Order Anytime, Free Shipping, Free Returns

“chukka and Men Boots” we found 100 items!

Choose a
  • Product Type
to sort results

We adjusted your search results to be more relevant. Not what you were looking for? Click here.

TOMS - Mateo Chukka Boot TOMS Mateo Chukka Boot $98.00 Rated: 5 stars! Dunham - Addison Dunham Addison $150.00 Rated: 4 stars! Rockport - RocSports Lite 2 Chukka Rockport RocSports Lite 2 Chukka $119.95 Rated: 4 stars! Clarks - Newkirk Top Clarks Newkirk Top $135.00 Rated: 5 stars!
Clarks - Hawkley Rise Clarks Hawkley Rise $125.00 Rated: 4 stars! TOMS - Chukka Boot TOMS Chukka Boot $129.00 Rated: 4 stars! Clarks - Newkirk Top Clarks Newkirk Top $135.00 Rated: 5 stars! Hush Puppies - Roland Jester Hush Puppies Roland Jester $139.00
Rockport - Total Motion Fusion Desert Boot Rockport Total Motion Fusion Desert Boot $150.00 Rated: 5 stars! Ben Sherman - Prill Chukka Ben Sherman Prill Chukka $65.00 Rated: 5 stars! Rockport - Rugged Bucks Moc Boot Waterproof Rockport Rugged Bucks Moc Boot Waterproof $119.95 Rated: 3 stars! Rockport - RocSports Lite 2 Chukka Rockport RocSports Lite 2 Chukka $119.95 Rated: 4 stars!
SKECHERS - Relaxed Fit Segment - Barillo SKECHERS Relaxed Fit Segment - Barillo $85.00 Rated: 5 stars! UGG - Freamon Capra UGG Freamon Capra $129.95 UGG - Leighton UGG Leighton $159.95 Rated: 4 stars! Wolverine - Cort Waterproof Leather Chukka Wolverine Cort Waterproof Leather Chukka $160.00 Rated: 5 stars!
Eastland 1955 Edition - Seneca Eastland 1955 Edition Seneca $100.00 Rated: 5 stars! ECCO - Turn GTX Boot ECCO Turn GTX Boot $230.00 Rated: 5 stars! Timberland - Earthkeepers® Brook Park Chukka Timberland Earthkeepers® Brook Park Chukka $110.00 Rated: 5 stars! Volcom - Del Mesa 2 Volcom Del Mesa 2 $85.00 $75.99 Rated: 4 stars!
TOMS - Mateo Chukka Boot TOMS Mateo Chukka Boot $98.00 Rated: 5 stars! Oliberte - Adibo Oliberte Adibo $130.00 Rated: 5 stars! Rockport - Total Motion Fusion Desert Boot Rockport Total Motion Fusion Desert Boot $150.00 Rated: 5 stars! Base London - Henry Base London Henry $148.00 Rated: 5 stars!
Merrell - Epiction Merrell Epiction $160.00 Rated: 5 stars! Wolverine - Cort Waterproof Leather Chukka Wolverine Cort Waterproof Leather Chukka $160.00 Rated: 5 stars! Timberland - Britton Hill Waterproof Chukka Timberland Britton Hill Waterproof Chukka $180.00 Rated: 5 stars! Sebago - Ryde Chukka Sebago Ryde Chukka $125.00 Rated: 4 stars!
Volcom - Del Mesa 2 Volcom Del Mesa 2 $120.00 $95.99 Rated: 4 stars! Base London - Henry Base London Henry $148.00 Rated: 5 stars! Irish Setter - Borderland Chukka Irish Setter Borderland Chukka $190.00 Rated: 4 stars! Dr. Martens - Sawyer Desert Boot Dr. Martens Sawyer Desert Boot $140.00 Rated: 5 stars!
Volcom - Del Mesa 2 Volcom Del Mesa 2 $85.00 $75.99 Rated: 4 stars! Dr. Martens - Sawyer Desert Boot Dr. Martens Sawyer Desert Boot $140.00 Rated: 5 stars! UGG - Neumel UGG Neumel $139.95 Rated: 4 stars! TOMS - Chukka Boot TOMS Chukka Boot $129.00 Rated: 4 stars!
ECCO - Jeremy Hybrid Boot ECCO Jeremy Hybrid Boot $210.00 Rated: 4 stars! Eastland 1955 Edition - Seneca Eastland 1955 Edition Seneca $100.00 Rated: 5 stars! Irish Setter - Borderland Chukka Irish Setter Borderland Chukka $179.99 Rated: 4 stars! Timberland - Groveton Plain Toe Chukka Leather and Fabric Timberland Groveton Plain Toe Chukka Leather and Fabric $90.00 Rated: 5 stars!
Chippewa - 5' Modern Suburban Boot Chippewa 5' Modern Suburban Boot $280.00 Volcom - Del Mesa 2 Volcom Del Mesa 2 $85.00 $67.99 Rated: 4 stars! Frye - James Bal Chukka Leather Frye James Bal Chukka Leather $348.00 Volcom - Del Mesa 2 Volcom Del Mesa 2 $85.00 $67.99 Rated: 4 stars!
