The Awardist Oscars A history of Oscar fashion Take a look back at the most memorable red carpet moments from Hollywood's biggest awards show By Mary Sollosi Mary Sollosi Mary Sollosi is the former assistant features editor at Entertainment Weekly. She left EW in 2022. EW's editorial guidelines Updated on February 22, 2019 06:25PM EST Close 01 of 65 Oscar style through the years Bettmann Archive/Getty Images; Frazer Harrison/Getty Images (2); TIMOTHY A. CLARY/AFP/Getty Images; Michael Ochs Archives/Getty Images (2); Kevin Winter/Getty Images; Kevin Mazur/WireImage; John Barr/Liaison; Vinnie Zuffante/Getty Images; Michael Montfort/Michael Ochs Archives/Getty Images As the Oscar ceremony fast approaches, we're taking a stroll down memory lane — which, it turns out, is carpeted in red. As well as being markers of Hollywood history, every Academy Awards ceremony is a fashion time capsule. Here are 64 of the most essential red-carpet style moments from Oscars past. 02 of 65 Janet Gaynor (1929) Bettmann Archive/Getty Images Janet Gaynor was '20s-cool in a sweater and scarf when she accepted the first-ever Academy Award for Best Actress in 1929, for her performances in the films 7th Heaven, Street Angel, and Sunrise: A Song of Two Humans. 03 of 65 Mary Pickford (1930) FPG/Getty Images Mary Pickford was elegant in this beaded silk chiffon gown at the second Academy Awards, where she won Best Actress for her performance in Coquette. 04 of 65 Norma Shearer (1930) John Kobal Foundation/Getty Images Six-time nominee Norma Shearer accepted the third Oscar for Best Actress (for The Divorcee) in a shimmering floor-length dress with a matching fur-trimmed jacket. 05 of 65 Clark Gable (1935) Imagno/Getty Images Frankly, my dear, Clark Gable looked the part of the perfect movie star in 1935, when It Happened One Night swept the four main categories, including a Best Actor win for Gable. 06 of 65 Bette Davis (1939) SNAP/REX/Shutterstock Best Actress winner Bette Davis (for Jezebel) stopped the show in this dramatic full-skirted tulle gown, her face framed by egret feathers sewn along the neckline. 07 of 65 Vivien Leigh (1940) Bettmann Archive/Getty Images Vivien Leigh accepted the award for Best Actress in 1940 (for Gone with the Wind) wearing this floral Irene dress with a full skirt, the print and silhouette of which were atypical of eveningwear at the time. 08 of 65 Hattie McDaniel (1940) Bettmann Archive/Getty Images Hattie McDaniel was elegant in a turquoise dress and matching beaded jacket, with white gardenias at her collar and in her hair, when she made history as the first black artist to win an Academy Award. The venue where the 12th ceremony was held, the Cocoanut Grove at the Ambassador Hotel, made an exception to its racially discriminatory policy by allowing McDaniel to attend, but the Best Supporting Actress winner was still forced to sit at a separate table against the wall rather than with her Gone with the Wind costars. 09 of 65 Joan Fontaine (1942) Bettmann Archive/Getty Images In 1942, when the country was at war, female attendees were asked to tone down their evening wear; Best Actress winner Joan Fontaine (for Suspicion), pictured here with Ginger Rogers, wore a long-sleeved black dress with a matching black lace mantilla. 10 of 65 Jimmy Stewart (1942) Peter Stackpole/Life Magazine/The LIFE Picture Collection/Getty Images For 1942's somewhat more solemn wartime ceremony, Brigadier General Jimmy Stewart appeared in his Air Force uniform. 11 of 65 Olivia de Havilland (1947) Archive Photos/Getty Images The 1947 winner for Best Actress, To Each His Own star Olivia de Havilland, wore a pale-blue organza gown with a colorful string of flowers hand-painted across the bodice and down the full skirt. 12 of 65 Loretta Young (1948) AP/REX/Shutterstock Loretta Young was resplendent in abundantly ruffled emerald-green silk taffeta, accessorized with matching opera-length gloves, when she won Best Actress in 1948 for her performance in The Farmer's Daughter. 13 of 65 Marilyn Monroe (1951) 20th Century Fox/Kobal/REX/Shutterstock Marilyn Monroe made her only Oscar appearance at the 1951 show, when she presented in this dramatic black tulle gown. 14 of 65 Donna Reed (1954) Earl Leaf/Michael Ochs Archives/Getty Images Donna Reed embodied pure '50s glamour in this fitted strapless gown when she accepted the trophy for Best Supporting Actress (for From Here to Eternity) in 1954. 