Diego della valle was born into a family of cobblers in a small town in Le Marche, just off Italy’s Adriatic coast. At the tender age of 16, he came up with the concept for a comfortable, beautifully made loafer to wear on weekends. The Gommino driving shoe transformed his life and the lives of those around him. 

During our visit to Diego’s hometown of Casette d’Ete, it became clear just how much of a hero the Tod’s founder is to all the locals. From the chef who whipped us up an unbelievable eight-course meal in a restaurant overlooking the sea to the pretty young child-minders at the Tod’s crèche, everyone broke into a smile when Diego’s name was mentioned. “He cares about the quality of his products, but he also cares about the quality of our lives—and that’s rare,” said one of the seamstresses. “I am so proud to work for him.”

We photographed Diego in his offices in Milan. Housed in a beautiful mansion just a short walk from the Duomo, the city’s famous cathedral, the wooden floors and high ceilings made an ideal setting for the shoot. Diego was a natural in front of the camera, chatting easily with the photographer and paging through Italian Touch, a coffee-table book he commissioned on the chicest men in Italy, to work out how to stand for the camera.

Despite being a huge fan of Hong Kong style and culture, Diego insisted on the photo shoot taking place in Italy. “I would love to be shot in Hong Kong; it would be such fun with all those skyscrapers. The energy there would make anything fun, to be honest—it’s infectious,” Diego said with a laugh. “But I’m very proud to be Italian, and our company is built on the concept of ‘Made in Italy’ and the unique quality that comes from this wonderful country. So I think the images need to show me in Italy, be it Milan or Capri or Rome. And luckily for us, Italy is rather photogenic, so it’s not too much of a hardship.”

Turn to page 128 in the August 2015 issue of Hong Kong Tatler for the full story

Photography by Leonardo Rinaldesi