8. Grace Kelly, 1958
In 1958, Kelly wore a playful dress to the Imperial Ball at the Astor Hotel, where she and her husband were the guest of honor. Her dress had a show-stealing organza bow in the front, which was topped off with a bouquet of flowers at the knot. The royal styled her hair with chic curls that highlighted her stunning features. This dress perfectly shows off the Oscar-winner's elegant yet daring fashion choices. The oversized bow complements the minimal fabric and silhouette.