15 of 65 Audrey Hepburn (1954) NBC/NBCU Photo Bank via Getty Images Audrey Hepburn won her only competitive Oscar on her first nomination (of five), for Roman Holiday in 1954. The icon of chic accepted the honor in this belted boatnecked floral dress by her friend Hubert de Givenchy, who dressed her regularly. 16 of 65 Grace Kelly (1955) Bettmann Archive/Getty Images Legendary costumer Edith Head made Grace Kelly's ice-blue strappy silk sheath dress in 1955, when she was named Best Actress for her performance in The Country Girl. 17 of 65 Marlon Brando (1955) Michael Ochs Archives/Getty Images Marlon Brando looked sharp in a black tux when he accepted the award for Best Actor, for his performance in On the Waterfront, in 1955. 18 of 65 Miyoshi Umeki (1958) Earl Leaf/Michael Ochs Archives/Getty Images The only Asian actress to ever win an Academy Award, 1958's Best Supporting Actress (for Sayonara) Miyoshi Umeki wore a beautiful black kimono to the ceremony. Almost 20 years later, she destroyed her statuette. 19 of 65 Janet Leigh (1960) Hulton Archive/Getty Images Janet Leigh (pictured with then-husband Tony Curtis) rang in the '60s in this glittering belted sheath dress with white elbow-length gloves. 20 of 65 Rita Moreno (1962) Bettmann Archive/Getty Images When she won Best Supporting Actress for West Side Story in 1962, Rita Moreno wore a shimmery gown with a black bodice atop a full floral skirt. Over 50 years later, Moreno wore the dress again to the 2018 Oscars. 21 of 65 Sophia Loren (1963) Keystone-France/Gamma-Rapho via Getty Images Sophia Loren presented at the 1963 ceremony wearing a midi-length tulle dress with a voluminous textured collar. 22 of 65 Sidney Poitier (1964) Michael Ochs Archives/Getty Images For his historic 1964 Oscar win, when Sidney Poitier became the first black man to win Best Actor (for Lilies of the Field), he looked sharp in a white bow tie worn with a black morning coat. 23 of 65 Barbra Streisand (1969) ABC Photo Archives/ABC via Getty Images One of 1969's two Best Actresses (an honor she won for Funny Girl, tying with The Lion in Winter's Katharine Hepburn), Barbra Streisand delivered an Oscar look for the ages with these sequined, sheer Arnold Scaasi pajamas, finished off with a crisp white collar on top and huge billowing bellbottoms at her feet. 24 of 65 Diahann Carroll (1969) ABC Photo Archives/ABC via Getty Images In a pale pink gown with a sheer, glittering white overlay, Diahann Carroll brought ethereal glamour to the Oscar stage when she presented at the 1969 ceremony. 25 of 65 Diana Ross (1973) Bettmann Archive/Getty Images For her turn as a presenter at the 1973 show, Diana Ross went with menswear-gone-glam, choosing this silvery silk tuxedo by Bob Mackie. 26 of 65 Ann-Margret (1974) Michael Montfort/Michael Ochs Archives/Getty Images Ann-Margret experimented with fashion at the 1974 awards, wearing this rhinestone-covered cap atop a high-necked, skintight, beaded black sheath. 27 of 65 Lauren Hutton (1975) Michael Montfort/Michael Ochs Archives/Getty Images Presenter Lauren Hutton emanated breezy glamour at the 1975 show, where she wore a multi-pastel Halston gown accessorized with effortless loose hair and a luxurious fur coat. 28 of 65 Elizabeth Taylor (1976) Ron Galella/WireImage You could practically trace the history of Oscar style using the fashion of Elizabeth Taylor alone. One of the icon's most essential Academy Awards moments came in 1976, when she wore this strapless Halston dress — the color of which the designer then named "Elizabeth Taylor Red." 29 of 65 Jack Nicholson (1976) Michael Montfort/Michael Ochs Archives/Getty Images Jack Nicholson could not have looked more '70s cool when he accepted the Oscar for Best Actor in 1976 (for his performance in One Flew Over the Cuckoo's Nest), accessorizing his tuxedo with aviator sunglasses. 30 of 65 Diane Keaton (1978) Ron Galella/WireImage Annie Hall's iconic style lasted well after the credits rolled, with Diane Keaton bringing the character's signature look to the Oscar stage when she accepted the award for Best Actress for her performance in the film. 31 of 65 Farrah Fawcett (1978) Ron Galella/WireImage Farrah Fawcett didn't need a speck of jewelry to bring sparkle to her 1978 look, a glittery, drapey gold minidress. 