Celine Dion

Over the course of her decades-long career, Celine Dion has worn a lot of outfits that landed her in multiple best-dressed lists, but she certainly made a fashion statement when she appeared at the 1999 Academy Awards wearing a reversed white suit from Dior. She stepped up to the plate looking like the ultimate girl boss with a solid credit score, single-handedly serving a bold high-fashion look at one of the biggest nights in Hollywood.

It was a ballsy move for the songstress to wear a white Christian Dior tuxedo backward and with a matching white fedora and diamond-studded Ray-Bans at that. As bizarre as it may seem, the look made a strong and lasting impression and remains to this day as one of the most memorable looks at the Oscars.