Clarks - Chilver Hi GTX® Clarks Chilver Hi GTX® $160.00 Rated: 3 stars! Timberland - Groveton Moc Toe Chukka Timberland Groveton Moc Toe Chukka $100.00 Rated: 4 stars! Volcom - Del Mesa 2 Volcom Del Mesa 2 $85.00 Rated: 4 stars! TOMS - Mateo Chukka Boot TOMS Mateo Chukka Boot $139.00 Rated: 5 stars!
Rockport - Total Motion Fusion Desert Boot Rockport Total Motion Fusion Desert Boot $150.00 Rated: 5 stars! TOMS - Mateo Chukka Boot TOMS Mateo Chukka Boot $98.00 Rated: 5 stars! Base London - Roop Base London Roop $178.00 UGG - Freamon Capra UGG Freamon Capra $129.95
Jeffery-West - Laser Chukka Jeffery-West Laser Chukka $275.00 Eastland 1955 Edition - Seneca Eastland 1955 Edition Seneca $100.00 Rated: 5 stars! Wolverine - Francisco Chukka Wolverine Francisco Chukka $180.00 Rated: 5 stars! Frye - James Lug Chukka Frye James Lug Chukka $358.00 Rated: 5 stars!
OluKai - Pahoa OluKai Pahoa $200.00 Geox - U Mantra 7 Geox U Mantra 7 $160.00 Rated: 2 stars! Timberland - West Haven Chukka Timberland West Haven Chukka $160.00 Rated: 5 stars! Timberland - West Haven Chukka Timberland West Haven Chukka $160.00 Rated: 5 stars!
Woolrich - Beebe Leather Woolrich Beebe Leather $180.00 Rated: 5 stars! Volcom - Del Mesa 2 Volcom Del Mesa 2 $85.00 $67.99 Rated: 4 stars! Merrell - All Out Blazer Chukka Merrell All Out Blazer Chukka $130.00 Rated: 4 stars! Volcom - Salton Volcom Salton $90.00
Volcom - Del Mesa 2 Volcom Del Mesa 2 $85.00 Rated: 4 stars! Volcom - Del Mesa 2 Volcom Del Mesa 2 $85.00 Rated: 4 stars! TOMS - Brogue Boot TOMS Brogue Boot $179.00 Rated: 3 stars! Rockport - Total Motion Fusion Desert Boot Rockport Total Motion Fusion Desert Boot $150.00 Rated: 5 stars!
Mark Nason - Holford Mark Nason Holford $115.00 Oliberte - Adibo Oliberte Adibo $130.00 $104.99 Rated: 5 stars! Mark Nason - Holford Mark Nason Holford $115.00 Base London - Roop Base London Roop $178.00 $142.99
UGG - Hulman Perforated UGG Hulman Perforated $149.95 UGG - Hulman Perforated UGG Hulman Perforated $149.95 UGG - Hulman Perforated UGG Hulman Perforated $149.95 Merrell - All Out Blazer Chukka Merrell All Out Blazer Chukka $130.00 Rated: 4 stars!
Eastland 1955 Edition - Oneida 1955 Eastland 1955 Edition Oneida 1955 $155.00 Rated: 4 stars! Eastland 1955 Edition - Oneida 1955 Eastland 1955 Edition Oneida 1955 $155.00 Rated: 4 stars! Pikolinos - Glasgow 05M-6030F Pikolinos Glasgow 05M-6030F $200.00 Rated: 4 stars! Chippewa - 5' Modern Suburban Boot Chippewa 5' Modern Suburban Boot $280.00
Frye - James Bal Chukka Leather Frye James Bal Chukka Leather $348.00 Frye - Phillip Lug Wingtip Chukka Frye Phillip Lug Wingtip Chukka $398.00 UGG - Brompton UGG Brompton $194.95 Clarks - Chilver Hi GTX® Clarks Chilver Hi GTX® $160.00 Rated: 3 stars!
Frye - James Lug Chukka Shearling Frye James Lug Chukka Shearling $388.00 Rated: 5 stars! Frye - James Lug Chukka Shearling Frye James Lug Chukka Shearling $388.00 Rated: 5 stars! Frye - James Lug Chukka Shearling Frye James Lug Chukka Shearling $388.00 Rated: 5 stars! Pikolinos - Ellesmere M6C-8069 Pikolinos Ellesmere M6C-8069 $215.00 Rated: 5 stars!
Geox - MBRAYDEN2FITABX1 Geox MBRAYDEN2FITABX1 $210.00 Geox - MBRAYDEN2FITABX1 Geox MBRAYDEN2FITABX1 $210.00 Eastland 1955 Edition - Oneida 1955 Eastland 1955 Edition Oneida 1955 $155.00 Rated: 4 stars! Timberland - Groveton Moc Toe Chukka Timberland Groveton Moc Toe Chukka $100.00 Rated: 4 stars!
Volcom - Salton Volcom Salton $90.00 TOMS - Chukka Boot TOMS Chukka Boot $129.00 Rated: 4 stars! Hush Puppies - Roland Jester Hush Puppies Roland Jester $139.00 Oliberte - Adibo Oliberte Adibo $130.00 Rated: 5 stars!
UGG - Hulman Perforated UGG Hulman Perforated $149.95 UGG - Freamon Capra UGG Freamon Capra $129.95 UGG - Freamon Capra UGG Freamon Capra $129.95 Eastland 1955 Edition - Seneca Eastland 1955 Edition Seneca $100.00 Rated: 5 stars!
Zappos Family Core Value:

10. Be Humble