Current Price $89.97(48% off)48% off.$175.00Comparable value $175.00(10)
ALDOToney Waterproof Wingtip Boot (Men)$79.97Current Price $79.97(23% off)23% off.$105.00Comparable value $105.00Only a few left
Tommy HilfigerHarbin Chukka Boot (Men)$59.97Current Price $59.97(49% off)49% off.$119.00Comparable value $119.00(7)
MADDENTaskorn Combat Boot (Men)$54.97Current Price $54.97(38% off)38% off.$90.00Comparable value $90.00(40)
New!Steve MaddenMemille Chelsea Boot (Men)$54.97Current Price $54.97(35% off)35% off.$85.00Comparable value $85.00
Clarks®Weltridge Side Zip Boot (Men)$94.97Current Price $94.97(26% off)26% off.$130.00Comparable value $130.00(2)
ALDOJefry Chukka Boot (Men)$69.97Current Price $69.97(50% off)50% off.$140.00Comparable value $140.00
New!La MilanoJaxon II Cap Toe Boot (Men)$79.97Current Price $79.97(20% off)20% off.$99.99Comparable value $99.99
ALDOBristoll Ankle Boot (Men)$16.78 – $52.47Current Price $16.78 to $52.47(Up to 88% off select items)Up to 88% off select items.$140.00Comparable value $140.00(3)
Dockers®Truman Chelsea Boot (Men)$59.97Current Price $59.97(36% off)36% off.$95.00Comparable value $95.00(1)
BørnTheo Chukka Boot (Men)$59.97 – $79.97Current Price $59.97 to $79.97(Up to 53% off select items)Up to 53% off select items.$130.00Comparable value $130.00(6)
EastlandJack Chukka Boot (Men)$89.97Current Price $89.97(28% off)28% off.$125.00Comparable value $125.00(1)
BørnSeth Chukka Boot (Men)$89.97Current Price $89.97(35% off)35% off.$140.00Comparable value $140.00(7)
New!TimberlandAttleboro Chelsea Boot (Men)$69.97Current Price $69.97(Up to 50% off)Up to 50% off.$130.00 – $140.00Comparable value $130.00 to $140.00(7)
MADDENEstiban Chelsea Boot (Men)$54.97Current Price $54.97(35% off)35% off.$85.00Comparable value $85.00(4)
Tommy HilfigerRoklan Chelsea Boot (Men)$59.97Current Price $59.97(53% off)53% off.$129.00Comparable value $129.00
Clarks®Wallaston Chukka Boot (Men)$79.97Current Price $79.97(33% off)33% off.$120.00Comparable value $120.00(1)
UGG®Emmett Waterproof Snow Boot (Men)$79.97Current Price $79.97(46% off)46% off.$150.00Comparable value $150.00(122)
VINTAGE FOUNDRYTreyton Chukka Boot (Men)$99.97Current Price $99.97(50% off)50% off.$200.00Comparable value $200.00(5)
Steve MaddenPeter Boot (Men)$89.97Current Price $89.97(47% off)47% off.$170.00Comparable value $170.00(1)
MADDENBronnie Combat Boot (Men)$59.97Current Price $59.97(40% off)40% off.$100.00Comparable value $100.00(1)
AriatSport Stratten Leather Boot (Men)$99.97Current Price $99.97(47% off)47% off.$189.95Comparable value $189.95(51)Only a few left
Dr. MartensCombs Lug Sole Combat Boot (Men)$89.97Current Price $89.97(18% off)18% off.$110.00Comparable value $110.00(53)
Clarks®Shepton Easy Chelsea Boot (Men)$94.97Current Price $94.97(26% off)26% off.$130.00Comparable value $130.00
Dr. Martens2976 Leather Chelsea Boot (Men)$99.97Current Price $99.97(44% off)44% off.$180.00Comparable value $180.00(1)Only a few left
Johnston & MurphyUpton Chukka Boot (Men)$69.97Current Price $69.97(58% off)58% off.$169.00Comparable value $169.00(18)
VINTAGE FOUNDRYLyle Chelsea Boot (Men)$74.97 – $99.97Current Price $74.97 to $99.97(Up to 62% off select items)Up to 62% off select items.$200.00Comparable value $200.00(2)
Rush by Gordon RushChelsea Boot (Men)$49.97Current Price $49.97(60% off)60% off.$125.00Comparable value $125.00(36)
Clear The RackCole HaanGrand Chelsea Boot (Men)$41.23Current Price $41.23(Extra 25% off)Includes extra 25% off.$54.98Previous Price $54.98$150.00Comparable value $150.00
