"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."
—Kim France, editor in chief
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."
—Caroline Kinneberg, assistant online editor
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."
—Meredith Kahn Rollins, executive editor
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."
—Noria Morales, market editor
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."
—Julia Topolski, accessories director
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."
—Emily McCarthy, editorial assistant
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!"
—Jen Ford, fashion news director
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."
—Hope Greenberg, fashion director
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."
—Jackie Nasser, fashion editor
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."
—Kendall Herbst, fashion news editor
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."
—Lynette Pone, senior market editor
Farrah Fawcett, 1978
"Just effortlessly sexy—like she walked off the beach, slipped into this liquidy-gold dress, and went out."
—Laurel Pinson, online editor
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."
—Melissa Lum, accessories editor
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."
—Christina Perez, assistant online fashion editor
"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!"
—Elise Loehnen, editor-at-large
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."
—Alexandra Willinger, associate fashion editor
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 looks...cool."
—Cristina Mueller, senior beauty editor
Nicole Kidman in Jean Paul Gaultier, 2003
"I'm crazy about the Grecian draping on this dress: The idea is so simple yet elegant."
—Anne Kwon Keane, market director
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."
—Suzanne Singer, associate accessories editor
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."
—Kathryn Irby, fashion features associate
Emily Blunt in Calvin Klein, 2007
"The sequins in an inky blue shade add just enough sparkle without overpowering the look."
—Jenny Kang, associate market editor
Tatum O'Neal, 1974
"She looked so chic and sophisticated for a 10-year-old."
—Andrea Linett, creative director
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."
—Rebecca Malinsky, market assistant
Elisabeth Shue, 1996
"She has the best-ever glow plus the best-ever hair!"