“chukka and Men Boots” we found 140 items!

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View More Like This Clarks - Newkirk Top Clarks Newkirk Top $135.00 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 - Rugged Bucks Moc Boot Waterproof Rockport Rugged Bucks Moc Boot Waterproof $119.95 $89.95 Rated: 3 stars! View More Like This Wolverine - Cort Waterproof Leather Chukka Wolverine Cort Waterproof Leather Chukka $160.00 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 ECCO - Turn GTX Boot ECCO Turn GTX Boot $230.00 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 Rockport - Classic Break Chukka Rockport Classic Break Chukka $119.95 $109.95 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 Sperry Top-Sider - Sojourn Duck Chukka Boot Sperry Top-Sider Sojourn Duck Chukka Boot $110.00 Rated: 4 stars!
View More Like This SOREL - Madson Chukka SOREL Madson Chukka $170.00 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 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 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 Timberland - Tenmile Chukka Timberland Tenmile Chukka $110.00 $99.99 Rated: 4 stars! View More Like This Born - Neuman Born Neuman $115.00 $104.99 Rated: 5 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 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 Sperry Top-Sider - Sojourn Duck Chukka Boot Sperry Top-Sider Sojourn Duck Chukka Boot $110.00 Rated: 4 stars!
View More Like This SOREL - Madson Moc Toe SOREL Madson Moc Toe $190.00 Rated: 5 stars! View More Like This Oliberte - Adibo Oliberte Adibo $120.00 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 UGG - Freamon Capra UGG Freamon Capra $149.95 Rated: 3 stars!
View More Like This Eastland 1955 Edition - Seneca Eastland 1955 Edition Seneca $110.00 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 $125.99 Rated: 5 stars! View More Like This ECCO - Jamestown Mid ECCO Jamestown Mid $190.00 $152.99 Rated: 5 stars! View More Like This Ben Sherman - Gaston Chukka Ben Sherman Gaston Chukka $125.00 $87.99
View More Like This SOREL - Madson Chukka SOREL Madson Chukka $170.00 Rated: 4 stars! View More Like This SOREL - Madson Moc Toe SOREL Madson Moc Toe $190.00 Rated: 5 stars! View More Like This UGG - Hendrickson UGG Hendrickson $129.95 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 UGG - Freamon Capra UGG Freamon Capra $149.95 Rated: 3 stars! View More Like This Eastland 1955 Edition - Seneca Eastland 1955 Edition Seneca $110.00 $98.99 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 Sperry Top-Sider - Gold Annapolis Boot Sperry Top-Sider Gold Annapolis Boot $225.00
View More Like This Calvin Klein - Jae Calvin Klein Jae $140.00 $94.99 View More Like This Wolverine - Francisco Chukka Wolverine Francisco Chukka $180.00 $125.99 Rated: 4 stars! View More Like This SKECHERS - Relaxed Fit Segment - Barillo SKECHERS Relaxed Fit Segment - Barillo $85.00 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 $112.99 Rated: 5 stars!
View More Like This Sebago - Turner Chukka Waterproof Sebago Turner Chukka Waterproof $135.00 Rated: 3 stars! View More Like This Cole Haan - Grand Tour Chukka Cole Haan Grand Tour Chukka $170.00 $119.99 Rated: 4 stars! View More Like This Ben Sherman - Luke Chukka Distressed Ben Sherman Luke Chukka Distressed $140.00 $112.99 View More Like This UGG - Freamon Capra UGG Freamon Capra $149.95 Rated: 3 stars!
View More Like This Hush Puppies - Roland Jester Hush Puppies Roland Jester $139.00 $125.99 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 Sperry Top-Sider - Clipper Chukka Sperry Top-Sider Clipper Chukka $120.00 View More Like This Sperry Top-Sider - A/O Mini Lug Chukka Sperry Top-Sider A/O Mini Lug Chukka $120.00
View More Like This Born - Neuman Born Neuman $115.00 $104.99 Rated: 5 stars! 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 Cole Haan - Grand Tour Chukka Cole Haan Grand Tour Chukka $170.00 $119.99 Rated: 4 stars!
