“chukka and Men Boots” we found 137 items!

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View More Like This Rockport - Classic Break Chukka Rockport Classic Break Chukka $119.95 $109.95 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 Rockport - Rugged Bucks Moc Boot Waterproof Rockport Rugged Bucks Moc Boot Waterproof $119.95 $89.95 Rated: 3 stars! View More Like This TOMS - Mateo Chukka Boot TOMS Mateo Chukka Boot $98.00 Rated: 5 stars!
View More Like This UGG - Leighton UGG Leighton $159.95 Rated: 4 stars! View More Like This Dunham - Addison Dunham Addison $150.00 Rated: 4 stars! View More Like This SOREL - Madson Chukka SOREL Madson Chukka $170.00 Rated: 4 stars! View More Like This ECCO - Turn GTX Boot ECCO Turn GTX Boot $230.00 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 Timberland - Britton Hill Waterproof Chukka Timberland Britton Hill Waterproof Chukka $180.00 $162.99 Rated: 5 stars! View More Like This UGG - Leighton Bomber UGG Leighton Bomber $179.95 Rated: 2 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 Rockport - Classic Break Chukka Rockport Classic Break Chukka $119.95 $109.95 Rated: 5 stars! View More Like This Timberland - Carter Notch Waterproof Plain Toe Chukka Timberland Carter Notch Waterproof Plain Toe Chukka $140.00 Rated: 3 stars! View More Like This Sperry Top-Sider - Sojourn Duck Chukka Boot Sperry Top-Sider Sojourn Duck Chukka Boot $110.00 Rated: 4 stars! View More Like This Rockport - Prestige Point Chukka Rockport Prestige Point Chukka $174.95 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 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 Sperry Top-Sider - Sojourn Duck Chukka Boot Sperry Top-Sider Sojourn Duck Chukka Boot $110.00 Rated: 4 stars!
View More Like This Wolverine - Cort Waterproof Leather Chukka Wolverine Cort Waterproof Leather Chukka $160.00 Rated: 5 stars! View More Like This Sperry Top-Sider - Sojourn Duck Chukka Boot Sperry Top-Sider Sojourn Duck Chukka Boot $110.00 Rated: 4 stars! View More Like This SOREL - Ankeny™ Mid Hiker SOREL Ankeny™ Mid Hiker $135.00 Rated: 4 stars! View More Like This Rockport - Prestige Point Chukka Rockport Prestige Point Chukka $174.95 Rated: 5 stars!
View More Like This TOMS - Mateo Chukka Boot TOMS Mateo Chukka Boot $98.00 Rated: 5 stars! View More Like This Timberland - West Haven Chukka Timberland West Haven Chukka $160.00 $127.99 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 - Urban Retreat Desert Boot Rockport Urban Retreat Desert Boot $140.00 Rated: 3 stars!
View More Like This Merrell - Epiction Merrell Epiction $159.95 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 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 Timberland - Tenmile Chukka Timberland Tenmile Chukka $110.00 $99.99 Rated: 4 stars! View More Like This Sperry Top-Sider - Fowl Weather Chukka Sperry Top-Sider Fowl Weather Chukka $90.00 Rated: 4 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 SOREL - Madson Chukka SOREL Madson Chukka $170.00 Rated: 4 stars!
View More Like This Cole Haan - Zerogrand Stitchout Chukka Cole Haan Zerogrand Stitchout Chukka $280.00 Rated: 5 stars! View More Like This Ben Sherman - Luke Chukka Distressed Ben Sherman Luke Chukka Distressed $140.00 $125.99 View More Like This UGG - Freamon Capra UGG Freamon Capra $149.95 Rated: 3 stars! NEW! View More Like This Volcom - Del Mesa 2 Volcom Del Mesa 2 $120.00 $95.99 Rated: 5 stars!
View More Like This SOREL - Ankeny™ Mid Hiker SOREL Ankeny™ Mid Hiker $140.00 Rated: 4 stars! View More Like This Chaco - Montrose Chukka Chaco Montrose Chukka $139.95 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 Cole Haan - Grand Tour Chukka Cole Haan Grand Tour Chukka $170.00 $135.99 Rated: 4 stars! View More Like This Cole Haan - GrandPro Chukka Cole Haan GrandPro Chukka $150.00 $104.99 View More Like This Calvin Klein - Jae Calvin Klein Jae $140.00 $94.99 View More Like This Cole Haan - GrandPro Chukka Cole Haan GrandPro Chukka $150.00 $104.99
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 Hush Puppies - Roland Jester Hush Puppies Roland Jester $139.00 $110.99 Rated: 4 stars! View More Like This Chaco - Montrose Chukka Chaco Montrose Chukka $139.95 Rated: 5 stars!
