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25. 1968: Julie Andrews
In 1968, Julie Andrews showed up to the red carpet in a black cocktail dress that was perfectly on trend for the '60s. It featured a high turtleneck neckline, billowing sheer sleeves, and a full taffeta skirt. The bodice was made with black velvet, and she accented her neck with a diamond broach in the center.

At that time, Andrews had a certain good-girl image in the public consciousness, thanks to her smash hits like Mary Poppins and Sound of Music. "Millions rush to see her pictures because the public sees in Julie Andrews the idealized female. Pure, good, sweet, virtuous, amusing, intelligent, and altogether adorable," wrote Independentin 1968. "That, at least, is what they think she is."

But that was all about to change, and her dress could have been hinting at that re-branding. That year, Andrews was in the middle of starring in two brand-new pictures that would change her image. The first was Star!, the biography of Gertrude Lawrence, and Darling Lilli, a World War I comedy where she appeared in a shower scene and did a strip tease. This dress was the perfect embodiment of that transition — it was sweet and girly with its frills and poufs, but also mature and just a little gothic and edgy.