The 10 Most Iconic Oscars Beauty Looks of All Time

There are nights in Hollywood that feel less like events and more like mythology in motion. The Academy Awards is one of them—and this year’s Oscars will take place on Sunday, March 15, when cinema’s finest gathers in L.A. to honor the performances of the year. On the red carpet, hair and makeup looks are not incidental: they are intentional, orchestrated, and immortalized in a single frame.

Since the first Academy Awards ceremony was held in 1929, there have been key celebrity beauty moments that have transcended trend and entered a historical canon. These are the looks that altered the aesthetic conversation, emboldened generations of makeup artists, and defined what we now recognize as timeless glamour. Below, we talked to 10 celebrity makeup artists, hair gurus, and skin experts about their favorite beauty moments from the Oscars—the looks that still make a statement and are inspiring a whole new crop of beauty enthusiasts today.

Barbra Streisand, 1969

“This is one of many looks that were and continue to be simultaneously inspiring and iconic. The beauty is a masterclass in restraint and precision,” says Carolina Gonzalez, whose client list includes Sabrina Carpenter and Gigi Hadid. “The eye carries the entire story: a perfectly sculpted cut crease that lifts the lid with clean, graphic intention while making the eyes appear larger and more open. The liner is delicate, almost whispered, and the lashes stay soft so the architecture of the crease can breathe. The skin is luminous and nearly bare, allowing the eye to remain the focus. The long, center-parted hair creates a contrast to the deliberate geometry of the makeup. This was a perfect moment where mod artistry met Streisand’s unmistakable presence, creating one of the most memorable beauty statements ever, in my opinion.”

Elizabeth Taylor, 1970

“It has to be Elizabeth Taylor at the 1970 Academy Awards,” declares Sandy Linter, an icon in the beauty industry herself (Linter worked with Jackie Kennedy, Lauren Hutton, and Debbie Harry, among many others). “She was unforgettable with her deep, natural tan, jewels in her cleavage, and raven hair piled up high. The makeup emphasized her violet eyes with black liner and jet-black mascara. Her natural beauty showed through the makeup. Elizabeth’s skin is gleaming and polished, glowing like her diamonds. She wore a gorgeous lavender gown by legendary costume designer Edith Head, and matched her shadow perfectly to the dress. Dramatic Grecian curls complemented the look. That image of her may be dated, but it has stayed with me forever as being the look for the Oscars.”

Cher, 1977

“Ahead of her time and entirely singular, Cher’s beauty and style were always unmistakably her own. Each appearance felt almost thematic; an extension of her persona as much as her fashion,” says Genevieve Herr, who has worked on faces like Eva Mendes, Amanda Seyfried, and Julia Roberts. “The luminous shimmer across her cheekbones revealed a woman who understood her features intimately and knew exactly how to accentuate them. Her glossy lip caught the light beautifully—but it was the extraordinary lashes that transformed this look into something truly unforgettable. Long before dramatic lashes became commonplace, Cher wore them with fearless conviction. They gave the entire look a sense of theatrical glam, and long pink nails added an extra note of playful drama. It was a look built on confidence as much as artistry. Cher had the rare ability to walk into a room wearing anything and make it entirely her own.”

Lauren Hutton, 1975

“I love Lauren Hutton at Oscars circa 1975,” says Romy Soleimani, whose clientele includes Tracee Ellis Ross, Greta Lee, and Julianne Moore. “Beyond her striking features, Lauren’s beauty has always radiated from within, illuminating everything on the outside. Bronzed but soft, the makeup is strong and subtle, not overworked—just elegant and timeless and it feels easy, very much like Lauren: modern then and modern now.”

Rihanna, 2023

“Never one to play by the rules, Rihanna has long treated fashion as her playground; the mogul’s second pregnancy did nothing to slow that fearless approach,” UZO, the makeup artist and cofounder of UZO Beauty, says. (She should know about fearlessness—she works often with fashion vanguards like Wunmi Mosaku.) “At the 2023 Academy Awards, where Rihanna was nominated for Best Original Song for Lift Me Up from Black Panther: Wakanda Forever, she delivered a red-carpet moment that was a master class in modern maternity dressing—not concealed, but celebrated. What made the Alaïa gown truly sing was the balance between fashion and beauty. While the silhouette leaned bold and directional, her makeup anchored the look in classic beauty. A softly sculpted complexion, matte red lip, and warm, bronzed tones echoed the chocolate hues of the outfit, creating a rich monochromatic harmony. And her sleek top knot kept the focus on her face.”

