Top DealAllen EdmondsCaden Lug Sole Chukka Boot$199.97Current Price $199.97(63% off)63% off.$550.00Comparable value $550.00(1)
Allen EdmondsHugo Lug Sole Boot$199.97Current Price $199.97(63% off)63% off.$550.00Comparable value $550.00(2)
Bruno MagliAnthony Lace-Up Boot$199.97Current Price $199.97(55% off)55% off.$450.00Comparable value $450.00
NewBruno MagliCat Walk Chukka Boot$159.97Current Price $159.97(54% off)54% off.$350.00Comparable value $350.00
NUNN BUSHCircuit Plain Toe Chukka Boot - Wide Width Available$54.97Current Price $54.97(Up to 45% off)Up to 45% off.$90.00 – $100.00Comparable value $90.00 to $100.00(17)
Josef SeibelStuart Chukka$45.48Current Price $45.48(74% off)74% off.$180.00Comparable value $180.00(1)
NewBruno MagliVincenzo Wingtip Boot$199.97Current Price $199.97(55% off)55% off.$450.00Comparable value $450.00
Allen EdmondsAlgonquin Lugged Chelsea Boot$199.97 – $299.97Current Price $199.97 to $299.97(Up to 66% off)Up to 66% off.$495.00 – $595.00Comparable value $495.00 to $595.00(4)
NewBruno MagliCarlo Leather Chukka Boot$179.97Current Price $179.97(52% off)52% off.$375.00Comparable value $375.00
NewDune LondonMatias Cap Toe Boot$119.97Current Price $119.97(51% off)51% off.$249.00Comparable value $249.00
Dune LondonClaus Chukka Boot$89.97Current Price $89.97(50% off)50% off.$180.00Comparable value $180.00(1)
NewMilwaukee Boot CompanyWhitnall Chukka Boot$169.97Current Price $169.97(30% off)30% off.$245.00Comparable value $245.00
TecovasThe Rugged Moc Toe Boot$129.97Current Price $129.97(42% off)42% off.$225.00Comparable value $225.00(1)
BarbourSheene Moc Toe Boot$149.97Current Price $149.97(48% off)48% off.$290.00Comparable value $290.00(2)
NewBOSSKope Suede Chukka Boot$129.97Current Price $129.97(43% off)43% off.$230.00Comparable value $230.00
TAFTThe Darcey Moc Toe Boot$179.97Current Price $179.97(38% off)38% off.$295.00Comparable value $295.00(12)
FlorsheimFLORSHEIM Chalet Leather Cap Toe Boot$109.97Current Price $109.97(29% off)29% off.$155.00Comparable value $155.00(27)
NewStuart WeitzmanAdam Lace-Up Boot$239.97Current Price $239.97(64% off)64% off.$675.00Comparable value $675.00
TO BOOT NEW YORKHorace Chukka Boot$199.97Current Price $199.97(52% off)52% off.$425.00Comparable value $425.00 Only a few left
Allen EdmondsLandon Boot$249.97Current Price $249.97(54% off)54% off.$550.00Comparable value $550.00(3)
NewFRYE AND CODunn Leather Lace Up Boot$99.97Current Price $99.97(53% off)53% off.$214.99Comparable value $214.99
Dune LondonClydell Chukka Boot$94.97Current Price $94.97(51% off)51% off.$195.00Comparable value $195.00
BarbourMaxwell Waterproof Chukka Boot$119.97Current Price $119.97(50% off)50% off.$240.00Comparable value $240.00(1)
BarbourBlaine Chukka Boot$129.97Current Price $129.97(46% off)46% off.$245.00Comparable value $245.00
Allen EdmondsCarson Hybrid Chukka Boot$189.97Current Price $189.97(51% off)51% off.$395.00Comparable value $395.00(27) Only a few left
MADDENTaskorn Combat Boot$54.97Current Price $54.97(38% off)38% off.$90.00Comparable value $90.00(53)
ROANCass Distressed Leather Boot$109.09Current Price $109.09(21% off)21% off.$139.00Comparable value $139.00 Only a few left
BarbourTiller Moc Toe Boot$129.97Current Price $129.97(43% off)43% off.$230.00Comparable value $230.00(1)
TAFTThe Boston Longwing Boot$159.97Current Price $159.97(45% off)45% off.$295.00Comparable value $295.00(35)
Bruno MagliScotty Lugged Moc Toe Combat Boot$199.97Current Price $199.97(55% off)55% off.$450.00Comparable value $450.00(1)
AllSaintsSkiff Mid Boot$190.97Current Price $190.97(40% off)40% off.$319.00Comparable value $319.00 Only a few left
Bruno MagliPhilip Lace-Up Boot$269.97Current Price $269.97(40% off)40% off.$450.00Comparable value $450.00(1)
NewCamperPix Leather Boot$139.97Current Price $139.97(34% off)34% off.$215.00Comparable value $215.00 Only a few left
