Looking forward to Sunday’s 86th Academy Awards, InStyle‘s Editor-at-Large Hal Rubenstein dishes to Time.com on some of the Oscar dresses that turned heads and blazed new trails in fashion in years past. Every year at the Oscars, actresses walk the red carpet looking to make a forever positive impression, but only a small number of gowns have had a lasting impact on both Hollywood and fashion history. From Grace Kelly‘s splendorous silk gown designed by Edith Head that she wore in 1995 to Jennifer Lawrence‘s body-hugging, red Calvin Klein dress from 2011, the Oscars have produced some of the world’s most famous and jaw-dropping gowns of all time.

However fascinated we are with Oscar dressing, Rubenstein says they could use a bit more flair. “What are the Oscars missing these days? Cher! It’s really that simple,” Rubenstein says. “We long for a woman who has that sense of flamboyance, the humor, the wit, the in-your-face drama that Cher just embodies.” Her Bob Mackie designed ensemble that she wore to the 1996 Oscars stole the show, and she made her mark on history. “The red carpet is really about familiar glamour. The glamour that we’re used to, the glamour we were brought up with from the movies,” states Rubenstein. When actresses do something odd or different, viewers are shocked, as was the case with Cher and Tilda Swinton‘s asymmetrical Lanvin gown from 2008 that threw everyone for a loop.

Dresses that walk the red carpet can have a major impact on the success of a design house, but Rubenstein suggests that we forget how much the right dress can shape the career of an actress. “We overlook the impact a dress might have on a little known actress who is wearing a fantastic gown,” Rubenstein says. For example, at the 79th Academy Awards, Keira Knightley strode out in a burgundy taffeta Vera Wang ball gown, and the then little-known actress became a sensation by the next morning, and her career took a huge leap forward. From shocking looks to haute couture creations, check out all of Rubenstein’s thoughts on revolutionary Oscar fashion in the video above!

Then, tune in to the Oscars this Sunday, March 2nd on ABC at 7PM EST/4PM PST, and stay set to InStyle.com as the night goes on for all the up-to-the-moment red carpet updates.

Want more Oscar dresses? See what the best actress winners of the past 20 years wore in our gallery.