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 95 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.

Rockport - Ledge Hill 2 Chukka Boot Rockport Ledge Hill 2 Chukka Boot $150.00 Rated: 4 stars! Rockport - City Smart - H20 Dress Chukka Boot Rockport City Smart - H20 Dress Chukka Boot $150.00 Wolverine - Francisco Chukka Wolverine Francisco Chukka $175.00 Rated: 5 stars! Dr. Martens - Barnie Chukka Boot Dr. Martens Barnie Chukka Boot $120.00 Rated: 4 stars!
ECCO - Dublin Plain Toe Tie Boot GTX ECCO Dublin Plain Toe Tie Boot GTX $200.00 Rated: 5 stars! Cole Haan - Glenn Chukka Cole Haan Glenn Chukka $228.00 UGG - Brompton Tweed UGG Brompton Tweed $194.95 Cole Haan - Lunargrand Moc Chuk Cole Haan Lunargrand Moc Chuk $228.00
Clarks - Fawley Hi GTX Clarks Fawley Hi GTX $140.00 NEW! Nunn Bush - Monona Nunn Bush Monona $76.00 NEW! Ted Baker - Torsdi 2 Ted Baker Torsdi 2 $210.00 Cole Haan - Glenn Chukka Cole Haan Glenn Chukka $228.00
Rockport - Ledge Hill 2 Chukka Boot Rockport Ledge Hill 2 Chukka Boot $150.00 Rated: 4 stars! Frye - Oliver Chukka Frye Oliver Chukka $258.00 Rated: 4 stars! Ted Baker - Torsdi 2 Ted Baker Torsdi 2 $210.00 ECCO - Edinburgh GTX Boot ECCO Edinburgh GTX Boot $180.00
Wolverine - Orville Desert Boot Wolverine Orville Desert Boot $155.00 Cole Haan - Cambridge Chukka Cole Haan Cambridge Chukka $268.00 Cole Haan - Copley Chukka Boot Cole Haan Copley Chukka Boot $168.00 Rated: 4 stars! Steve Madden - Boro Steve Madden Boro $130.00
Ben Sherman - Bailey Ben Sherman Bailey $130.00 NEW! Fitzwell - Charles Fitzwell Charles $109.00 NEW! Frye - James Chukka Frye James Chukka $258.00 Rated: 4 stars! To Boot New York - Stallworth To Boot New York Stallworth $450.00 Rated: 5 stars!
Wolverine - Orville Desert Boot Wolverine Orville Desert Boot $155.00 Steve Madden - Hillside Steve Madden Hillside $110.00 Cole Haan - Cambridge Chukka Cole Haan Cambridge Chukka $268.00 Steve Madden - Garisonn Steve Madden Garisonn $110.00
Cole Haan - Copley Chukka Boot Cole Haan Copley Chukka Boot $168.00 Rated: 4 stars! Ben Sherman - Bailey Ben Sherman Bailey $130.00 NEW! Ben Sherman - Bailey Ben Sherman Bailey $130.00 NEW! Frye - Oliver Chukka Frye Oliver Chukka $258.00 Rated: 4 stars!
Steve Madden - Garisonn Steve Madden Garisonn $110.00 Frye - James Chukka Frye James Chukka $258.00 Rated: 4 stars! Wolverine - Francisco Chukka Wolverine Francisco Chukka $175.00 Rated: 5 stars! Armani Jeans - Layered Sole Chukka Boot Armani Jeans Layered Sole Chukka Boot $230.00
Clarks - Fawley Hi GTX Clarks Fawley Hi GTX $140.00 NEW! Donald J Pliner - Bishop Donald J Pliner Bishop $240.00 NEW! Trask - Gary Trask Gary $275.00 NEW! Call it SPRING - Wilbehrt Call it SPRING Wilbehrt $109.99
Call it SPRING - Wilbehrt Call it SPRING Wilbehrt $109.99 Frye - James Chukka Frye James Chukka $268.00 Rated: 4 stars! Steve Madden - Hillside Steve Madden Hillside $110.00 Armani Jeans - Layered Sole Chukka Boot Armani Jeans Layered Sole Chukka Boot $230.00
Cole Haan - Copley Chukka Boot Cole Haan Copley Chukka Boot $168.00 Rated: 4 stars! Sebago - Halyard Chukka Sebago Halyard Chukka $185.00 To Boot New York - Hunter To Boot New York Hunter $350.00 Trask - Gary Trask Gary $275.00 NEW!
