The Talented Mr Ripley
The Talented Mr Ripley may have graced cinema screens on the cusp of the millennium turning in 1999, but its sun-soaked evocation of late-1950s style is the definitive template for the quietly elegant dress code of the travelling moneyed.
As Dickie Greenleaf, Jude Law was the American in Europe with the enviably endless wardrobe. The look is American prep meets Italian playboy. Button down polo shirts, crisp chinos, espadrilles and Cuban collar shirts (and impeccable ironing) combine to make one of the best-dressed figures in cinema history.