When the red carpet rolls out for the Academy Awards, Hollywood’s biggest stars step out dressed in some of fashion’s most extravagant gowns and some even dare to take risks. Dating back to Barbra Streisand‘s Oscar moment in 1969, the nominated actress took home a golden statute for her role in Funny Girl clad in sequined Scaasi evening pajamas. “I didn’t realize the outfit was so see-through,” she told InStyle. “You couldn’t tell that in the dressing room.”
In the years following, starlets including Celine Dion and Halle Berry have followed in Streisand’s steps wearing looks that have kept everyone talking—like this backwards John Galliano for Christian Dior tuxedo and peek-a-boo embroidered Elie Saab gown—and for good reason. They made outrageous Oscar gowns a trend and we culled our favorite 24 looks from over the years just in time for the 86th annual Oscars ceremony.
Click through the gallery to see more daring looks and be sure to check back here this Sunday, March 2 beginning at 6:00 p.m. EST to see just who might take the “most outrageous” title at this year’s ceremony.