View More Like This Lacoste - Laccord Chukka 117 1 Cam Lacoste Laccord Chukka 117 1 Cam $159.95 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 Frye - James Lug Chukka Shearling Frye James Lug Chukka Shearling $388.00 $310.40 Rated: 5 stars! View More Like This Birkenstock - Harris Birkenstock Harris $199.00 Rated: 4 stars!
View More Like This Calvin Klein - Jae Calvin Klein Jae $140.00 $94.99 View More Like This Ben Sherman - Gaston Chukka Ben Sherman Gaston Chukka $125.00 $87.99 View More Like This Ben Sherman - Antonio Lug Ben Sherman Antonio Lug $135.00 $94.99 Rated: 5 stars! View More Like This Merrell - Brevard Chukka Merrell Brevard Chukka $150.00 Rated: 2 stars!
View More Like This Sperry Top-Sider - Clipper Chukka Sperry Top-Sider Clipper Chukka $120.00 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 $170.99 View More Like This Trask - Arlington Trask Arlington $275.00 $247.99 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 Pikolinos - Glasgow 05M-6030F Pikolinos Glasgow 05M-6030F $200.00 Rated: 4 stars! View More Like This Eastland 1955 Edition - Seneca Eastland 1955 Edition Seneca $110.00 $98.99 Rated: 5 stars!
View More Like This El Naturalista - Yugen NG21 El Naturalista Yugen NG21 $159.90 $112.99 Rated: 4 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 Vivobarefoot - Gobi II M Leather Vivobarefoot Gobi II M Leather $150.00 Rated: 4 stars! View More Like This Trask - Irving Trask Irving $295.00 $265.99
View More Like This Ben Sherman - Antonio Lug Ben Sherman Antonio Lug $135.00 $94.99 Rated: 5 stars! View More Like This SOREL - Madson Moc Toe SOREL Madson Moc Toe $190.00 $132.99 Rated: 5 stars! View More Like This Sperry Top-Sider - A/O Mini Lug Chukka Sperry Top-Sider A/O Mini Lug Chukka $120.00 View More Like This Sperry Top-Sider - Clipper Chukka Sperry Top-Sider Clipper Chukka $120.00 $84.99
View More Like This Hush Puppies - Benson Rigby ICE+ Hush Puppies Benson Rigby ICE+ $180.00 Rated: 2 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 Justin - 235 Justin 235 $109.95 View More Like This Trask - Irving Trask Irving $295.00 $265.99
View More Like This Pikolinos - Glasgow 05M-6030F Pikolinos Glasgow 05M-6030F $200.00 $159.99 Rated: 4 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 Sperry Top-Sider - A/O Wedge Chukka Leather Sperry Top-Sider A/O Wedge Chukka Leather $120.00 View More Like This Eastland 1955 Edition - Seneca Eastland 1955 Edition Seneca $110.00 Rated: 5 stars!
View More Like This UGG - Hendrickson UGG Hendrickson $129.95 Rated: 5 stars! View More Like This Camper - 1913 Ankle Boot-36587 Camper 1913 Ankle Boot-36587 $195.00 $135.99 Rated: 1 stars! View More Like This Birkenstock - Harris Birkenstock Harris $199.00 Rated: 4 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 Pikolinos - Lugo M1F-8093 Pikolinos Lugo M1F-8093 $190.00 $152.99 View More Like This Lacoste - Crosley Chukka 316 2 Lacoste Crosley Chukka 316 2 $244.95 $170.99 Rated: 5 stars! View More Like This Trask - Arlington Trask Arlington $275.00 $192.99 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 Oliberte - Adibo Oliberte Adibo $120.00 Rated: 5 stars! View More Like This Merrell - Brevard Chukka Merrell Brevard Chukka $150.00 Rated: 2 stars! View More Like This Sperry Top-Sider - A/O Wedge Chukka Leather Sperry Top-Sider A/O Wedge Chukka Leather $120.00 View More Like This Sperry Top-Sider - Dockyard Chukka Sperry Top-Sider Dockyard Chukka $150.00 Rated: 5 stars!