New!Tommy HilfigerGainsly Chelsea Boot (Men)$59.97Current Price $59.97(52% off)52% off.$125.00Comparable value $125.00
New!Clarks®Wallaston Low Chukka Boot (Men)$84.97Current Price $84.97(22% off)22% off.$110.00Comparable value $110.00
TimberlandNewmarket Chukka Boot (Men)$89.97Current Price $89.97(40% off)40% off.$150.00Comparable value $150.00(6)
New!EastlandJack Chukka Boot (Men)$99.97Current Price $99.97(20% off)20% off.$125.00Comparable value $125.00(1)
Tommy HilfigerBerton Chelsea Boot (Men)$59.97Current Price $59.97(49% off)49% off.$119.00Comparable value $119.00
Rush by Gordon RushApron Toe Boot (Men)$54.97Current Price $54.97(56% off)56% off.$125.00Comparable value $125.00(10)
New!MADDENBrycee Lug Sole Boot (Men)$64.97Current Price $64.97(35% off)35% off.$100.00Comparable value $100.00(1)
Steve MaddenAddis Brogue Boot (Men)$84.97Current Price $84.97(41% off)41% off.$145.00Comparable value $145.00
Clear The RackAllSaintsHollow Zip Leather Boot (Men)$84.35Current Price $84.35(Extra 25% off)Includes extra 25% off.$112.47Previous Price $112.47$299.00Comparable value $299.00(7)
TimberlandAttleboro Mid Chukka Boot (Men)$69.97Current Price $69.97(46% off)46% off.$130.00Comparable value $130.00(5)
Dr. MartensZuma II Boot (Men)$74.97Current Price $74.97(42% off)42% off.$130.00Comparable value $130.00(10)
SORELHi-Line Waterproof Lace-Up Boot (Men)$89.97Current Price $89.97(51% off)51% off.$185.00Comparable value $185.00(27)
Johnston & MurphyCalder Chukka Boot (Men)$79.97Current Price $79.97(51% off)51% off.$165.00Comparable value $165.00(21)
MADDENLennie Lug Sole Boot (Men)$64.97Current Price $64.97(35% off)35% off.$100.00Comparable value $100.00(6)
WINTHROPOakridge Lug Sole Boot (Men)$59.97Current Price $59.97(65% off)65% off.$175.00Comparable value $175.00(3)
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
SORELSlabtown '62™ Waterproof Moc Toe Boot (Men)$99.97Current Price $99.97(42% off)42% off.$175.00Comparable value $175.00(4)Only a few left
Eastland'Lumber Up' Moc Toe Boot (Men)$74.97 – $99.97Current Price $74.97 to $99.97(Up to 50% off select items)Up to 50% off select items.$135.00 – $150.00Comparable value $135.00 to $150.00(4)
Clear The RackRESERVE FOOTWEARDevon Lace-Up Boot (Men)$33.74Current Price $33.74(Extra 25% off)Includes extra 25% off.$44.99Previous Price $44.99$125.00Comparable value $125.00(1)Only a few left
Tommy HilfigerBlaze Lace Cap Toe Boot (Men)$59.97Current Price $59.97(49% off)49% off.$119.00Comparable value $119.00
EastlandSeth Memory Foam Chukka Boot (Men)$44.97Current Price $44.97(50% off)50% off.$90.00Comparable value $90.00(1)
Kurt Geiger LondonHunt Chelsea Boot (Men)$89.97Current Price $89.97(68% off)68% off.$285.00Comparable value $285.00Only a few left
MADDENTaskorn Combat Boot (Men)$54.97Current Price $54.97(38% off)38% off.$90.00Comparable value $90.00(7)
Cole Haan2.Zerogrand Chukka Boot (Men)$99.97Current Price $99.97(70% off)70% off.$338.00Comparable value $338.00(397)
Dockers®Esmond Plain Toe Chukka Boot (Men)$69.97Current Price $69.97(17% off)17% off.$85.00Comparable value $85.00(5)
Cole HaanChamberlin Grand Chukka Boot (Men)$97.47 – $129.97Current Price $97.47 to $129.97(Up to 66% off select items)Up to 66% off select items.$290.00Comparable value $290.00(1)
SORELMadson II Chore Waterproof Boot (Men)$99.97Current Price $99.97(48% off)48% off.$195.00Comparable value $195.00(12)
KARL LAGERFELD PARISSuede Chelsea Boot (Men)$89.97Current Price $89.97(64% off)64% off.$250.00Comparable value $250.00(7)