View More Like This The North Face - Ballard EVO Chukka FG The North Face Ballard EVO Chukka FG $110.00 Rated: 3 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 - Clipper Chukka Sperry Top-Sider Clipper Chukka $120.00 View More Like This Cole Haan - Grand Tour Chukka Cole Haan Grand Tour Chukka $170.00 $119.99 Rated: 4 stars!
View More Like This Ben Sherman - Gaston Chukka Ben Sherman Gaston Chukka $125.00 $87.99 View More Like This UGG - Freamon Capra UGG Freamon Capra $149.95 Rated: 3 stars! NEW! View More Like This Sperry Top-Sider - Gold Annapolis Boot Sperry Top-Sider Gold Annapolis Boot $225.00 View More Like This Sperry Top-Sider - Clipper Chukka Sperry Top-Sider Clipper Chukka $120.00 $84.99
View More Like This Calvin Klein - Jae Calvin Klein Jae $140.00 $97.99 View More Like This Cole Haan - Zerogrand Stitchout Chukka Cole Haan Zerogrand Stitchout Chukka $280.00 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 Sebago - Turner Chukka Waterproof Sebago Turner Chukka Waterproof $135.00 Rated: 3 stars!
View More Like This Sebago - Beacon Shearling Sebago Beacon Shearling $120.00 Rated: 5 stars! View More Like This Wolverine - Francisco Chukka Wolverine Francisco Chukka $180.00 Rated: 4 stars! View More Like This TOMS - Mateo Chukka Boot TOMS Mateo Chukka Boot $119.00 $82.99 Rated: 5 stars! View More Like This Calvin Klein - Jae Calvin Klein Jae $140.00 $94.99
View More Like This Merrell - Freewheel Mesh Chukka Merrell Freewheel Mesh Chukka $100.00 View More Like This UGG - Freamon Capra UGG Freamon Capra $149.95 Rated: 3 stars! NEW! View More Like This Lacoste - Laccord Chukka 117 1 Cam Lacoste Laccord Chukka 117 1 Cam $159.95 NEW! View More Like This SOREL - Madson Moc Toe SOREL Madson Moc Toe $190.00 Rated: 5 stars!
View More Like This Sperry Top-Sider - Clipper Chukka Sperry Top-Sider Clipper Chukka $120.00 View More Like This Hush Puppies - Benson Rigby ICE+ Hush Puppies Benson Rigby ICE+ $180.00 Rated: 2 stars! View More Like This Ben Sherman - Gaston Chukka Ben Sherman Gaston Chukka $125.00 $87.99 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 Volcom - Del Mesa 2 Volcom Del Mesa 2 $85.00 $67.99 Rated: 5 stars! View More Like This Merrell - Brevard Chukka Merrell Brevard Chukka $150.00 Rated: 2 stars! View More Like This Sebago - Turner Chukka Waterproof Sebago Turner Chukka Waterproof $135.00 Rated: 3 stars! View More Like This Pikolinos - Lugo M1F-8093 Pikolinos Lugo M1F-8093 $190.00 $152.99
View More Like This El Naturalista - Yugen NG21 El Naturalista Yugen NG21 $159.90 $112.99 Rated: 4 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 - Freamon Canvas UGG Freamon Canvas $109.95 NEW! View More Like This Merrell - Freewheel Mesh Chukka Merrell Freewheel Mesh Chukka $100.00
View More Like This Ben Sherman - Devon Chukka Ben Sherman Devon Chukka $100.00 $69.99 View More Like This Cole Haan - GrandPro Chukka Cole Haan GrandPro Chukka $150.00 $104.99 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 Vivobarefoot - Gobi II M Leather Vivobarefoot Gobi II M Leather $150.00 Rated: 4 stars!
View More Like This Timberland - Earthkeepers® Brook Park Chukka Timberland Earthkeepers® Brook Park Chukka $110.00 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 Merrell - Brevard Chukka Merrell Brevard Chukka $150.00 Rated: 2 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 Stacy Adams - Delaney Chukka Boot Stacy Adams Delaney Chukka Boot $105.00 $74.99 Rated: 4 stars! View More Like This UGG - Freamon Canvas UGG Freamon Canvas $109.95 NEW! View More Like This Pikolinos - Glasgow 05M-6030F Pikolinos Glasgow 05M-6030F $200.00 $139.99 Rated: 4 stars!
View More Like This Pikolinos - Ellesmere M6C-8069 Pikolinos Ellesmere M6C-8069 $215.00 $150.99 Rated: 5 stars! View More Like This BOSS Hugo Boss - Pariss Desb by HUGO BOSS Hugo Boss Pariss Desb by HUGO $275.00 Rated: 4 stars! View More Like This TOMS - Mateo Chukka Boot TOMS Mateo Chukka Boot $129.00 $90.99 Rated: 5 stars! View More Like This Calvin Klein - Jae Calvin Klein Jae $140.00 $97.99