Gianni Agnelli once took Jackie and Caroline Kennedy sailing off the Amalfi coast. When they got back, Jackie had a telegram from her husband waiting for her: “More Caroline,” it said, “Less Agnelli.”

Agnelli could make even presidents jealous. As the head of the Italian car company Fiat, he was one of the most visible industrialists in the world – and he was by far the most stylish. He mastered the art of sprezzatura – the Italian mode of making meticulously planned outfits look like they’d been casually thrown together, sometimes pairing Caraceni suits with deerskin hiking boots, or a bespoke suit with a skewed tie knot.

He became famous for his quirky use of accessories – he wore his ties outside of his sweaters and his wristwatches over his shirt cuffs – but his style went far beyond its iconoclastic touches and influenced men’s fashion for generations. Esquire has called him one of the five most fashionable men of the last century. His grandson, Lapo Elkann, wears his old suits and has become something of a fashion figure in his own right. Upon his retirement, Nino Cerruti called Agnelli one of his biggest inspirations, next to James Bond and, fittingly, John F. Kennedy.