holiday-shipping

“chukka and Men Shoes” we found 880 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.

Clarks - Desert Boot Clarks Desert Boot $130.00 Rated: 5 stars! Born - Harrison Born Harrison $99.00 Rated: 4 stars! Rockport - Essential Details Waterproof Dress Chukka Rockport Essential Details Waterproof Dress Chukka $110.00 Rated: 4 stars! Clarks - Desert Boot Clarks Desert Boot $130.00 Rated: 5 stars!
Merrell - Realm Chukka Merrell Realm Chukka $150.00 Rated: 4 stars! Timberland - Earthkeepers® Brook Park Chukka Timberland Earthkeepers® Brook Park Chukka $130.00 Rated: 4 stars! Rockport - Ledge Hill 2 Chukka Boot Rockport Ledge Hill 2 Chukka Boot $150.00 Rated: 4 stars! Bed Stu - Draco Bed Stu Draco $135.00 Rated: 4 stars!
Keen - Tyretread Boot Keen Tyretread Boot $140.00 Rated: 4 stars! Clarks - Desert Boot Clarks Desert Boot $130.00 Rated: 5 stars! Timberland - Earthkeepers® City Lite Waterproof Chukka Timberland Earthkeepers® City Lite Waterproof Chukka $120.00 Rated: 4 stars! Timberland - Earthkeepers® City Lite Waterproof Chukka Timberland Earthkeepers® City Lite Waterproof Chukka $120.00 Rated: 4 stars!
UGG - Kaldwell UGG Kaldwell $139.95 Rated: 5 stars! Rockport - RocSports Lite 2 Chukka Rockport RocSports Lite 2 Chukka $120.00 Rated: 5 stars! Clarks - Stratton Limit Clarks Stratton Limit $135.00 Rated: 5 stars! Timberland - Earthkeepers® City Lite Chukka Timberland Earthkeepers® City Lite Chukka $100.00 Rated: 4 stars!
Timberland - Earthkeepers® Britton Hill Chukka Timberland Earthkeepers® Britton Hill Chukka $170.00 Rated: 4 stars! ECCO - Turn GTX Boot ECCO Turn GTX Boot $225.00 Rated: 5 stars! UGG - Neumel UGG Neumel $129.95 Rated: 4 stars! Rockport - RocSports Lite 2 Chukka Rockport RocSports Lite 2 Chukka $120.00 Rated: 5 stars!
Timberland - Earthkeepers® City Lite Chukka Timberland Earthkeepers® City Lite Chukka $100.00 Rated: 4 stars! Timberland - Earthkeepers® Brook Park Chukka Timberland Earthkeepers® Brook Park Chukka $130.00 Rated: 4 stars! Sperry Top-Sider - Dockyard Oxford Chukka Sperry Top-Sider Dockyard Oxford Chukka $125.00 Rated: 5 stars! UGG - Neumel UGG Neumel $129.95 Rated: 4 stars!
ECCO - Turn GTX Boot ECCO Turn GTX Boot $160.00 Rated: 5 stars! Nunn Bush - Woodbury Plain Toe Casual Chukka Boot Nunn Bush Woodbury Plain Toe Casual Chukka Boot $60.00 Rated: 5 stars! Florsheim - Rockit Chukka Boot Florsheim Rockit Chukka Boot $130.00 Rated: 5 stars! Dunham - Addison Dunham Addison $140.00 Rated: 4 stars!
UGG - Leighton UGG Leighton $159.95 Rated: 4 stars! ECCO - Turn GTX Boot ECCO Turn GTX Boot $225.00 Rated: 5 stars! Merrell - Himavat Chukka Waterproof Merrell Himavat Chukka Waterproof $175.00 Rated: 5 stars! Florsheim - Rockit Chukka Boot Florsheim Rockit Chukka Boot $130.00 Rated: 5 stars!
Clarks - Desert Boot Clarks Desert Boot $130.00 Rated: 5 stars! UGG - Neumel UGG Neumel $129.95 Rated: 4 stars! Rockport - RocSports Lite ZoneCush Plain Toe Boot Rockport RocSports Lite ZoneCush Plain Toe Boot $120.00 Rated: 4 stars! Rockport - RocSports Lite 2 Chukka Rockport RocSports Lite 2 Chukka $120.00 Rated: 5 stars!
UGG - Leighton UGG Leighton $159.95 Rated: 4 stars! Nunn Bush - Dodge Nunn Bush Dodge $68.00 Rated: 5 stars! Merrell - Himavat Chukka Waterproof Merrell Himavat Chukka Waterproof $175.00 Rated: 5 stars! Rockport - Trace Ridge Moc Boot Waterproof Rockport Trace Ridge Moc Boot Waterproof $120.00 Rated: 3 stars!
Clarks - Senner Ave Clarks Senner Ave $90.00 Rated: 4 stars! UGG - Leighton UGG Leighton $159.95 Rated: 4 stars! Rockport - City Smart - Waterproof Dress Chukka Boot Rockport City Smart - Waterproof Dress Chukka Boot $150.00 Rated: 3 stars! Dunham - Addison Dunham Addison $140.00 Rated: 4 stars!
Merrell - Realm Chukka Merrell Realm Chukka $150.00 Rated: 4 stars! Nunn Bush - Woodbury Plain Toe Casual Chukka Boot Nunn Bush Woodbury Plain Toe Casual Chukka Boot $60.00 Rated: 5 stars! Keen - Tyretread Boot Keen Tyretread Boot $140.00 Rated: 4 stars! Clarks - Senner Ave Clarks Senner Ave $90.00 Rated: 4 stars!