32 of 65 John Travolta (1978) Ron Galella/WireImage A flowy-haired John Travolta lent his classic black tux some distinction in 1978, updating the look with a white silk scarf draped around his neck. 33 of 65 Raquel Welch (1979) ABC Photo Archives/ABC via Getty Images Presenter Raquel Welch didn't go for a gown in 1979, but rather a skintight, bright-blue sequined catsuit, accessorized with a wide gold choker at her neck. 34 of 65 Sigourney Weaver (1981) Ron Galella/WireImage Sigourney Weaver presented at the 1981 show, where she wore this shoulder-padded, elaborately draped white jumpsuit with flat shoes. 35 of 65 Jane Seymour (1981) Ron Galella/WireImage Presenter Jane Seymour glittered at the 1981 ceremony in this bright red dress dripping in silver fringe, her huge '80s hair cascading over one shoulder. 36 of 65 Jessica Lange (1983) Ron Galella/WireImage Jessica Lange went pure '80s when she won Best Supporting Actress (for Tootsie) in 1983, opting for this ice-blue, knee-length Valentino with long sleeves, shoulder pads, and rhinestones all over. 37 of 65 Anjelica Huston (1986) Ron Galella/WireImage We're green with envy over the vivid emerald Tzetzi Ganev gown Anjelica Huston wore to the 1986 awards, where she was named Best Supporting Actress for her performance in Prizzi's Honor. 38 of 65 Cher (1988) John Barr/Liaison How to choose just one Cher look? Every entry in the icon's collection of outrageous Bob Mackie Oscar ensembles is worthy of recognition, but we have to give the gold to what she wore when she won Best Actress in 1988 (for Moonstruck). The sheer beaded gown, accessorized with a matching wrap and earrings that drop down to her collarbone, was a genuine showstopper. 39 of 65 Spike Lee (1990) Ron Galella, Ltd./WireImage Best Original Screenplay nominee (for Do the Right Thing) Spike Lee dressed up his 1990 Oscar look with a brilliantly colored Kente cloth scarf. 40 of 65 Cindy Crawford (1991) Ron Galella/WireImage Cindy Crawford embodied early '90s glamour in this plunging red Versace, worn with natural makeup and voluminous blown-out hair, at the 1991 Oscars. 41 of 65 Michael Jackson (1991) David Mcgough/DMI/The LIFE Picture Collection/Getty Images Michael Jackson may have attended the 1991 awards with Madonna, but even the Material Girl (dressed like Marilyn Monroe) couldn't upstage Jackson's Oscar fashion game. The King of Pop defended his crown in a bedazzled white jacket, a huge diamond brooch, a thick black armband, and black gloves — yes, on both hands! 42 of 65 Marisa Tomei (1993) Barry King/Liaison When Marisa Tomei won Best Supporting Actress (for My Cousin Vinny) in a memorable upset, she accepted the trophy in this white silk organza Chanel with black piping, white lace insets, and a thick black bow at the waist. 43 of 65 Whoopi Goldberg (1994) Reed Saxon/AP Photo For her 1994 hosting gig, Whoopi Goldberg took the stage in this long-sleeved, empire-waisted gown in luxe brown velvet. 44 of 65 Oprah Winfrey (1995) Jeff Kravitz/FilmMagic When she presented the Jean Hersholt Humanitarian Award to Quincy Jones in 1995, Oprah wore this long-sleeved, collared brown dress with a black tulle train. 45 of 65 Susan Sarandon (1996) Barry King/Liaison Susan Sarandon's bronze Dolce & Gabbana halter gown, which she wore whe she won Best Actress for Dead Man Walking in 1996, is now housed at the Met, and is the only Oscars dress in the museum's collection thus far. 46 of 65 Nicole Kidman (1997) Kevin Mazur/WireImage Nicole Kidman never fails to own the Oscars carpet whenever she attends, but the one look that made waves above all the Aussie's others was the daring chartreuse chinoiserie sheath she wore to the 1997 ceremony (with then-husband Tom Cruise). The embroidered, fur-trimmed Dior gown was a fashion risk for the actress — Joan Rivers hated it — and a red carpet game-changer. 47 of 65 Cate Blanchett (1999) Steve Granitz/WireImage Cate Blanchett has been a consistent Oscars style star ever since her very first Academy Awards as a nominee (for Best Actress for Elizabeth) in 1999. The actress hit the carpet in this slinky John Galliano creation, the sheer back embroidered with flowers and hummingbirds. 48 of 65 Gwyneth Paltrow (1999) TIMOTHY A. CLARY/AFP/Getty Images Gwyneth Paltrow brought pink back when she won Best Actress (for Shakespeare in Love) in 1999 wearing this sweet Ralph Lauren dress. She finished off the girlish look with a Grace Kelly-esque chignon and a diamond choker, bracelet, and earrings. 