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Marilyn Monroe in 'The Misfits,' 1961

Marilyn Monroe demonstrated the appeal of jeans in some of her earliest photo shoots, later filling out a perfect pair of Levi's in the Western drama "The Misfits." Decades after her death, Tommy Hilfiger purchased three pairs of her jeans at auction for $42,550, gifting one of the high-waisted, curvy pairs to sex symbol Britney Spears.

(CREDIT: Courtesy MGM)
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