Tutto sotto controllo”—everything’s under control—Diego Della Valle observed contentedly, to no one in particular, on a bright recent morning as he strolled into Rome’s Colosseum, which was empty except for a photography crew busily preparing to take his portrait. Off-hours access inside Italy’s most famous monument is a nice perk that comes with pledging $34 million for its restoration, as Della Valle, president and C.E.O. of the Tod’s Group, one of Italy’s leading fashion brands, did in 2011.

In 2016, the Tod’s donation also allowed Della Valle to host, at the landmark, one of the most splendid dinners Rome has seen since the Caesars. To celebrate the completion of Phase One of the project—in which the building’s soot-covered travertine was painstakingly cleaned with purified water and returned to its original, creamy-pink hue—Della Valle invited 300 guests for dinner at candle-lit tables perched on the upper tier of the ancient amphitheater. Prime Minister Matteo Renzi sat with Della Valle.