tamarindblackblackgreydark sapphireUGG®UGG Maksim Chukka Boot (Men)$27.98 – $79.97$79.97 – $125.00up to 65% off select colors/sizes(320)Free Shipping on Orders $89+
ch umbriablackCole HaanGrandOS 360 York Chelsea Boot (Men)$97.49 – $119.97$250.00up to 61% off select colors/sizes(4)Free Shipping on Orders $89+
ch lumber wr/ivorywren brown wr/ch oatCole HaanGrand Atlantic Chukka Boot (Men)$99.97$200.0050% off(1)Free Shipping on Orders $89+
brown/browndark brownCole HaanZero Grand Hiker Waterproof Boot$99.97$320.0068% off(4)Free Shipping on Orders $89+
brown leatherblack leatherNordstromMason Water Resistant Chelsea Boot (Men)$53.97$119.9555% off(5)Free Shipping on Orders $89+
NUNN BUSHBarklay Leather Plain Toe Chukka Boot - Wide Width Available$49.97$95.0047% off(10)Free Shipping on Orders $89+
blackdark greydark brownDr. Scholl'sDR. SCHOLLS Lancer Leather Chukka Boot (Men)$49.97 – $54.99$85.00up to 41% off select colors/sizes(3)Free Shipping on Orders $89+
grey oiled suedeblackolive oiled suedeNordstromWilliam Waterproof Side Zip Boot (Men)$64.97 – $97.46$129.95up to 50% off select colors/sizes(4)Free Shipping on Orders $89+
SperryTop Sider Gold Cup Authentic Original Chukka Boot$59.96$185.0067% off(1)Free Shipping on Orders $89+
TimberlandPort Union Waterproof Chukka Boot (Men)$89.97$165.0045% off(74)Free Shipping on Orders $89+
FlorsheimForest Plain Toe Leather Chukka Boot (Men)$59.97$115.0047% off(1)Free Shipping on Orders $89+
multi - assortedlight beigeCamperGround Sneaker Boot (Men)$189.97$299.0036% off(1)Free Shipping on Orders $89+
black chbrown cholive suedeFlorsheimField Gore Boot (Men)$44.96 – $59.97$110.00up to 59% off select colors/sizes(1)Free Shipping on Orders $89+
black leatherbrown leatherNordstromMaddox Chukka Boot (Men)$54.97$109.9550% off(3)Free Shipping on Orders $89+
FlorsheimChalet Leather Moc Toe Side Zip Boot (Men)$79.97$135.0040% off(2)Free Shipping on Orders $89+
NordstromMax Water Resistant Lug Chelsea Boot (Men)$49.97$99.9550% off(6)Only a few leftFree Shipping on Orders $89+
RockportWeather or Not Waterproof Moc Toe Leather Boot$89.97$150.0040% off(8)Free Shipping on Orders $89+
SperryAuthentic Original Waterproof Moc Toe Boot (Men)$69.97$180.0061% off(20)Free Shipping on Orders $89+
NUNN BUSHFinn Cap Toe Chukka Boot (Men)$39.97$100.0060% offOnly a few leftFree Shipping on Orders $89+
CREVOBennington Faux Shearling Lined Leather Lace-Up Boot (Men)$59.96$100.0040% offFree Shipping on Orders $89+
RockportWaterproof Leather Moc Toe Lug Sole Boot (Men)$79.97$150.0046% off(4)Free Shipping on Orders $89+
dark brownblackDr. Scholl'sCavalry Combat Boot (Men)$69.97 – $79.97$150.00up to 53% off select colors/sizes(4)Free Shipping on Orders $89+
Cole HaanLace-Front Grand 360 Nubuck Leather Mid Boot (Men)$119.97$260.0053% offOnly a few leftFree Shipping on Orders $89+
brownchestnutCREVOAiden Leather Lace-Up Boot (Men)$52.46 – $69.97$95.00up to 44% off select colors/sizesFree Shipping on Orders $89+
charcoalbrown chtan multiNUNN BUSHCompass Waterproof Plain Toe Boot$59.97$100.0040% off(2)Free Shipping on Orders $89+
Sandro MoscoloniEyelet Plain Toe Leather Demi Boot (Men)$180.00Only a few leftFree Shipping on Orders $89+