The Most Memorable Glam in Oscars History
From Cher’s pastel eyeshadow to Zendaya’s flowing waves.
As we count down to Sunday’s Oscars, our excitement is building — not only to see who takes home the trophy but to witness how each celebrity gets done up. The Academy Awards represent the pinnacle of cinematic recognition, with even a nomination securing a place in history for any actor. With all eyes on Hollywood, this night becomes a celebration of more than just film but also fashion and beauty, as stars are styled — and done up — by the very best in the industry. Whether it’s a chic accessory or an elegant chignon, these looks have become as unforgettable as the performances themselves.
To celebrate acting’s big night, we’re rounding up some of our favorite looks from the past 97 years of the Oscars. From Audrey Hepburn’s go-to winged liner to Cher’s purple eyeshadow, here is some of the most memorable glam in Academy Awards history.
Audrey Hepburn
A true Academy Awards show icon, Audrey Hepburn graced the event countless times throughout her life. Her timeless beauty, highlighted by her signature winged eyeliner and fringe, remains our absolute favorite.
Cher
What can we say about Cher? Words hardly do her justice. An Oscar darling, her fashion and makeup are always executed flawlessly, even to this day. Here, her sparkling purple eyeshadow complemented her breathtaking floral dress, making her look absolutely divine.
Winona Ryder
“Winona forever,” a phrase uttered so often in the ’90s that Johnny Depp got it tattooed on his arm. Ryder, a cherished actor known for her roles in Girl, Interrupted and Beetlejuice, rocked this beautiful finger-wave pixie cut during the 1994 awards show.
Charlize Theron
The year she won the Oscar for her transformative role in Monster, Charlize Theron captivated the world stage with her bleach blonde brows and sunset-hued eyeshadow — a look that, when paired with her Gucci dress (designed by Tom Ford), left a lasting impression.
Angelina Jolie
Yes, beauty historians might vote Angelina Jolie’s looks in later years as the best in Oscar history but for us, it was when she won “Best Supporting Actress” for Girl, Interrupted. Her long black hair and dark eyeliner gave goth all the way.
Halle Berry
We’d like to think that television watchers gasped in unison when Halle Berry stepped out on the red carpet in this sheer floral dress and her classic pixie cut, the year she won “Best Actress” for her unforgettable performance in Monster’s Ball.
Lupita N’yongo
A dove blue dress, a bejeweled headband and sparkling eyeshadow — this stunning look from Lupita Nyong’o is never leaving our minds.
Lady Gaga
Lady Gaga knows how to make a statement and her 2014 Oscars look was no exception. From her ruby red lip to her chignon bun with a bow, every detail was a masterclass in unforgettable glamour.
Zendaya
We all know and love Zendaya — she never misses with her red-carpet gowns and her glam. Her super-long, sleek waves took her 2021 Oscars appearance to the next level.
For more award show coverage, check out our round-up of the most memorable Golden Globes looks of all time.
