I own a pair of gray chukka boots. I’m surprised just how much I wear them. The great thing about gray boots is that they ...

If you buy from a link, we may earn a commission. Learn more The casual look most often associated with chukka boots has sensible origins, even if they are a little muddled. The truth is that the ...

If you buy something via one of our links, we may earn a commission. The Clarks Eastridge Chukka Boots are just $57 right now at DSW when you use the code LASTCALL at checkout, bringing the ...

First seen back in April, we now bring you another look at this Wolf Grey/Black-White Lunar Flyknit Chukka. Already available in a countless amount of color schemes, this Flyknit Chukka utilizes a ...

The Swoosh continues to dish out woven options, as here we see an upcoming colorway of the Free Woven Chukka. The suede and leather pair sports a Cool Grey upper, which has been complemented with ...

Dr. Martens has boots available for a shocking price of just $85. Originally priced at $140, you’ll save $55 on the Dr. Martens Crewson Chukka Dapple Buck Casual Boots in Brown. Available for ...

The four-pronged collection allows two Vans Vault silhouettes in the Chukka Boot LX and Sk8-Hi LX to soak up the limelight, each rendition being finely tuned with colorful upper constructions.