In men’s clothing, we get most of our traditions from England, but our best casualwear from the US and Italy. Take footwear, for example. Where the English have given us traditional oxfords, derbys, and brogues, it’s the Italians and Americans who have come up with the best slip-ons. In the US, there are boat shoes, tassel loafers, penny loafers, and various incarnations of the handsewn moccasin; in Italy, there are Gucci horsebit loafers and driving mocs. The number of Italian styles in this case is smaller than what the Americans have to offer, but their significance is no less important. It’s the Italian slip-on that you want if you need something on the dressier side of casual.
Gucci loafers are too flashy for my taste, but I really like drivers in the summer. They were most famously worn by Gianni Agnelli in the mid-century, which is perhaps why we associate them with that carefree lifestyle along the Amalfi coast and the Italian sense of sprezzatura. As the story goes, Agnelli started wearing them after his car accident in 1953. His then lover, Pamela Harriman, caught him with another woman, and while he was fleeing, he crashed his Ferrari into the back of a lorry. The accident left him with a bad foot, so he needed to wear soft, more comfortable shoes.