“chukka and Men Boots” we found 226 items!

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View More Like This Eastland 1955 Edition - Seneca Eastland 1955 Edition Seneca $110.00 $98.99 Rated: 5 stars! View More Like This Eastland 1955 Edition - Seneca Eastland 1955 Edition Seneca $110.00 Rated: 5 stars! View More Like This ECCO - Turn GTX Boot ECCO Turn GTX Boot $230.00 Rated: 5 stars! View More Like This Dr. Martens - Sawyer Desert Boot Dr. Martens Sawyer Desert Boot $130.00 Rated: 5 stars!
View More Like This SKECHERS - Relaxed Fit Segment - Barillo SKECHERS Relaxed Fit Segment - Barillo $85.00 Rated: 5 stars! View More Like This Timberland - Groveton Plain Toe Chukka Leather and Fabric Timberland Groveton Plain Toe Chukka Leather and Fabric $90.00 Rated: 5 stars! View More Like This Timberland - Earthkeepers® Brook Park Chukka Timberland Earthkeepers® Brook Park Chukka $110.00 Rated: 5 stars! View More Like This Timberland - Groveton Plain Toe Chukka Leather and Fabric Timberland Groveton Plain Toe Chukka Leather and Fabric $90.00 Rated: 5 stars!
View More Like This OluKai - Pahoa OluKai Pahoa $200.00 Rated: 5 stars! View More Like This OluKai - Pahoa OluKai Pahoa $200.00 Rated: 5 stars! View More Like This OluKai - Pahoa OluKai Pahoa $200.00 Rated: 5 stars! View More Like This Wolverine - Cort Waterproof Leather Chukka Wolverine Cort Waterproof Leather Chukka $160.00 Rated: 5 stars!
View More Like This Wolverine - Cort Waterproof Leather Chukka Wolverine Cort Waterproof Leather Chukka $160.00 Rated: 5 stars! View More Like This Merrell - Epiction Merrell Epiction $159.95 Rated: 5 stars! View More Like This Merrell - Epiction Merrell Epiction $159.95 $144.99 Rated: 5 stars! View More Like This Merrell - Epiction Merrell Epiction $159.95 $127.99 Rated: 5 stars!
View More Like This Timberland - West Haven Chukka Timberland West Haven Chukka $160.00 $127.99 Rated: 5 stars! View More Like This Timberland - Britton Hill Waterproof Chukka Timberland Britton Hill Waterproof Chukka $180.00 $162.99 Rated: 5 stars! View More Like This Clarks - Newkirk Top Clarks Newkirk Top $135.00 Rated: 5 stars! View More Like This Woolrich - Beebe Leather Woolrich Beebe Leather $180.00 Rated: 5 stars!
View More Like This Frye - James Lug Chukka Shearling Frye James Lug Chukka Shearling $388.00 $310.40 Rated: 5 stars! View More Like This Clarks - Newkirk Top Clarks Newkirk Top $135.00 Rated: 5 stars! View More Like This Frye - James Lug Chukka Shearling Frye James Lug Chukka Shearling $388.00 $310.40 Rated: 5 stars! View More Like This Pikolinos - Ellesmere M6C-8069 Pikolinos Ellesmere M6C-8069 $215.00 $150.99 Rated: 5 stars!
View More Like This Josef Seibel - Oscar 11 Josef Seibel Oscar 11 $185.00 Rated: 5 stars! View More Like This Josef Seibel - Oscar 11 Josef Seibel Oscar 11 $185.00 Rated: 5 stars! View More Like This Volcom - Del Mesa 2 Volcom Del Mesa 2 $120.00 $107.99 Rated: 5 stars! View More Like This Volcom - Del Mesa 2 Volcom Del Mesa 2 $85.00 $75.99 Rated: 5 stars!
View More Like This Volcom - Del Mesa 2 Volcom Del Mesa 2 $85.00 $75.99 Rated: 5 stars! View More Like This TOMS - Mateo Chukka Boot TOMS Mateo Chukka Boot $119.00 $82.99 Rated: 5 stars! View More Like This Volcom - Del Mesa 2 Volcom Del Mesa 2 $85.00 $75.99 Rated: 5 stars! View More Like This Oliberte - Adibo Oliberte Adibo $120.00 Rated: 5 stars!