Michelle Williams, 2006

“One of my all-time favorite Oscars looks is Michelle Williams at the 2006 Academy Awards in that unforgettable, canary-yellow Vera Wang gown,” says Mélanie Inglessis, a favorite of Jenna Ortega and and Ruth Negga for glam. “The color alone was such a bold and inspired choice. I also loved her lipstick, which I found to be beautifully chosen: a vibrant orange-red that complemented the yellow so harmoniously without overpowering it. The balance of tones felt intentional and refined.”

Cher, 1988

“It’s impossible to talk about Oscar looks without mentioning Cher,” says Robin Black, who is both a photographer and a makeup expert. “In 1968, she made her debut in a futuristic metallic pink gown with a Cleopatra-inspired eye, followed by the yellow beaded Bob Mackie in 1973 with lashes for days, the dreamy lavender-floral-fairy moment in 1974, a series of glittering gowns paired with dramatic eye makeup looks in 1983 and 1984, and the legendary feathered headdress in 1986. But the beauty look that has always stayed with me is 1988, the year Cher won Best Actress for Moonstruck. Amid all the glitzy Bob Mackie drama and sparkling ornamentation, the focus is entirely on her face. It’s refined, elegant makeup at its very best, perfectly complementing Cher’s striking bone structure. Her eyes were sculpted with cool matte shadows and smudged black kohl at the lash line. Her cheekbones were defined with warm bronze—no blush or shimmer, just structure. The brows were polished but natural, and the look was finished with a brownish nude lip. And in a moment I’ve always appreciated, Cher thanked her longtime makeup artist, Leonard Engelman, in her acceptance speech. For anyone interested in the history of makeup artistry in Hollywood, he is a name very much worth knowing.”

Halle Berry, 2002

“Honestly, Halle Berry’s glam is so good because she never tries too hard, says Patrick Ta, founder of Patrick Ta Beauty and Gigi Hadid’s makeup go-to.“She always looks like she’s been kissed by the sun, but in the most natural way. For her 2002 Oscars look, her skin is glowy and sculpted, and the warm bronze tones tie in perfectly with her Elie Saab dress. I love that the lip is soft and looks like her natural lip color, but just a kiss better. Everything is fresh and effortless. In my opinion, this Oscars look is iconic because this makeup look is timeless.”

Grace Kelly, 1955

“Before there was Gwyneth, Charlize or Nicole, there was Grace Kelly. Her 1955 Best Actress win for The Country Girl remains, to me, the epitome of classic Hollywood glamour,” says Molly R. Stern, makeup artist to stars like Maya Rudolph and Natasha Lyonne. “The mint-green satin gown she wore was made from $4,000 worth of French silk, which was a staggering fortune at the time. Her beauty look was the perfect complement: impeccably balanced, with hair that was swept into a polished updo with fresh yellow roses. Her makeup enhanced rather than competed—softly defined eyes with precise liner and mascara; pale, luminous cheeks; and a bold coral-pink lip that became the focal point of the look. It has inspired me for years, and continues to define what true red-carpet elegance means.”

Gwyneth Paltrow, 1999

“Gwyneth Paltrow’s look at the 71st Academy Awards remains one of the most iconic examples of understated red-carpet beauty,” adds celebrity makeup artist Sarah Uslan, who works with Dakota Johnson and Olivia Colman. “Her Ralph Lauren gown, paired with the angelic makeup artistry of Kevin Aucoin, defined soft, feminine elegance. Her skin was luminous and fresh, embodying an effortless glow with sheer coverage. I loved seeing her freckles shine through, and the rosy, balmy flush on her cheeks. Her lip color captures that natural ’90s tone we all try to emulate today, while the soft highlight on the inner corners of her eyes and along the brow bone opens and brightens the gaze, adding a dreamy element. Nothing felt heavy or overly sculpted and it was simply about enhancing her natural features. Even today, the look feels incredibly relevant.”