The usually forward-thinking songstress's Galliano pantsuit topped trousers with a reversed tuxedo jacket. Dion accessorized with a fedora and $25,000 diamond-studded specs.
Barbra Streisand 1969
The Funny Girl winner's bell-bottomed Scaasi ensemble looked like sheer madness, but in fact it was strategically lined with flesh-tone fabric.
Kim Basinger 1990
In a single-sleeve dress of her own design, Basinger "looked like Glinda the Good Witch after six or seven scotches," reported L.A.'s now-defunct Herald Examiner.
Designer Bob Mackie said he spun this web of minimalist glitz after Cher requested an outfit that would "let them see that everything still looks good." "Some of those outfits for Cher will follow me to my grave," he admitted to Women's Wear Daily.
Geena Davis 1992
Costume designers Bill Hargate and Ruth Meyers helped the Thelma & Louise nominee with the long and short of Oscar dressing.
Dolly Parton 1990
Hello, Dolly! The never-shy singer got plenty of attention in a low-cut turquoise sparkler by designer Tony Chase.
Demi Moore 1989
Moore, who presented the cinematography award, designed her own bustier, bustle and bicycle-shorts ensemble, which W dubbed "A Fright to Remember."