Rockport - RocSports Lite ZoneCush Plain Toe Boot Rockport RocSports Lite ZoneCush Plain Toe Boot $120.00 Rated: 4 stars! Sperry Top-Sider - Dockyard Sport Chukka Sperry Top-Sider Dockyard Sport Chukka $130.00 UGG - Leighton UGG Leighton $159.95 Rated: 4 stars! Nunn Bush - Woodbury Plain Toe Casual Chukka Boot Nunn Bush Woodbury Plain Toe Casual Chukka Boot $60.00 Rated: 5 stars!
UGG - Brompton Tweed UGG Brompton Tweed $194.95 Rockport - Essential Details Waterproof Dress Chukka Rockport Essential Details Waterproof Dress Chukka $110.00 Rated: 4 stars! Steve Madden - Hestonn Steve Madden Hestonn $85.00 Rated: 4 stars! UGG - Leighton UGG Leighton $159.95 Rated: 4 stars!
Clarks - Desert Boot Clarks Desert Boot $130.00 Rated: 5 stars! Timberland - Earthkeepers® Britton Hill Chukka Timberland Earthkeepers® Britton Hill Chukka $170.00 Rated: 4 stars! Bed Stu - Draco Bed Stu Draco $135.00 Rated: 4 stars! Steve Madden - Hestonn Steve Madden Hestonn $85.00 Rated: 4 stars!
SKECHERS - Mariner SKECHERS Mariner $69.00 Rated: 4 stars! Rockport - Rugged Bucks Waterproof Boot Rockport Rugged Bucks Waterproof Boot $120.00 Rated: 3 stars! UGG - Kaldwell UGG Kaldwell $139.95 Rated: 5 stars! Clarks - Wallabee Boot Clarks Wallabee Boot $140.00 Rated: 5 stars!
Rockport - Ledge Hill 2 Chukka Boot Rockport Ledge Hill 2 Chukka Boot $150.00 Rated: 4 stars! Born - Twain Born Twain $99.00 Rated: 4 stars! UGG - Leighton UGG Leighton $159.95 Rated: 4 stars! Clarks - Montacute Duke Clarks Montacute Duke $140.00 Rated: 5 stars!
ECCO - Dublin Plain Toe Tie Boot GTX ECCO Dublin Plain Toe Tie Boot GTX $200.00 Rated: 5 stars! UGG - Alin UGG Alin $149.95 Rated: 4 stars! Timberland - Earthkeepers® Britton Hill Chukka Timberland Earthkeepers® Britton Hill Chukka $170.00 Rated: 4 stars! UGG - Seton UGG Seton $199.95
Clarks - Novato Mid Clarks Novato Mid $130.00 Rated: 5 stars! Nunn Bush - Monona Nunn Bush Monona $76.00 Steve Madden - Harken Steve Madden Harken $85.00 Rated: 4 stars! Red Wing Heritage - Work Chukka Red Wing Heritage Work Chukka $260.00 Rated: 5 stars!
Dunham - REVdash Dunham REVdash $150.00 Polo Ralph Lauren - Waterton Polo Ralph Lauren Waterton $139.00 John Varvatos - Hipster Chukka John Varvatos Hipster Chukka $198.00 Rated: 4 stars! Red Wing Heritage - Blacksmith 6 Red Wing Heritage Blacksmith 6" Round Toe $300.00 Rated: 5 stars!
Rockport - Rocsports Lite - Es Waterproof Mocc Toe Mudguard Boot Rockport Rocsports Lite - Es Waterproof Mocc Toe Mudguard Boot $150.00 Rated: 3 stars! UGG - Kaldwell UGG Kaldwell $139.95 Rated: 5 stars! UGG - Lyle UGG Lyle $149.95 Rated: 5 stars! Rockport - RocSports Lite ZoneCush Plain Toe Boot Rockport RocSports Lite ZoneCush Plain Toe Boot $120.00 Rated: 4 stars!
Clarks - Desert Trek Clarks Desert Trek $120.00 Rated: 5 stars! UGG - Alin UGG Alin $149.95 Rated: 4 stars! ECCO - Edinburgh GTX Boot ECCO Edinburgh GTX Boot $180.00 UGG - Kaldwell UGG Kaldwell $139.95 Rated: 5 stars!
Clarks - Raspin Limit Clarks Raspin Limit $120.00 Clarks - Desert Boot Clarks Desert Boot $130.00 Rated: 5 stars! Timberland PRO - Five Star Wilshire Timberland PRO Five Star Wilshire $114.00 Rated: 5 stars! Rockport - RocSports Lite 2 Chukka Rockport RocSports Lite 2 Chukka $120.00 Rated: 5 stars!
Florsheim - Jet Chukka Boot Florsheim Jet Chukka Boot $135.00 Rated: 5 stars! UGG - Kaldwell UGG Kaldwell $139.95 Rated: 5 stars! Red Wing Heritage - Work Chukka Red Wing Heritage Work Chukka $260.00 Rated: 5 stars! SeaVees - 12/67 3 Eye Chukka SeaVees 12/67 3 Eye Chukka $178.00 Rated: 5 stars!
Vans - Mid Slip Vans Mid Slip $67.00 Rated: 3 stars! Vivobarefoot - Gobi II M Leather Vivobarefoot Gobi II M Leather $150.00 Rated: 4 stars! ECCO - Contoured Low Cut Boot ECCO Contoured Low Cut Boot $200.00 Rated: 5 stars! Timberland - Earthkeepers® Brook Park Chukka Timberland Earthkeepers® Brook Park Chukka $130.00 Rated: 4 stars!
Zappos Family Core Value:

10. Be Humble