49 of 65 Uma Thurman (1999) Kevin Mazur/WireImage To perform presenting duties at the 1999 ceremony, Uma Thurman chose this platinum Chanel halter and full skirt, accessorizing the glamorous two-piece look with glittering sandals and a bejeweled armband. 50 of 65 Julia Roberts (2001) Kevin Winter/Getty Images Julia Roberts accepted the Oscar for Best Actress (for her performance in Erin Brockovich) in 2001 wearing this vintage Valentino gown with white straps and a black tulle train. 51 of 65 Björk (2001) Vinnie Zuffante/Getty Images Who could possibly forget Björk's swan dress? Created by designer Marjan Pejoski, the garment has gone down in Oscar history as one of the most iconic red-carpet looks of all time. 52 of 65 Renée Zellweger (2001) Chris Weeks/Getty Images Presenter Renée Zellweger shone at the 2001 awards in this canary-yellow column dress, a vintage Jean Dessès gown from the 1950s. 53 of 65 Jennifer Lopez (2001) Kevin Winter/Getty Images Attending the 2001 ceremony as a presenter, Jennifer Lopez shocked some critics with this Grecian-inspired Chanel, the sheer top half of which left little to the imagination. 54 of 65 Halle Berry (2002) TIMOTHY A. CLARY/AFP/Getty Images On the night she became the first (and thus far only) black woman to ever win the Oscar for Best Actress (for Monster's Ball), Halle Berry delivered both a moving acceptance speech and a legendary fashion moment. She accepted her award in this deep-red Elie Saab gown with a strategically embroidered mesh bodice atop a full taffeta skirt. 55 of 65 Hilary Swank (2005) Jeff Kravitz/FilmMagic Hilary Swank accepted her second Oscar for Best Actress (for Million Dollar Baby) and made a fashion splash in this backless navy Guy Laroche dress in 2005. 56 of 65 Salma Hayek (2005) Carlo Allegri/Getty Images For the 2005 awards, presenter Salma Hayek wore this fitted navy Prada gown with black sequined embroidery and ribbon detail. 57 of 65 Michelle Williams (2006) Frazer Harrison/Getty Images Best Supporting Actress nominee Michelle Williams (for Brokeback Mountain) stole the show on the 2006 Oscars' red carpet in this marigold silk-chiffon gown by Vera Wang. 58 of 65 Helen Mirren (2007) Lester Cohen/WireImage Helen Mirren won Best Actress for The Queen in 2007 and looked nothing less than regal when she did it, wearing this champagne gold Christian Lacroix with a gilded skirt and beaded lace bodice. 59 of 65 Freida Pinto (2009) Kevin Mazur/WireImage Slumdog Millionaire won big at the 2009 Academy Awards, where its star Freida Pinto served as a presenter and served up a stunning red carpet look with this one-sleeved sequined cobalt gown by John Galliano. 60 of 65 Angelina Jolie (2012) Ethan Miller/Getty Images Angelina Jolie looked wonderful in this black Atelier Versace gown when she presented at the 2012 Oscars, but it was her right leg — which she never moved from its position sticking out of the skirt's high slit — that made headlines and inspired a meme. 61 of 65 Jennifer Lawrence (2013) Jason Merritt/Getty Images Everyone remembers when Jennifer Lawrence tripped on her way to the stage to accept the Oscar for Best Actress (for Silver Linings Playbook) at the 2013 ceremony — but just as memorable is the strapless white Dior dress in which she did it. 62 of 65 Lupita Nyong'o (2014) Jeffrey Mayer/WireImage Lupita Nyong'o made every best-dressed list in 2014, when she won the Oscar for Best Supporting Actress (for 12 Years a Slave) wearing this pale-blue Prada gown with a sparkling headband. 63 of 65 Kate Hudson (2014) Jason Merritt/Getty Images Presenter Kate Hudson brought Old Hollywood glamour to the 2014 awards with this caped, plunging white Versace. 64 of 65 Mahershala Ali (2017) Frazer Harrison/Getty Images Winning Best Supporting Actor for Moonlight in 2017, Mahershala Ali became the first Muslim actor to win an Academy Award — and he dressed for the occasion with this monochrome Ermenegildo Zegna Couture tux. 65 of 65 Janelle Monáe (2017) Frazer Harrison/Getty Images Janelle Monáe appeared in two of 2017's Best Picture nominees (Hidden Figures and winner Moonlight), and she represented them both stylishly at the ceremony in this spectacular black tulle Elie Saab Haute Couture gown with a sheer embroidered bodice over a full, elaborately embellished skirt.