“chukka and Men Boots” we found 183 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 TOMS - Mateo Chukka Boot TOMS Mateo Chukka Boot $98.00 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 Wolverine - Cort Waterproof Leather Chukka Wolverine Cort Waterproof Leather Chukka $160.00 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 Dunham - Addison Dunham Addison $150.00 Rated: 4 stars! View More Like This Timberland - Groveton Leather and Fabric Chukka Timberland Groveton Leather and Fabric Chukka $80.00 Rated: 5 stars! NEW!
View More Like This Rockport - Prestige Point Chukka Rockport Prestige Point Chukka $174.95 Rated: 5 stars! View More Like This Cole Haan - GrandPro Chukka Cole Haan GrandPro Chukka $150.00 $104.99 Rated: 5 stars! View More Like This ECCO - Turn GTX Boot ECCO Turn GTX Boot $230.00 Rated: 5 stars! View More Like This UGG - Neumel UGG Neumel $139.95 Rated: 4 stars!
View More Like This UGG - Neumel UGG Neumel $129.95 Rated: 4 stars! View More Like This TOMS - Chukka Boot TOMS Chukka Boot $129.00 $90.99 Rated: 4 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 UGG - Leighton UGG Leighton $159.95 Rated: 4 stars!
View More Like This Rockport - Prestige Point Chukka Rockport Prestige Point Chukka $174.95 Rated: 5 stars! View More Like This Cole Haan - GrandPro Chukka Cole Haan GrandPro Chukka $150.00 $104.99 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 TOMS - Mateo Chukka Boot TOMS Mateo Chukka Boot $119.00 $82.99 Rated: 5 stars!
View More Like This UGG - Leighton Bomber UGG Leighton Bomber $179.95 Rated: 4 stars! View More Like This Birkenstock - Harris Birkenstock Harris $199.00 $179.99 Rated: 4 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 Sperry Top-Sider - Dockyard Chukka Sperry Top-Sider Dockyard Chukka $150.00 $104.99 Rated: 5 stars!
View More Like This Rockport - Prestige Point Chukka Rockport Prestige Point Chukka $174.95 Rated: 5 stars! View More Like This SOREL - Ankeny™ Mid Hiker SOREL Ankeny™ Mid Hiker $135.00 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 UGG - Larken Stripe Perf UGG Larken Stripe Perf $169.95 NEW!
View More Like This Eastland 1955 Edition - Seneca Eastland 1955 Edition Seneca $110.00 $99.95 Rated: 5 stars! View More Like This Oliberte - Adibo Oliberte Adibo $120.00 Rated: 4 stars! View More Like This TOMS - Chukka Boot TOMS Chukka Boot $129.00 $90.99 Rated: 4 stars! View More Like This TOMS - Mateo Chukka Boot TOMS Mateo Chukka Boot $119.00 $95.99 Rated: 5 stars!
View More Like This Sperry Top-Sider - Dockyard Chukka Sperry Top-Sider Dockyard Chukka $150.00 $119.99 Rated: 5 stars! View More Like This UGG - Larken Stripe Perf UGG Larken Stripe Perf $169.95 NEW! View More Like This Wolverine - Francisco Chukka Wolverine Francisco Chukka $180.00 $144.99 Rated: 4 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 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 SOREL - Ankeny™ Mid Hiker SOREL Ankeny™ Mid Hiker $140.00 $112.99 Rated: 4 stars! View More Like This TOMS - Chukka Boot TOMS Chukka Boot $129.00 $90.99 Rated: 4 stars!
