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Kick Off Fall With These Eight Updated Chukka Boots

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Welcome to Guys Buys, our new weekly segment dedicated to our male readers and the ladies who shop for them. Each week, our Menswear Specialist Mickey Sery will bring a roundup of seasonal products for men—whether you need some style assistance or just like to shop.


Cole Haan Air Colton Winter Chukka in in Black Iris, $228

Recently the chukka boot has emerged as a staple in men's shoe options. The history of the minimal ankle boot stems from the traditional game of polo. During World War II, the chukka boot was fitted with a crepe sole and renamed the desert boot.

It's easy to find these boots in the usual brown suede or leather, but if you want to make more of statement this fall, try a patterned or mixed-material option. We've done the footwork for you by rounding up eight styles to help you update your boot style without falling flat.


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Cole Haan

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