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15 Most Iconic Red Carpet Dresses of All Time (2 of 3)

Cher: 58th Academy Awards in 1985

People are still talking about the brave ensemble Cher wore at this show. Critics told her that she was not awarded an Oscar for her role in Mask because she didn’t dress seriously enough to be taken seriously. So she doubled down and showed up on the red carpet in a jaw-dropping Bob Mackie showgirl costume.

Sharon Stone: 70th Academy Awards in 1998

This classic look from Sharon Stone is quintessential of 90’s fashion. She wore a combination of Gap and Vera Wang at this show, and looked absolutely stunning and classy.

Gwyneth Paltrow: 71st Academy Awards in 1999

Gwyneth Paltrow’s pink Ralph Lauren dress for the Oscar is still discussed today, as either a beautiful gown or a big disaster.

Halle Berry: 74th Academy Awards in 2002

Halle Berry took a risk with a scanty but stunning embroidered Elie Saab dress at this awards show, with a beautiful vine design as the centerpiece — a look that has aged well over the years.

Hilary Swank: 77th Academy Awards in 2005

Hilary Swank showed off her back in a super low cut Guy Laroche gown on this red carpet, showing off her muscular build from recent training for “Million Dollar Baby.”