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Cool & Classic Chukkas

There comes a time in every guy’s life when it’s time to swap those beloved sneakers for something a bit more stylized. Fret not. These chukkas are just as comfortable as your dependable kicks, yet they give the jeans and T-shirt formula a much-needed injection of sophistication. Pair any of these styles with cuffed chinos and a flannel button-down for a foolproof look this season. The details: Brands include John Varvatos, Timberland, Ben Sherman and more.




Timberland Boot Company Men's Eastern Standard Chukka





Timberland Boot Company Men's Eastern Standard Chukka

Durable and rustic workboot-inspired silhouette, burnished leather and suede, treaded sole...
Tretorn Men's Krona Mid Leather Chukka Sneaker





Tretorn Men's Krona Mid Leather Chukka Sneaker

Casual design with a napped upper, textured back panel, lace-up closure, non-slip sole Material:...
Kenneth Cole REACTION Men's Face Facts Chukka Boot





Kenneth Cole REACTION Men's Face Facts Chukka Boot

The fact is this low-cut ankle boot is an instant favorite in unlined burnished leather with a...

Ted Baker Men's Tullik 4 Chukka





Ted Baker Men's Tullik 4 Chukka

Versatile low-cut ankle boot in rich suede with a plain toe and highlighted by contrast stitching...
Ted Baker Men's Tullik 4 Chukka





Ted Baker Men's Tullik 4 Chukka

Versatile low-cut ankle boot in rich suede with a plain toe and highlighted by contrast stitching...
Ted Baker Men's Tullik 4 Chukka





Ted Baker Men's Tullik 4 Chukka

Versatile low-cut ankle boot in rich suede with a plain toe and highlighted by contrast stitching...

Patagonia Men's Advocate Chukka





Patagonia Men's Advocate Chukka

Keep warm while camping or lounging around in this lightweight design, flexible upper with...
Patagonia Men's Advocate Chukka





Patagonia Men's Advocate Chukka

Keep warm while camping or lounging around in this lightweight design, flexible upper with...
Eastland Men's Seneca Limited Edition Ankle Boot





Eastland Men's Seneca Limited Edition Ankle Boot

A classic design that gains character with time; lightly cushioned insole Material: leather...





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