1998: Madonna

Madonna is a timeless figure and a well-known trendsetter when it comes to fashion. Whatever she wears, people tend to follow. Her style sense was proven true in 1998 when she attended the Oscars with her brother Christopher. During the occasion, she wore a blue gown with an open corset and a splash of baby blue tulle. In addition, she wore a gleaming diamond and sapphire necklace.

Despite often being flamboyant and stylish, Madonna was surprisingly reserved in her choice of outfit at the time. Regardless, she still managed to shine brightly among the many attendees of the awards show. The frock, in addition to the corset, showcased her physique and beauty. Thus, it is not surprising that it is among the best dresses to have ever appeared at the Academy Awards. In addition, the piece’s great acclaim can be given credit for launching the career of its designer, Olivier Theyskens.