View More Like This Oliberte - Adibo Oliberte Adibo $120.00 Rated: 5 stars! View More Like This Rockport - Total Motion Fusion Desert Boot Rockport Total Motion Fusion Desert Boot $149.95 Rated: 5 stars! View More Like This Rockport - Total Motion Fusion Desert Boot Rockport Total Motion Fusion Desert Boot $149.95 $129.95 Rated: 5 stars! View More Like This TOMS - Mateo Chukka Boot TOMS Mateo Chukka Boot $98.00 Rated: 5 stars!
View More Like This TOMS - Mateo Chukka Boot TOMS Mateo Chukka Boot $119.00 $82.99 Rated: 5 stars! View More Like This TOMS - Mateo Chukka Boot TOMS Mateo Chukka Boot $98.00 Rated: 5 stars! View More Like This TOMS - Mateo Chukka Boot TOMS Mateo Chukka Boot $129.00 $90.99 Rated: 5 stars! View More Like This TOMS - Mateo Chukka Boot TOMS Mateo Chukka Boot $119.00 $82.99 Rated: 5 stars!
View More Like This SOREL - Madson Moc Toe SOREL Madson Moc Toe $190.00 Rated: 5 stars! View More Like This SOREL - Madson Moc Toe SOREL Madson Moc Toe $190.00 Rated: 5 stars! View More Like This SOREL - Madson Moc Toe SOREL Madson Moc Toe $190.00 Rated: 5 stars! View More Like This Chaco - Montrose Chukka Chaco Montrose Chukka $139.95 Rated: 5 stars!
View More Like This Chaco - Montrose Chukka Chaco Montrose Chukka $139.95 Rated: 5 stars! View More Like This Chaco - Montrose Chukka Chaco Montrose Chukka $139.95 Rated: 5 stars! View More Like This Sperry Top-Sider - A/O Lug Boat Chukka Waterproof Boot Sperry Top-Sider A/O Lug Boat Chukka Waterproof Boot $140.00 Rated: 5 stars! View More Like This Sperry Top-Sider - Dockyard Chukka Sperry Top-Sider Dockyard Chukka $150.00 Rated: 5 stars!
View More Like This Sperry Top-Sider - A/O Lug Boat Chukka Waterproof Boot Sperry Top-Sider A/O Lug Boat Chukka Waterproof Boot $140.00 Rated: 5 stars! View More Like This Sperry Top-Sider - Dockyard Chukka Sperry Top-Sider Dockyard Chukka $150.00 Rated: 5 stars! View More Like This Eastland 1955 Edition - Seneca Eastland 1955 Edition Seneca $110.00 Rated: 5 stars! View More Like This Eastland 1955 Edition - Seneca Eastland 1955 Edition Seneca $110.00 $98.99 Rated: 5 stars!
View More Like This Tommy Bahama - Fane Tommy Bahama Fane $198.00 $139.99 Rated: 5 stars! View More Like This UGG - Hendrickson UGG Hendrickson $129.95 Rated: 5 stars! View More Like This Rockport - Prestige Point Chukka Rockport Prestige Point Chukka $174.95 Rated: 5 stars! View More Like This ECCO - Jamestown Mid ECCO Jamestown Mid $190.00 $170.99 Rated: 5 stars!
View More Like This Tommy Bahama - Fane Tommy Bahama Fane $198.00 $139.99 Rated: 5 stars! View More Like This UGG - Hendrickson UGG Hendrickson $129.95 Rated: 5 stars! View More Like This Rockport - Prestige Point Chukka Rockport Prestige Point Chukka $174.95 Rated: 5 stars! View More Like This UGG - Hendrickson UGG Hendrickson $129.95 Rated: 5 stars!
View More Like This Wolverine - Cort Waterproof Leather Chukka Wolverine Cort Waterproof Leather Chukka $160.00 Rated: 5 stars! View More Like This Wolverine - Cort Waterproof Leather Chukka Wolverine Cort Waterproof Leather Chukka $160.00 Rated: 5 stars! View More Like This Rockport - Classic Break Chukka Rockport Classic Break Chukka $119.95 $109.95 Rated: 5 stars! View More Like This Rockport - Prestige Point Chukka Rockport Prestige Point Chukka $174.95 Rated: 5 stars!
