No Way! Free Next Day Shipping On Clothing M-F. Order Today, Wear It Tomorrow! Plus Free Returns. Learn More

“chukka and Men Boots” we found 110 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.

DSQUARED2 - Runway Construction Ankle Boot DSQUARED2 Runway Construction Ankle Boot $1,095.00 NEW! Tommy Bahama - Elijah Tommy Bahama Elijah $198.00 NEW! Tommy Bahama - Elijah Tommy Bahama Elijah $198.00 NEW! Sperry Top-Sider - Harbor Chukka Boot Sperry Top-Sider Harbor Chukka Boot $120.00 NEW!
Tommy Bahama - Riker Tommy Bahama Riker $138.00 NEW! Tommy Bahama - Riker Tommy Bahama Riker $138.00 NEW! Pikolinos - Cork 07S-6811 Pikolinos Cork 07S-6811 $210.00 NEW! Pikolinos - Cork 07S-6811 Pikolinos Cork 07S-6811 $210.00 NEW!
Pikolinos - Seoul 00T-6860 Pikolinos Seoul 00T-6860 $210.00 NEW! DSQUARED2 - Runway Construction Ankle Boot DSQUARED2 Runway Construction Ankle Boot $1,095.00 NEW! Rockport - RocSports Lite 2 Chukka Rockport RocSports Lite 2 Chukka $120.00 Rated: 5 stars! ECCO - Turn GTX Boot ECCO Turn GTX Boot $160.00 Rated: 5 stars!
ECCO - Turn GTX Boot ECCO Turn GTX Boot $225.00 Rated: 5 stars! UGG - Neumel UGG Neumel $129.95 Rated: 4 stars! Sperry Top-Sider - Dockyard Oxford Chukka Sperry Top-Sider Dockyard Oxford Chukka $125.00 Rated: 5 stars! Born - Twain Born Twain $119.00 Rated: 4 stars!
Dunham - Ryan Dunham Ryan $135.00 Wolverine - Francisco Chukka Wolverine Francisco Chukka $175.00 Rated: 5 stars! Polo Ralph Lauren - Torrington Chukka Polo Ralph Lauren Torrington Chukka $139.00 Rated: 5 stars! Rockport - Rocsports Lite - Es H20 Mocc Toe Mudguard Boot Rockport Rocsports Lite - Es H20 Mocc Toe Mudguard Boot $150.00
Born - Twain Born Twain $99.00 Rated: 4 stars! SKECHERS - Superior Relaxed Fit Chukka 2 SKECHERS Superior Relaxed Fit Chukka 2 $79.95 UGG - Neumel UGG Neumel $129.95 Rated: 4 stars! Ben Sherman - Vince - Chukka Ben Sherman Vince - Chukka $80.00
Rockport - Trace Ridge Moc Boot Waterproof Rockport Trace Ridge Moc Boot Waterproof $120.00 Rated: 3 stars! Cushe - Prospector Cushe Prospector $115.00 Rated: 4 stars! ECCO - Edinburgh GTX Boot ECCO Edinburgh GTX Boot $180.00 ECCO - Findlay Chukka Boot ECCO Findlay Chukka Boot $210.00
Merrell - Himavat Chukka Waterproof Merrell Himavat Chukka Waterproof $175.00 Rated: 5 stars! ECCO - Findlay Chukka Boot ECCO Findlay Chukka Boot $210.00 Ben Sherman - Vince - Chukka Ben Sherman Vince - Chukka $80.00 Ben Sherman - Vince - Chukka Ben Sherman Vince - Chukka $80.00
SKECHERS - Volte Herick SKECHERS Volte Herick $85.00 Ben Sherman - Vince - Chukka Ben Sherman Vince - Chukka $80.00 Ahnu - Harris Ahnu Harris $134.95 Rated: 4 stars! Caterpillar - Lear Caterpillar Lear $95.00
Pikolinos - Glasgow 05M-6030F Pikolinos Glasgow 05M-6030F $200.00 Rated: 5 stars! Merrell - Himavat Chukka Waterproof Merrell Himavat Chukka Waterproof $175.00 Rated: 5 stars! Volcom - Del Mesa Volcom Del Mesa $80.00 Volcom - Del Mesa Volcom Del Mesa $80.00
Wolverine - Francisco Chukka Wolverine Francisco Chukka $175.00 Rated: 5 stars! Born - Asten Born Asten $105.00 Rated: 3 stars! Born - Asten Born Asten $105.00 Rated: 3 stars! Sperry Top-Sider - Dockyard Oxford Chukka Sperry Top-Sider Dockyard Oxford Chukka $125.00 Rated: 5 stars!
Polo Ralph Lauren - Torrington Chukka Polo Ralph Lauren Torrington Chukka $139.00 Rated: 5 stars! UGG - Alin UGG Alin $149.95 Rated: 4 stars! UGG - Alin UGG Alin $149.95 Rated: 4 stars! The North Face - Base Camp Leather Chukka The North Face Base Camp Leather Chukka $100.00 Rated: 5 stars!
