As the host of the Academy Awards in 1993, Whoopi Goldberg wore a purple bolero jacket lined with a shiny lime green fabric with a long train that showed off her shining pants underneath. Weird? Yes. Memorable? Definitely. (Photo: Getty Images)
Halle Berry’s Elie Saab gown, featuring a sheer top with floral appliqué and an attached iridescent skirt, will forever be remembered. (Photo: Getty Images)
Before stylists ruled the red carpet world, Demi Moore attended the Academy Awards in 1989 and wore a black-tie gym outfit. (Photo: Getty Images)
Julia Roberts dressed like a winner for the 2001 Academy Awards in a black-and-white Valentino number. (Photo: Getty Images)
Bette Middler’s Beauty and the Beast-inspired gold gown was accompanied by colorful tulle sleeves and poofy hair. (Photo: Getty Images)
Gwyneth Paltrow had an ultimate princess moment, wearing Ralph Lauren at the Academy Awards in 1999, when she won the award for best actress for her role in Shakespear in Love. (Photo: Getty Images)
Always one to get people talking, Anna Nicole Smith did just that with her teal velvet gown at the Oscars in 1996. (Photo: Getty Images)
Hillary Swank’s Guy Laroche gown reminded designers everywhere to never forget about the back. (Photo: Getty Images)
Susan Sarandon seemed to be going for rocker princess with her gold gown and round-frame sunglasses. (Photo: Getty Images)
At the height of Bennifer (Ben Affleck + Jennifer Lopez), the singer attended the 2003 Academy Awards wearing a mint green Valentino number. The couple didn’t last, but everyone will always remember the dress. (Photo: Getty Images)
Faith Hill sang “Somewhere over the Rainbow” at the Academy Awards in 2002 — and wore a dress to match. (Photo: Getty Images)
Lupita Nyong’o’s light-blue dress from Prada will forever be etched in fashion people’s minds for her twirling ballerina moment at the 2014 Academy Awards. (Photo: Getty Images)
The Icelandic singer might not have been best dressed, but she gave the awards show one of its most iconic looks by showing up to the 73rd Annual Academy Awards wearing a swan as a dress. (Photo: Getty Images)
Angelina Jolie’s leg might be remembered more than her black Versace gown at the 84th Annual Academy Awards, in 2012. (Photo: Getty Images)
Lizzy Gardiner’s dress was made out of 254 American Express cards. Hey, at least they were gold. (Photo: Getty Images)
Jennifer Lawrence’s fall might go down in Oscars history as one of the best moments, but her Dior Haute Couture gown surely will be remembered too. (Photo: Getty Images)
Jodie Foster bought the blue ruffle dress that she wore to the Oscars in 1989 off the rack. (Photo: Getty Images)
Charlize Theron might’ve been at the 2004 Oscars for her role in Monster, but she looked anything but that in a gorgeous Gucci gown. (Photo: Getty Images)
Celine Dion at least got points for trying something totally crazy and unique when she wore a backwards white tuxedo to the Oscars in 1999. (Photo: Getty Images)
Goldie Hawn was the pinnacle of cool — and still is, to this day — when she stepped out in a light-blue Versace number during the 71st Annual Academy Awards. (Photo: Getty Images)
Margot Kidder’s gown was a better fit on the set of Little House on the Prairie as opposed to the Oscars red carpet. (Photo: Getty Images)
Who could ever forget Michelle Williams’s bright yellow Vera Wang dress and Fred Leighton necklace at the Academy Awards in 2006? Her date was pretty exceptional too. (Photo: Getty Images)
Geena Davis seemed to take her fashion inspiration from a Madonna music video for the 1992 Oscars. (Photo: Getty Images)
Sometimes more is better. Case in point: Penelope Cruz’s voluminous Atelier Versace gown featuring a feather skirt and emboridered bustier at the Academy Awards in 2007. (Photo: Getty Images)
Tilda Swinton’s known for her daring fashion choices. But at the 2008 Oscars, the ill-fitting black gown she chose was certainly not one of them. (Photo: Getty Images)
Cindy Crawford might’ve been Richard Gere’s date to the 1993 Oscars, but her curve-hugging Herve Leger gown made her the center of attention. (Photo: Getty Images)
Uma Thurman called her Christian Lacroix dress at the 2004 Oscars one of her “most embarrassing experiences.” (Photo: Getty Images)
Juliette Lewis’s look mixed ’90s cultural influences (cornrows and Brad Pitt) with some from the past (a flapper-inspired gown and long pearls) for the Academy Awards in 1992. (Photo: Getty Images)
Even best-dressed stars fall sometimes. Charlize Theron’s Dior Couture gown was a beautiful color, but the wrinkly material and odd chest accoutrements made it a total fail. (Photo: Getty Images)
Cher called on her go-to guy Bob Mackie to make her a naked dress (before naked dresses were even a thing) for the 1988 Academy Awards. (Photo: Getty Images)
