You can’t beat a handsome checkered shirt, and this cotton version toes a stylish line between smart and effortlessly cool. Cut for a slim fit with a structured, tall spread collar it works just as well with lightweight chinos or a pair of classic denims. The buttoned patch pockets at front add that hint of cool to this shirt. Leave the top button undone and roll up the cuffs for a weekend look. Did you know: The shirt was an item of men’s underwear until the twentieth century.

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