View More Like This TOMS - Mateo Chukka Boot TOMS Mateo Chukka Boot $98.00 Rated: 5 stars! View More Like This TOMS - Chukka Boot TOMS Chukka Boot $98.00 Rated: 4 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 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 - A/O Mini Lug Chukka Sperry Top-Sider A/O Mini Lug Chukka $120.00 $107.99 View More Like This UGG - Hendrickson UGG Hendrickson $129.95 $87.07 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 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 $196.00 Rated: 5 stars! View More Like This UGG - Freamon Capra UGG Freamon Capra $149.95 Rated: 3 stars! View More Like This Timberland - Westmore Leather Fabric Chukka Timberland Westmore Leather Fabric Chukka $149.95 View More Like This Volcom - Del Mesa 2 Volcom Del Mesa 2 $85.00 $75.99 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 El Naturalista - Yugen NG21 El Naturalista Yugen NG21 $159.90 $127.99 Rated: 4 stars! View More Like This Timberland - Groveton Leather and Fabric Chukka Timberland Groveton Leather and Fabric Chukka $80.00 Rated: 5 stars! NEW! View More Like This SOREL - Ankeny™ Mid Hiker SOREL Ankeny™ Mid Hiker $135.00 Rated: 4 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 Sperry Top-Sider - A/O Mini Lug Chukka Sperry Top-Sider A/O Mini Lug Chukka $120.00 $107.99 View More Like This UGG - Freamon Capra UGG Freamon Capra $149.95 Rated: 3 stars! View More Like This Merrell - Freewheel Mesh Chukka Merrell Freewheel Mesh Chukka $100.00
View More Like This Merrell - Freewheel Mesh Chukka Merrell Freewheel Mesh Chukka $100.00 View More Like This Cole Haan - GrandPro Chukka Cole Haan GrandPro Chukka $150.00 $104.99 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 Ben Sherman - Gaston Chukka Ben Sherman Gaston Chukka $125.00 $87.99 Rated: 3 stars!
View More Like This UGG - Maksim UGG Maksim $124.95 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 Sperry Top-Sider - Clipper Chukka Sperry Top-Sider Clipper Chukka $120.00 View More Like This Camper - 1913 Ankle Boot-36587 Camper 1913 Ankle Boot-36587 $195.00 $155.99 Rated: 1 stars!
View More Like This Ben Sherman - Antonio Lug Ben Sherman Antonio Lug $135.00 $94.99 Rated: 5 stars! View More Like This TOMS - Mateo Chukka Boot TOMS Mateo Chukka Boot $98.00 Rated: 5 stars! View More Like This UGG - Hendrickson Capra UGG Hendrickson Capra $159.95 NEW! 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 - Groveton Plain Toe Chukka Leather and Fabric Timberland Groveton Plain Toe Chukka Leather and Fabric $90.00 Rated: 5 stars! View More Like This Chaco - Montrose Chukka Chaco Montrose Chukka $139.95 Rated: 5 stars! View More Like This Birkenstock - Harris Birkenstock Harris $199.00 $179.99 Rated: 4 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 Cole Haan - Zerogrand Stitchout Chukka Cole Haan Zerogrand Stitchout Chukka $280.00 $196.00 Rated: 5 stars! View More Like This Rieker - F1310 Rieker F1310 $150.00 View More Like This Base London - Morris Base London Morris $140.00 NEW!
View More Like This Eastland 1955 Edition - Seneca Eastland 1955 Edition Seneca $110.00 $99.95 Rated: 5 stars! View More Like This Naot Footwear - Pilot - Hand Crafted Naot Footwear Pilot - Hand Crafted $240.00 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 Eastland 1955 Edition - Seneca Eastland 1955 Edition Seneca $110.00 $99.95 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 Ben Sherman - Gaston Chukka Ben Sherman Gaston Chukka $125.00 $112.99 Rated: 3 stars! View More Like This UGG - Larken Stripe Perf UGG Larken Stripe Perf $169.95 NEW! View More Like This Merrell - Freewheel Mesh Chukka Merrell Freewheel Mesh Chukka $100.00
View More Like This Timberland - Westmore Leather Fabric Chukka Timberland Westmore Leather Fabric Chukka $149.95 View More Like This Dr. Martens - Sawyer Desert Boot Dr. Martens Sawyer Desert Boot $130.00 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 Pikolinos - Glasgow 05M-6030F Pikolinos Glasgow 05M-6030F $200.00 Rated: 4 stars!
View More Like This Chaco - Montrose Chukka Chaco Montrose Chukka $139.95 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 Ben Sherman - Luke Chukka Distressed Ben Sherman Luke Chukka Distressed $140.00 $97.99 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 OluKai - Pahoa OluKai Pahoa $200.00 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 Josef Seibel - Oscar 11 Josef Seibel Oscar 11 $185.00 Rated: 5 stars!