N
ew York City, the late 1950s — free jazz emerges as the new soundtrack of the youth, a generation defined by angst and subversion who esteem indulgence as the high road to liberation. Charlie Parker is king, and the confines of convention are crumbling along with the puritan ideals that defined it. Beatniks wander the village, shedding their Ivy League blazers for casual leisurewear, and the women take cues from abroad, namely Italy and France — the length of skirts shrank and skin become an accessory to flaunt. So sets the tone of Anthony Minghella’s film The Talented Mr. Ripley, based on the Patricia Highsmith novel of the same name.

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Dickie Greenleaf is a young, affluent Princeton grad from New York City who’s living (lavishly) off his father’s trust fund checks in the sunny pastures of Mongibello, Italy. A young man named Tom Ripley, mistaken by the senior Greenleaf as a colleague of his son’s, is persuaded to go fetch Dickie and bring him home. Unbeknownst by everyone he meets, however, is that this Tom Ripley character may have an agenda of his own, his talents hidden in “forging signatures, telling lies and impersonating almost anyone”.

The tensions of this slow-burning psychological thriller are borrowed from film noir, but anchored in the sunny, idyllic backdrop of southern Italy in the ’50s. When the film premiered in 1999, it received glowing reviews from critics. Roger Ebert gave it four stars, his highest mark of excellence, while The New York Times called it “a scenic, voluptuously beautiful film”.

Nominated for five Academy Awards, including best costume design, the film is still remembered as a template for summertime style: the effortless marriage of Italian linen, cotton and Sperry-Topsider CVOs. Though we wouldn’t recommend gleaning general life lessons from Ripley and co. (instead, try our Guide to Life), the gang knew how to dress the part. Below are a few key moments from the film, and a handful of modern pieces to help you achieve the same timeless look.

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