There’s a video on YouTube of Gianni Agnelli being interviewed in 1988, striking the sartorial balance of tradition and modernity for which he was renowned. Perched on a Le Corbusier love seat, L’Avvocato—as the law student turned businessman was known—is clad in an impeccable yet sedate suit, looking every bit the Italian industrialist. His sole quirk: a pair of driving shoes that were relatively casual—pebbled driving moccasins by now-defunct shoemaker Giulio Miserocchi. The image—and its subject’s mix of an off-duty shoe with full corporate garb—depicts a combo that feels as fresh today as it did then. That’s in part because it stands in direct contrast to the shambolic “old-money aesthetic,” with its strict, nonsensical rules about how to look rich, that the world has had to endure for the past several seasons. But it also serves as a reminder that real style is as individual as the person in the clothes...