CHUKKA BOOTS ARE the ultimate easygoing, do-it-all footwear. From rugged work chukkas to desert boots inspired by the boots that British soldiers wore in WWII, they come in a variety of silhouettes ...

The Madson II boot is available in four colors; it’s a dressy chukka boot style that’s also waterproof for peace of mind on cloudy days. Typically $190, it’s discounted by as much as 45% ...

Sorel Men’s Carson Chukka Waterproof Boots: We loved the look, feel, and weight of these boots after working them in, but like the rigid leather, the competition was too stiff to put them above ...

Not all waterproof boots are chunky and heavy, and Allen Edmonds proves it, with this chukka boot's gorgeous brogue detail. Seeing as we're menswear experts, you know this is a style we love—you ...

Our seasoned Hoka wearer breaks down the popular running shoe brand’s lineup for tackling all kinds of trails.

Chukka boots are ankle-high leather boots ... suede can be worn year-round. Just make sure you waterproof suede chukkas before their first foray out “into the wild.” Reapply the waterproofing ...

Every woman needs a sleek Chelsea boot in her wardrobe, and this one from Sperry is both stylish and comfortable. The classic ...

For winter 2025, Adamiyatt is also loving Freda Salvador's reimagined take on the classic chukka featuring a ... chance against these durable, waterproof snow boots. Don't believe us?