Grace Kelly (1955, wearing Edith Head)
Looking icy-cool and “gorgeous, of course,” she collected her Best Actress award for The Country Girl and wed Prince Rainier of Monaco a year later. Designer “Edith Head understood the economics of how to design a dress.”
Barbra Streisand (1969, wearing Arnold Scaasi)
Mod about you: Streisand opted for a sparkling pants suit when she tied for Best Actress for Funny Girl. “She was a bohemian kid in 1969, so she stepped out in a way that made sense for her.”
Lauren Hutton (1975, wearing Halston)
The model-turned-actress showed up to present in a relaxed colorful gown with a fur jacket. “If you remove the fur, it looks pretty ho-hum.”
Diane Keaton (1978, wearing Ruth Morley)
The queen of chic menswear and Annie Hall victor “looked like she was going shopping on a Sunday afternoon and someone asked her, ‘Oh, do you want this Oscar?’”
Meryl Streep (1983, wearing Christian Leigh)
Good as gold: Meryl Streep picked up her second trophy (for Sophie’s Choice) while pregnant with daughter Mamie and still “couldn’t be any more glamorous.”
Cher (1988, wearing Bob Mackie)
Two years after donning a feathered headdress at the Oscars, the Moonstruck winner snapped out of it in a sheer Mackie original that, says Gunn, “is a great look for her because the proportions are good and she has a fantastic figure.”
Madonna (1991, wearing Bob Mackie)
Leave it to Madonna to perform a nominated song from Dick Tracy, hold date MichaelJackson’s hand and show up in “a Hollywood costume shop version of Marilyn Monroe” in one eventful night.
Sharon Stone (1998, wearing Vera Wang)
She paired her then-husband’s white button-down shirt with a floor-length couture satin skirt. The result? “A look that’s polished, elegant and a bit of a surprise.”
Celine Dion (1999, wearing John Galliano)
Near, far, wherever you are…Celine Dion’s backward white suit will go on as “a case of someone who was trying way too hard to be different.”
Gwyneth Paltrow (1999, wearing Ralph Lauren)
The night that she won her Oscar for Shakespeare in Love, Paltrow also inspired hundreds of “pretty in pink” puns. But Gunn says, “the dress is ‘fine’ in all lower-case letters. I like the color, but it’s bottom-heavy.”
Halle Berry (2002, wearing Elie Saab)
Berry made history as the first African American to ever land a Best Actress award—and she did it a “stunning” gown. “All these years later, it still looks modern.”
Jennifer Lopez (2003, wearing Valentino)
Jennifer Lopez, who presented that night, made a modest pistachio-colored gown look marvelous. “I love fashion risk-takers, and she took one and really looks beautiful,” says Gunn.
Helen Mirren, (2007, wearing Elie Saab)
The night that Helen Mirren ruled for The Queen, she stood out looking “breathtaking and exuding all the glamour of a young starlet!”
Lupita Nyong’o (2014, wearing Prada)
“She makes a magnificent presence in that gown and looks like a dream,” Gunn says of the 12 Years a Slave actress, who described her dress color as “Nairobi blue” in honor of where she grew up in Kenya.
Charlize Theron (2016, wearing Dior)
Charlize Theron’s red gown—complete with “a plunging neckline down to her belly button”—left a mark on the red carpet. And that borrowed 48.8-carat Harry Winston necklace “draws the eye right to her cleavage!” Next, Take a Look at 70+ Years of the Oscars’ Best Fashions