Cushe - Prospector Cushe Prospector $115.00 Rated: 4 stars! Wolverine - Karl Moc-Toe Chukka Wolverine Karl Moc-Toe Chukka $86.00 Rated: 5 stars! ECCO - Contoured Low Cut Boot ECCO Contoured Low Cut Boot $200.00 Rated: 5 stars! Sperry Top-Sider - Harbor Chukka Boot Sperry Top-Sider Harbor Chukka Boot $120.00
PF Flyers - Hi Pres PF Flyers Hi Pres $120.00 Marc New York by Andrew Marc - Dorchester Ckukka Marc New York by Andrew Marc Dorchester Ckukka $178.00 UGG - Alin UGG Alin $149.95 Rated: 4 stars! Hush Puppies - Aquaice Wallaboot Hush Puppies Aquaice Wallaboot $115.00
Bogs - Eugene Chukka Bogs Eugene Chukka $125.00 Patagonia - Whane Patagonia Whane $130.00 Rated: 5 stars! Camper - Motel-36724 Camper Motel-36724 $145.00 The North Face - Base Camp Leather Chukka The North Face Base Camp Leather Chukka $100.00 Rated: 5 stars!
Geox - U Jheryx B Abx 1 Geox U Jheryx B Abx 1 $220.00 Pikolinos - Glasgow 05M-6030F Pikolinos Glasgow 05M-6030F $200.00 Rated: 5 stars! Tommy Bahama - Rivington Tommy Bahama Rivington $138.00 Hush Puppies - Aquaice Wallaboot Hush Puppies Aquaice Wallaboot $115.00
Armani Jeans - Layered Sole Chukka Boot Armani Jeans Layered Sole Chukka Boot $230.00 Armani Jeans - Layered Sole Chukka Boot Armani Jeans Layered Sole Chukka Boot $230.00 Lacoste - Sherbrooke H Lacoste Sherbrooke H $160.00 Rated: 5 stars! Justin - 942 Justin 942 $115.00
Irish Setter - Borderland Chukka Irish Setter Borderland Chukka $179.99 Rated: 4 stars! Irish Setter - Borderland Chukka Irish Setter Borderland Chukka $179.99 Rated: 4 stars! Bogs - Eugene Chukka Bogs Eugene Chukka $125.00 SKECHERS - Superior Relaxed Fit Chukka 2 SKECHERS Superior Relaxed Fit Chukka 2 $79.95
Sebago - Halyard Chukka Sebago Halyard Chukka $185.00 Geox - U Jheryx B Abx 1 Geox U Jheryx B Abx 1 $220.00 Lacoste - Sherbrooke H Lacoste Sherbrooke H $160.00 Rated: 5 stars! Marc New York by Andrew Marc - Dorchester Ckukka Marc New York by Andrew Marc Dorchester Ckukka $178.00
Cycleur de Luxe - Allrounder Cycleur de Luxe Allrounder $170.00 Cushe - Prospector Cushe Prospector $115.00 Rated: 4 stars! Hush Puppies - Aquaice Wallaboot Hush Puppies Aquaice Wallaboot $115.00 Camper - Motel-36724 Camper Motel-36724 $155.00
UGG - Brompton UGG Brompton $194.95 Tommy Bahama - Edisto Tommy Bahama Edisto $198.00 Rated: 3 stars! Josef Seibel - Nolan 14 Josef Seibel Nolan 14 $170.00 Patagonia - Whane Patagonia Whane $130.00 Rated: 5 stars!
The North Face - Base Camp Leather Chukka The North Face Base Camp Leather Chukka $100.00 Rated: 5 stars! PF Flyers - Hi Pres PF Flyers Hi Pres $120.00 Pikolinos - Soria 03S-6751 Pikolinos Soria 03S-6751 $210.00 Tommy Bahama - Edisto Tommy Bahama Edisto $198.00 Rated: 3 stars!
Tommy Bahama - Rivington Tommy Bahama Rivington $138.00 Polo Ralph Lauren - Torrington Chukka NT Polo Ralph Lauren Torrington Chukka NT $139.00 Vivobarefoot - Soul Of Africa Gobi Vivobarefoot Soul Of Africa Gobi $160.00 Rated: 4 stars! Tommy Bahama - Edisto Tommy Bahama Edisto $198.00 Rated: 3 stars!
Polo Ralph Lauren - Barrott Polo Ralph Lauren Barrott $125.00 Rated: 1 stars! El Naturalista - Andaluz N647 El Naturalista Andaluz N647 $199.90 Mephisto - Walfred Mephisto Walfred $439.00 Bogs - Eugene Chukka Bogs Eugene Chukka $125.00
Quiksilver - Marquez Quiksilver Marquez $110.00 Polo Ralph Lauren - Barrott Polo Ralph Lauren Barrott $125.00 Rated: 1 stars! Irish Setter - 83612 6 Irish Setter 83612 6" Steel Toe Hiker $114.99 Rated: 5 stars! GUESS - Vargo GUESS Vargo $98.00
Zappos Family Core Value:

10. Be Humble