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Cate Blanchett in John Galliano, 1999

"This John Galliano dress—with flowers and a hummingbird embroidered on a very sheer, very low-cut panel down the back—was just so utterly unexpected, so out of the box and so daring that I couldn't take my eyes off it. It still seems to me like one of the greatest evening dresses ever."
Grace Kelly in Helen Rose, 1956

"A timeless dress, pulled-back hair, and simple white gloves—Grace Kelly makes looking like a princess so effortless."
Julia Roberts in vintage Valentino, 2001

"When she walked out in this dress, I remember thinking: Oh, wow. It's simple but not plain, monochromatic but not boring. The white details at the front, the stripy train ... it all comes together beautifully."
Anjelica Huston, 1975

"I love how her super-sleek look manages to be totally '70s ... but perfect for a classy show like the Oscars. It's also super-sexy without being very revealing."
Michelle Williams in Vera Wang, 2006

"First there's the color of this dress, and then there's that beautiful silhouette. And her makeup—clean face and a red lip—completely complements the look. It's a bold choice played out perfectly."
Reese Witherspoon in vintage Christian Dior, 2006

"It doesn't get much more stunning than Dior from the '50s. The dress fits perfectly, and the beadwork is dazzling. It stands out without being distracting or overbearing."
Lauren Hutton, 1980

"I love when someone goes against the dress code and winds up looking better than anyone at the party: Hutton in 1980—shorts and a sweatshirt were never more glamorous!"
Julianne Moore in YSL, 2003

"I love that Moore bucked the accepted wisdom that redheads shouldn't wear green. The combination of the hair, the incredible emerald drop earrings, and the jade dress was amazing."
Audrey Hepburn in Givenchy, 1954

"She epitomizes 1950s ladylike glamour, from her pixie haircut to her lacy Givenchy full skirt and her simple pearl drop earrings."
Gwyneth Paltrow in Calvin Klein, 1996

"She looks like she just slipped on the dress, added a bit of red lipstick, grabbed Brad, and was ready to go. I love the minimal ease of it all."
Cameron Diaz in Emanuel Ungaro, 2002

"There's nothing I don't like about Cameron in this long floral wrap dress. She had an effortless boho vibe."
Farrah Fawcett, 1978

"Just effortlessly sexy—like she walked off the beach, slipped into this liquidy-gold dress, and went out."
Chloë Sevigny in YSL, 2000

"I love how at first glance, she invokes Hollywood nostalgia in her sleek, plunging YSL halter, but you could so easily envision her off to an indulgent night at Studio 54."
Norma Shearer, 1930

"There's something so ethereal about Shearer in this brocade dress with the matching fur-trimmed jacket—and the armful of bracelets and pinned corsage of flowers are just the right touch of glamour."
Björk, 2001

"She's not exactly a traditional sort of person, so why would she try to do red carpet in a traditional way? So she wore a swan dress and people still talk about it today. You just have got to admire it!"
Elizabeth Taylor in Halston, 1976

"For me, the Oscars represent the epitome of glamour, and this striking red dress was as quintessentially glamorous as it gets—so appropriately worn by Elizabeth Taylor."
Diane Keaton, 1978

"Let's take an inventory of what she's wearing: a full skirt, a scarf, and a men's jacket—and what you can't see in this shot are the high-heeled sandals, lace tights, and harem pants. She is wearing this TO THE OSCARS. And yet despite the inherent craziness of the outfit, she actually"
Nicole Kidman in Jean Paul Gaultier, 2003

"I'm crazy about the Grecian draping on this dress: The idea is so simple yet elegant."
Natalie Wood, 1962

"While I don't wear fur myself, I love how chic Natalie Wood's looks over a halter gown all in the same color. Plus, the jeweled bracelets worn over her gloves are the ultimate in Old Hollywood glitz."
Janet Leigh, 1960

"My all-time favorite look is when Janet Leigh appeared at the 1960 Oscars in a slim fitted dress dripping in sequins, with a mandarin collar, a high-waisted belt, and opera gloves to boot! It's sleek and completely unstuffy."
Emily Blunt in Calvin Klein, 2007

"The sequins in an inky blue shade add just enough sparkle without overpowering the look."
Tatum O'Neal, 1974

"She looked so chic and sophisticated for a 10-year-old."
Maggie Gyllenhaal in Prada, 2005

"Gyllenhaal's Prada gown at the 77th Academy Awards is perfect. It's a combination of glitzy old-fashioned glamour and modern embellishment. She did a great job of keeping it timeless and current all at once."
Elisabeth Shue, 1996

"She has the best-ever glow plus the best-ever hair!"