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GINGER ROGERS & MIRANDA COSGROVE: 20
It's hard to believe Fred Astaire's future dance partner was just out her teens when she posed for this 1931 portrait in highly styled hair and sophisticated makeup. iCarly's Cosgrove, meanwhile, sports a looser look that's less ballroom and more bust a move.
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CLARA BOW & SHAILENE WOODLEY: 21
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JOAN COLLINS & EMMA ROBERTS: 22
Thanks to her jet-black hair, striking eyes and bold red lip, Collins became known throughout the '50s as "the poor man's Elizabeth Taylor," landing sultry roles in films like 1955's The Girl in the Red Velvet Swing. At the same point in life, We're the Millers star Roberts is keeping her look more low-key, but she can still rock a photo op.
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DEBBIE REYNOLDS & EMMA WATSON: 23
By 1955, Reynolds had tap danced alongside Gene Kelly in Singin' in the Rain and been named America's sweetheart, courtesy of her girl-next-door good looks – or make that woman next door; those curled bangs certainly add a few years! Watson, meanwhile, hardly looks a day out of Hogwarts, despite graduating to edgier roles. "The allure of being sexy never really held any excitement for me. I've never been in a terrible rush to be seen as a woman," The Bling Ring star told W magazine.
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KATHARINE HEPBURN & EMMA STONE: 24
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DORIS DAY & RIHANNA: 25
Two blondes, two (very) different beauties. Sweet-as-pie Day became one of the top stars of all time thanks to sly sex comedies like 1959's Pillow Talk, and she maintained her signature wholesome style throughout her career. "Bad Girl" RiRi, on the other hand, changes her look with each new song, but she's also setting her own records, with the most No. 1 hits in Billboard history. Still, can she top Day's catchy "Que Sera, Sera"?
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OLIVIA DE HAVILLAND & HILARY DUFF: 26
A natural beauty, de Havilland often played plain women, including Gone with the Wind's Melanie Hamilton. "I have always had more luck with good girl roles because they require more from an actress," the star – still going strong at 97 – has said. Like de Havilland, Duff can easily switch from demure to dazzling, whether for a new role or the red carpet.
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LENA HORNE & EMILY VANCAMP: 27
From nightclub singer to Hollywood star, Horne exuded elegance with her perfectly coiffed hair, flawless makeup and glamorous gowns. VanCamp revs up her look for Revenge, but would prefer to keep things casual and cosmetics free. "When I take off my makeup, that's my boyfriend's favorite," she told Women's Health magazine.
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AVA GARDNER & ANNA KENDRICK: 28
Irresistible as ever in 1950, green-eyed Gardner had her choice of roles – not to mention men: One year after posing for this portrait, she married her third husband, Frank Sinatra. Perhaps Kendrick is starting to take tips from Gardner's screen-siren playbook: She recently showed off her sexy side by posing in a bra for GQ.
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DONNA REED & KATHARINE MCPHEE: 29
Four years after 1946's It's a Wonderful Life, wholesome head-turner Reed became a popular pinup and went on to star in a string of hit movies and her own TV series, The Donna Reed Show. McPhee is a Smash in her own right, winning admirers with her sexy-sweet looks and golden pipes.
See more timeless beauties in our Gorgeous at Any Age special, on newsstands Sept. 6!