Red Wing 9096 Caverly Chukka Boot

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—01. Black Esquire leather.

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I recently discovered Red Wing’s Caverly Chukka, a style which doesn't seem to be offered by many of the brand's stockists, and was duly impressed. The timeless two-eyelet boot fits my utilitarian requirements for everyday leather footwear, and would work seamlessly with any casual jeans and T-shirt uniform. Made in Minnesota on the Postman last with a Gro-Cord Medallion sole, I can only imagine how incredible they'd look after years of regular wear.

—Available from Red Wing Amsterdam