Audrey Hepburn goes from princess to tourist in this simple, yet stunning ensemble in Roman Holiday. A smart white button-down blouse, a striped scarf, a belted flowing skirt and espadrilles (maybe a nod toward the gladiators who used to roam the very same streets?) make this the perfect outfit to vacation in. It allows the wearer to breathe, while walking on cobblestone and visiting landmarks, without sacrificing style. (Fun Fact: Our editors have been to Rome a collective eight times between them, and both have admitted to emulating this look each time they visited the Italian city.) Costume designer Edith Head won an Oscar for her wise choices in this film, and would eventually collect eight Academy Awards in her lifetime. Obviously, she was on to something if the look still inspires over 55 years later… So “when in Rome,” dress like Audrey.