1Roman Holiday, 1953
Hellin KayBest Dressed: Audrey Hepburn (duh) as Princess Ann in ankle-length skirts and neckerchiefs.
2Three Coins in the Fountain, 1954
Hellin KayBest Dressed: Jean Peters and Dorothy McGuire as two secretaries who travel to Rome looking for love—in the most quintessential (and chic) 1950s garb.
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3La Dolce Vita, 1960
Hellin KayBest Dressed: Anita Ekberg—full stop—as Sylvia. That black strapless sweetheart neck dress? Come. On.
4The Roman Spring of Mrs. Stone, 1961
Hellin KayBest Dressed: Vivien Leigh as Karen Stone—because her outfits are as boss-lady as her character (she plays a woman who will not allow anyone to define her by her age).
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5L'Eclisse, 1962
Hellin KayBest Dressed: Monica Vitti as Vittoria—no one has ever looked so beautiful in a shift dress, or in bed.
6Light in the Piazza, 1962
Hellin KayBest Dressed: Yvette Mimieux as Clara Johnson because #weddingdressgoals.
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7Mamma Roma, 1962
Hellin KayBest Dressed: Anna Magnani as Mamma Roma. She masters fierce do-not-mess-with-me appeal in every single scene. While wearing running in a dress.
8Gidget Goes to Rome, 1963
Hellin KayBest Dressed: Cindy Carol as Gidget in that amazing pink tweed Jackie O-esque suit.
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9The Talented Mr. Ripley, 1999
Hellin KayBest Dressed: Gwyneth Paltrow as Marge Sherwood—no one does a Roman vacation wardrobe as well as Marge.
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