Frye - Oliver Chukka Frye Oliver Chukka $258.00 Rated: 4 stars! Original Penguin - Chukka Original Penguin Chukka $180.00 Cole Haan - Glenn Chukka Cole Haan Glenn Chukka $228.00 To Boot New York - Cornell To Boot New York Cornell $398.00
To Boot New York - Newcomb To Boot New York Newcomb $395.00 Trask - Brady Trask Brady $265.00 NEW! Call it SPRING - Wilbehrt Call it SPRING Wilbehrt $109.99 Frye - Oliver Chukka Frye Oliver Chukka $258.00 Rated: 4 stars!
Frye - James Chukka Frye James Chukka $268.00 Rated: 4 stars! Frye - Oliver Chukka Frye Oliver Chukka $258.00 Rated: 4 stars! Cole Haan - Lunargrand Chukka Cole Haan Lunargrand Chukka $278.00 Rated: 5 stars! Cole Haan - Lunargrand Chukka Cole Haan Lunargrand Chukka $278.00 Rated: 5 stars!
Cole Haan - Lunargrand Moc Chuk Cole Haan Lunargrand Moc Chuk $228.00 Original Penguin - Chukka Original Penguin Chukka $180.00 Naot Footwear - Pilot Naot Footwear Pilot $199.00 Rated: 4 stars! Steve Madden - Garisonn Steve Madden Garisonn $110.00
Donald J Pliner - Bishop Donald J Pliner Bishop $240.00 NEW! Tommy Hilfiger - Holbrook Tommy Hilfiger Holbrook $140.00 Wolverine - Orville Desert Boot Wolverine Orville Desert Boot $155.00 Camper - Bowie-36717 Camper Bowie-36717 $199.00
To Boot New York - Antonio To Boot New York Antonio $350.00 To Boot New York - Horst To Boot New York Horst $350.00 Steve Madden - Boro Steve Madden Boro $130.00 Donald J Pliner - Bishop Donald J Pliner Bishop $240.00 NEW!
To Boot New York - Newcomb To Boot New York Newcomb $395.00 Calvin Klein Jeans - Tezer Calvin Klein Jeans Tezer $130.00 Mezlan - Grassi Mezlan Grassi $355.00 NEW! J. Shoes - Monarch J. Shoes Monarch $198.00
Frye - Oliver Chukka Frye Oliver Chukka $258.00 Rated: 4 stars! Trask - Brady Trask Brady $265.00 Cole Haan - Lunargrand Moc Chuk Cole Haan Lunargrand Moc Chuk $228.00 To Boot New York - Hunter To Boot New York Hunter $350.00
Calvin Klein Jeans - Tezer Calvin Klein Jeans Tezer $130.00 Santoni - Urban Santoni Urban $635.00 NEW! Mezlan - Dabour Mezlan Dabour $275.00 NEW! Jeffery-West - Grave Chukka Jeffery-West Grave Chukka $336.00
Jeffery-West - Dirk Jeffery-West Dirk $588.00 Marc New York by Andrew Marc - Hillcrest Mid Marc New York by Andrew Marc Hillcrest Mid $228.00 Original Penguin - Birdie Original Penguin Birdie $180.00 Original Penguin - Birdie Original Penguin Birdie $180.00
Trask - Brady Trask Brady $265.00 Armani Jeans - Leather Chukka Boot with Contrast Sole Armani Jeans Leather Chukka Boot with Contrast Sole $305.00 Vivienne Westwood - Boot Brogue Vivienne Westwood Boot Brogue $435.00 H by Hudson - Houghton H by Hudson Houghton $160.00
H by Hudson - Houghton H by Hudson Houghton $160.00 Ralph Lauren Collection - Polo Refined Prestwick Ralph Lauren Collection Polo Refined Prestwick $550.00 Mezlan - Grassi Mezlan Grassi $355.00 NEW!
Zappos Family Core Value:

10. Be Humble