View More Like This Rockport - Classic Break Chukka Rockport Classic Break Chukka $119.95 $109.95 Rated: 5 stars! View More Like This UGG - Neumel Donegal UGG Neumel Donegal $129.95 $87.07 Rated: 5 stars! View More Like This Rockport - Classic Break Chukka Rockport Classic Break Chukka $119.95 $109.95 Rated: 5 stars! View More Like This Trask - Gulch 2.0 Trask Gulch 2.0 $275.00 $192.99 Rated: 5 stars!
View More Like This Born - Neuman Born Neuman $115.00 $104.99 Rated: 5 stars! View More Like This Born - Neuman Born Neuman $115.00 $104.99 Rated: 5 stars! View More Like This Camper - Beetle Hi-36530 Camper Beetle Hi-36530 $195.00 Rated: 5 stars! View More Like This Camper - Beetle Hi-36530 Camper Beetle Hi-36530 $199.00 Rated: 5 stars!
View More Like This Sebago - Beacon Shearling Sebago Beacon Shearling $120.00 Rated: 5 stars! View More Like This Oliberte - Adibo Oliberte Adibo $120.00 Rated: 5 stars! View More Like This UGG - Hendrickson UGG Hendrickson $139.95 Rated: 5 stars! View More Like This Sebago - Beacon Shearling Sebago Beacon Shearling $120.00 Rated: 5 stars!
View More Like This Cole Haan - Zerogrand Stitchout Chukka Cole Haan Zerogrand Stitchout Chukka $280.00 Rated: 5 stars! View More Like This Cole Haan - Zerogrand Stitchout Chukka Cole Haan Zerogrand Stitchout Chukka $280.00 Rated: 5 stars! View More Like This Born - Fulton Born Fulton $130.00 $117.99 Rated: 5 stars! View More Like This Born - Fulton Born Fulton $130.00 $117.99 Rated: 5 stars!
View More Like This Dr. Martens - Maleke Padded Collar Boot Dr. Martens Maleke Padded Collar Boot $80.00 Rated: 5 stars! View More Like This Dr. Martens - Maleke Padded Collar Boot Dr. Martens Maleke Padded Collar Boot $80.00 Rated: 5 stars! View More Like This Sperry Top-Sider - Dockyard Chukka Sperry Top-Sider Dockyard Chukka $150.00 $104.99 Rated: 5 stars! View More Like This Dockers - Woodson Dockers Woodson $79.99 Rated: 5 stars!
View More Like This Dockers - Woodson Dockers Woodson $79.99 Rated: 5 stars! View More Like This Lacoste - Crosley Chukka 316 2 Lacoste Crosley Chukka 316 2 $244.95 $195.99 Rated: 5 stars! View More Like This Lacoste - Crosley Chukka 316 2 Lacoste Crosley Chukka 316 2 $244.95 $220.99 Rated: 5 stars! View More Like This Trask - Arlington Trask Arlington $275.00 $247.99 Rated: 5 stars!
View More Like This Trask - Arlington Trask Arlington $275.00 $192.99 Rated: 5 stars! View More Like This Ben Sherman - Antonio Lug Ben Sherman Antonio Lug $135.00 $94.99 Rated: 5 stars! View More Like This Ben Sherman - Antonio Lug Ben Sherman Antonio Lug $135.00 $94.99 Rated: 5 stars! View More Like This UGG - Maksim UGG Maksim $124.95 Rated: 5 stars!
View More Like This UGG - Maksim UGG Maksim $124.95 Rated: 5 stars! View More Like This UGG - Maksim UGG Maksim $124.95 Rated: 5 stars! NEW! View More Like This UGG - Maksim UGG Maksim $124.95 Rated: 5 stars! UGG - Maksim UGG Maksim $124.95 Rated: 5 stars!
View More Like This UGG - Maksim UGG Maksim $124.95 Rated: 5 stars! NEW! View More Like This UGG - Maksim UGG Maksim $124.95 Rated: 5 stars! NEW! View More Like This Lacoste - Sevrin Mid 416 1 Lacoste Sevrin Mid 416 1 $129.95 $90.99 Rated: 5 stars! View More Like This Irish Setter - Borderland Chukka Irish Setter Borderland Chukka $190.00 $169.95 Rated: 4 stars!