From Cher’s towering custom headdress in 1986 to Reese Witherspoon’s vintage Dior gown in 2006, the most glamorous looks to grace the Oscars red carpet required weeks of pin-pricking labor, said Bronwyn Cosgrave, author of Made For Each Other: Fashion and the Academy Awards, and host of the fashion podcast A Different Tweed. As for each look’s finishing touches, “we usually spend about two hours in hair and makeup,” said celebrity makeup artist Molly R. Stern. Keep reading to learn how much time and effort went into putting together 15 of the most legendary Oscars looks. 
Julia Roberts The week of the 2001 Oscars, every designer was vying for Julia Roberts to wear one of their creations. Former supermodel Cristina Viera, who worked at the Valentino boutique on Rodeo Drive in Beverly Hills, tried on this black-and-white column gown and called it “the kind of dress in which she could really look like an Old Hollywood movie star,” she told Cosgrave. Cristina practiced walking up and down stairs in the dress. Once she was sure Julia could move to and from the stage, she sent it to the actress’s stylist, Debbi Mason. The morning of the Oscars Cristina got a call—it was Debbi, saying Julia would wear the dress. Julia won Best Actress for her role in Erin Brockovich that night. 
Farrah Fawcett As a presenter at the 1978 Oscars, Farrah Fawcett wore a gold chainmail top and skirt by Stephen Burrows. Whiting & Davis, a company that specializes in metal gowns and handbags, reached out to the legendary designer to make the set. “[Farrah] came to my showroom at Bendel’s because she saw it in the press,” Stephen told Better You. “After I sent the pattern, it took a week to make the chainmail. It fit her perfectly.” 
Reese Witherspoon Reese Witherspoon took home the 2006 Best Actress award for her role in Walk the Line in a romantic vintage 1955 Christian Dior gown, according to her stylist, Leslie Fremar. Because Leslie bought the dress already made at Didier Ludot, a vintage shop in Paris, it required relatively little time to tweak, said Cosgrave. “At the most, it was just tailored.” Reese’s makeup artist, Molly R. Stern, told Better You, “Enhancing Reese’s natural beauty wasn’t hard—we got her done in about an hour and spent the rest of the time clinking glasses.” 
Cher In 1986, Cher caused a major stir in her custom-made Bob Mackie ensemble. “This piece is probably one of the most laborious outfits ever created for the Oscars,” Cosgrave said. “Cher started plotting it as soon as she received her invitation to present the Best Supporting Actor trophy” about a month before the show. When the singer attended a rehearsal the week of the event, she found out that to get onstage, she’d have to walk under an arch. So she had the arch measured to ensure her punky headdress would fit beneath it. But she didn’t account for the limo ride—her headpiece was so tall she had to crouch on the floor of the car on her way to the Oscars, Cosgrave said. 
Lupita Nyong’o Cosgrave called the 2014 Best Supporting Actress winner’s Prada look the culmination of a relationship Lupita shared with the brand for over a year. “Lupita’s stylist, Micaela Erlanger, started creating a red carpet identity for Lupita for the 12 Years a Slave premiere in October 2013, where she wore a Prada dress. Her Oscars dress in 2014 was in a shade called ‘Nairobi blue’ to honor her Kenyan heritage.” Lupita’s makeup artist Nick Barose used waterproof and long-lasting Chanel formulas because “between the potential for crying and the rain, I wanted to make sure the look would last.” 
Halle Berry Cosgrave said that as soon as nominations came out in early February 2002—back when the Oscars aired in late March—Halle Berry’s stylist Phillip Bloch “hit the ground running” in his quest for the perfect dress. He pulled this hand-embroidered Elie Saab gown straight from the Fall/Winter 2001 Couture runway. “That kind of embroidery on couture is very labor-intensive,” Cosgrave said. The time spent crafting the dress was well worth it because that night, Halle became the first black woman to win a Best Actress award for her role in Monster’s Ball. 
Audrey Hepburn Cosgrave said the white lace dress Audrey Hepburn wore when she accepted the 1954 Best Actress award for Roman Holiday has been wrongfully attributed to Hubert de Givenchy, who dressed the star for many years. But it was Edith Head, the costume designer for Roman Holiday, who custom-made this dress for Audrey. It took several weeks in her atelier at Paramount Pictures. 
