1999: Céline Dion

Céline Dion, back in 1999, was one of the most popular singers out there, with her song My Heart Will Go On becoming famous thanks to it being featured in the movie Titanic. When she attended the Oscars that year, she took an unconventional approach to how many dresses at the occasion. Instead of a dress, Dion opted for an all-white tuxedo. Not only that, she wore her tux backward and paired the whole affair with a white hat and black sunglasses. The outfit was designed by John Galliano.

When her outfit made the appearance, it quickly drew strong opinions from many due to how absurd it was. While the singer is no stranger to unconventional fashion tastes, her attire at the time certainly became the most talked-about out of all the dresses and suits that were worn. To her credit, Dion certainly owns her fashion choices.