Meryl Streep
Having won three Oscars and been nominated for a dozen more, Meryl Streep was a star before she even began acting. She looked classic with her date at prom in a boat neck white dress and silky, white, gloved hands.
Brad Pitt
He was a total heartthrob in the 1990s and not much has changed since then. He has aged like a fine wine, keeping his boy-next-door good looks. In his teen days, he looked adorably dorky in a shimmery, silver suit.
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