Chadwick Boseman In 2019, Chadwick Boseman attended the Academy Awards alongside his Black Panther co-stars in custom Givenchy Haute Couture, paired with David Yurman jewelry, according to Cosgrave. The jacket was hand-beaded, so the look took several weeks to complete. “Think fittings for the suit, days of workmanship on the embroidery; all in a Paris atelier, plus jet time getting the suit to L.A.,” Cosgrave said. 
Janelle Monáe Janelle Monáe’s stylist, Maeve Reilly, told WWD that when she first saw this embroidered gown in the Elie Saab Fall 2016 Couture collection, she knew it was the one for the actress’s 2017 Oscars appearance. “We [were deciding] back in December if this was going to be our dress,” Maeve said. “It was a moment where we saw her in it, and I cried. I’d never seen anything so beautiful in my life.” Similar to the other looks on this list, Janelle’s makeup took about an hour, “with 20 minutes focused on perfecting her brows,” makeup artist Jessica P. Smalls said. “I also spent a lot of time prepping her skin. I added some bronzer into her moisturizer for the glow.” 
Björk As iconic as Björk’s swan dress is, Cosgrave said there wasn’t much planning behind it. Macedonian designer Marjan Pejoski told Vogue he didn’t even know the singer wore his dress to the 2001 Oscars until the following morning. “She borrowed a lot of Pejoski’s pieces throughout the promotion of the film Dancer in the Dark and then put this one on the day of the Oscars,” Cosgrave said. The finishing touch? An egg, designed by Björk’s then-partner Matthew Barney, which she dropped from her dress and “laid” on the red carpet. 
Elizabeth Taylor At the 1961 Oscars, Elizabeth Taylor was named Best Actress for her role in Butterfield 8 while wearing this chiffon and embroidered faille evening gown from Marc Bohan’s Dior Haute Couture Spring-Summer collection of the same year. Each season, the Dior team sent Elizabeth sketches of designs so she could see them several weeks before she hit the red carpet, according to Cosgrave. “She never went to fashion shows,” Cosgrave said. “She would just look at something she liked and buy it.” 
Barbra Streisand Arnold Scaasi dressed Barbra Streisand in 1969 when she tied with Katharine Hepburn for Best Actress for her role in Funny Girl. “This was a custom piece that Arnold spent several weeks making,” Cosgrave said. “Unfortunately, he made it out of sheer chiffon, which was completely transparent.” Stylists today spend weeks planning their clients’ Oscars looks around the cameras so that wardrobe malfunctions like this don’t happen. “Though we had taken every aspect of the sequin outfit into consideration, we did not know that the flashbulbs used by the press would wipe out the flat surface of the black net,” Arnold said. “Next morning Barbra was on the phone with me, laughing about the whole episode.” 
Nicole Kidman Nicole Kidman’s embroidered chartreuse gown came from John Galliano’s first Dior Couture collection, Cosgrave said. “It was a spontaneous choice,” made when the collection debuted about two months before the 1997 Oscars, according to the September 2001 issue of Harper’s Bazaar. Another Dior client purchased the dress, but it didn’t deter Nicole’s styling team from going after it. “By couture protocol, they had to ask the client if it was OK if Nicole Kidman wore that dress to the Oscars,” Cosgrave said. That client had been skiing in Aspen at the time, but the team got the OK. The second they did, Dior tailors made two trips from Paris to London to fit the dress on Nicole. 
Spike Lee When Spike Lee’s film BlacKkKlansman won for Best Adapted Screenplay in 2019, the director stood out from a sea of black tuxes in his custom Ozwald Boateng suit. Per designer Philippe-Olivier Amany, a custom Ozwald Boateng creation takes eight weeks to make and requires three fittings. Ozwald is in London, so when Spike attended the BAFTAs there two weeks before the Oscars, he likely went in for a fitting, said Cosgrave. Then the suit made its way from the U.K. to L.A.. 
Zoe Saldana “This was a dress that came from Riccardo Tisci’s Givenchy Haute Couture Spring 2010 show, so it went straight off the runway, onto her,” Cosgrave said of Zoe Saldana’s dreamy 2010 Oscars look. The collection debuted in late January, a little over a month before the Oscars. Zoe’s makeup artist Vera Steimberg told the L.A. Times she used all Nars products. “We wanted to give her the sexy, sophisticated look, but fresh,” Vera said. “I concentrated more on her eyes and her skin, keeping colors neutral for the lips and cheeks.”
How Long It Really Took to Create 15 Iconic Oscars Looks
This is how the teams behind these mesmerizing Oscars outfits made it all happen.
