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Top 100 Plain Woman movies

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If the Shoe Fits (1990)

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A modern Cinderella in Paris: While the plain Kelly Carter works as a dresser for the famous fashion designer Francesco, she dreams of designing shoes for him. However she can't win his attention... until she helps a good fairy on the street who, unbeknownst to Kelly, enchants a pair of Kelly's shoes so that she turns into a supermodel whenever she wears them. She attends Francesco's Ball and immediately wins his heart. Now, how can she make him love her real self?