BarbourHadston Chukka Boot$129.97Current Price $129.97(45% off)45% off.$240.00Comparable value $240.00
NewCole Haan2.ZEROGRAND Chukka Boot$109.97Current Price $109.97(68% off)68% off.$345.00Comparable value $345.00
Dune LondonMarrow Lug Sole Boot$99.97Current Price $99.97(52% off)52% off.$210.00Comparable value $210.00
BarbourBoulder Chukka Boot$119.97Current Price $119.97(47% off)47% off.$230.00Comparable value $230.00(1)
Sperryx One Of These Days Tony Moc Toe Boot$119.97Current Price $119.97(60% off)60% off.$300.00Comparable value $300.00
VANCE COFegan Cap Toe Boot$59.97 – $69.97Current Price $59.97 to $69.97(Up to 45% off)Up to 45% off.$109.99Comparable value $109.99(1)
FERRAGAMOIuri Combat Boot$499.97Current Price $499.97(57% off)57% off.$1,190.00Comparable value $1,190.00
NewGentle SoulsTorres Chukka Boot$95.97Current Price $95.97(61% off)61% off.$250.00Comparable value $250.00
G.H.BASSWallace Two-Eye Lace-up Shoe$84.97Current Price $84.97(62% off)62% off.$225.00Comparable value $225.00(1) Only a few left
Dr. MartensGender Inclusive 1460 Pascal Desert Brown Boot$89.97Current Price $89.97(47% off)47% off.$170.00Comparable value $170.00(8) Only a few left
NewCamperBeetle Sneaker$134.97Current Price $134.97(34% off)34% off.$205.00Comparable value $205.00(1)
NewVINTAGE FOUNDRYHayden Boot$29.97Current Price $29.97(88% off)88% off.$269.00Comparable value $269.00(4) Only a few left
NewDr. Scholl'sSyncflex Chukka Boot$74.97Current Price $74.97(31% off)31% off.$110.00Comparable value $110.00
AlignEddy Waterproof Leather Boot$99.97Current Price $99.97(44% off)44% off.$179.95Comparable value $179.95
G.H.BASS1876 Quail Hunter Boot$119.97Current Price $119.97(63% off)63% off.$325.00Comparable value $325.00(3) Only a few left
Anthony VeerLincoln Lug Sole Boot$149.97Current Price $149.97(38% off)38% off.$244.95Comparable value $244.95
MADDENTaskorn Combat Boot$54.97Current Price $54.97(38% off)38% off.$90.00Comparable value $90.00(13)
Johnston & MurphyUpton Chukka$129.97Current Price $129.97(27% off)27% off.$179.00Comparable value $179.00
Allen EdmondsPark Avenue Verse Cap Toe Oxford Boot$209.97Current Price $209.97(61% off)61% off.$550.00Comparable value $550.00(8) Only a few left
Dr. Martens101 Lace-Up Boot$119.97Current Price $119.97(29% off)29% off.$170.00Comparable value $170.00(6)
EastlandJack Chukka Boot$89.97Current Price $89.97(28% off)28% off.$125.00Comparable value $125.00(1)
Kenneth Cole ReactionVesto Chukka Boot$69.97Current Price $69.97(41% off)41% off.$119.00Comparable value $119.00(1)
Warfield & GrandOrbit Cap Toe Derby$59.97Current Price $59.97(63% off)63% off.$165.00Comparable value $165.00(12)
MerrellWilderness Sneaker$159.97Current Price $159.97(42% off)42% off.$280.00Comparable value $280.00(2)
NewJohnston & MurphyCalder Chukka Boot$68.97 – $116.97Current Price $68.97 to $116.97(Up to 58% off)Up to 58% off.$165.00 – $189.00Comparable value $165.00 to $189.00(29)
NUNN BUSHChase Plain Toe Chukka Boot - Wide Width Available$44.97 – $49.97Current Price $44.97 to $49.97(Up to 52% off)Up to 52% off.$90.00 – $95.00Comparable value $90.00 to $95.00(14)
NewMilwaukee Boot CompanyHighland Waterproof Boot$209.97Current Price $209.97(28% off)28% off.$295.00Comparable value $295.00
Donald PlinerSeya Chukka Boot$139.97Current Price $139.97(56% off)56% off.$325.00Comparable value $325.00(1) Only a few left
NewDr. Scholl'sAugust Faux Leather Boot$64.97Current Price $64.97(35% off)35% off.$100.00Comparable value $100.00
JordanCity Boot$59.97Current Price $59.97(66% off)66% off.$180.00Comparable value $180.00(3) Only a few left
ROANLecture Leather Lace-Up Boot$109.97Current Price $109.97(21% off)21% off.$140.00Comparable value $140.00 Only a few left
Tod'sIdeal Suede Chukka Boot$249.97Current Price $249.97(57% off)57% off.$595.00Comparable value $595.00(1)
FERRAGAMOGreenwich Lace-Up Boot$799.97Current Price $799.97(49% off)49% off.$1,590.00Comparable value $1,590.00 Only a few left