Let’s be honest: the real thrill of Oscars night isn’t always who takes home the gold—it’s who shows up on the red carpet and delivers a fashion moment we’ll be talking about for years. The Oscars carpet has become a stage of its own, where elegance meets daring, and sometimes even controversy. Over the decades, celebrities have turned this runway into a space for risk-taking, reinvention, and cultural statements. From classic gowns to jaw-dropping style risks, these are ten red carpet ensembles that didn’t merely catch our attention—they redefined Hollywood glamour.
10. Cameron Diaz in Ungaro Couture (2002)
Among a sea of ballgowns and sequins, Cameron Diaz took a decidedly different turn, and it paid off. At the 2002 Oscars, she glided down the carpet in a flowy Emanuel Ungaro Couture gown with a laid-back, bohemian twist. It wasn’t dripping with crystals or custom-fit, but that was the whole idea. Diaz demonstrated that personality and confidence can radiate more than trickery. This “relaxed glam” moment remains exemplary proof that comfort and fun can have a place on the red carpet, the largest in Hollywood.
9. Céline Dion’s Backwards Dior Tuxedo (1999)
Only Céline Dion could successfully rock one of the most daring and bizarre red carpet options ever. She showed up in 1999 in a backwards-worn crisp white Christian Dior tuxedo with a tilted fedora. It was brazen, it was baffling, and it instantly became iconic. Polarizing when it debuted, Dion’s ensemble has matured into a cult classic, revered for its bold experimentation with gender-bending style. It wasn’t about belonging—it was about being different, and that’s precisely why it’s unforgettable.
8. Lakeith Stanfield’s Saint Laurent Jumpsuit (2021)
When Lakeith Stanfield walked the carpet in 2021, it was as though it was a blast from the past to the 1970s—coolness factor included. His bespoke Saint Laurent jumpsuit by Anthony Vaccarello included dagger collars, billowy pant legs, and a cinched waist, epitomizing sheer disco attitude. What was even more striking was that the look had been adapted from a woman’s runway gown, dissolving the boundaries between male and female fashion. Stanfield’s appearance wasn’t merely fashionable—it was a look at what red carpet fashion might be like in the future: bold, fluid, and completely fearless.
7. Ariana DeBose’s Valentino Hybrid Look (2022)
Hot on the heels of her Oscar victory for West Side Story, Ariana DeBose demonstrated that the red carpet can be as revolutionary as the award itself. She appeared in a custom Valentino piece that mixed sharply tailored tuxedo pants with a sweeping, dramatic cape, all in a bold red color. The look was both potent and glamorous, an ideal reflection of DeBose’s message of authenticity and inclusivity. It was glamour that honored both strength and femininity—and it made her one of the night’s most buzzed-about celebrities.
6. Barbra Streisand’s Arnold Scaasi Jumpsuit (1969)
It was 1969, and Barbra Streisand didn’t simply accept her Oscar for Funny Girl—she set a red carpet precedent. Rather than a gown, she sported a shimmering, diaphanous Arnold Scaasi jumpsuit, featuring flared pants and a mischievous collar. When she wore it, the transparent fabric was a shock, but Streisand had such poise that the look became a style legend. Her daring selection paved the way for other stars to break the rules and demonstrated that bold risks might pay off in spectacular ways.
5. Lupita Nyong’o’s Prada Gown (2014)
Few Oscar gowns have become as iconically immediate as Lupita Nyong’o’s ethereal blue Prada gown. Drifting onto the carpet in 2014, the hue alone—called “Nairobi blue” after her city of origin—spoke volumes. With its lacy folds and billowy shape, the dress resembled something out of a contemporary fairy tale. And when Nyong’o subsequently grasped her Oscar for 12 Years a Slave, the dress was forever cemented in awards-season lore as an exercise in unadulterated elegance and representation.
4. Rihanna’s Alaïa Maternity Look (2023)
Rihanna has always defied the rules of fashion, and her 2023 Oscars look solidified that pregnancy only makes her style more fearless. Wearing a bespoke Alaïa jumpsuit with leather accents and a semi-sheer panel that accentuated her baby bump, she redefined maternity fashion on one of the globe’s most prominent stages. Rather than conceal, she flaunted—and the outcome was a bold testament to the fact that glamour exists in every shape. It was quintessentially Rihanna: unapologetic, fearless, and effortlessly cool.
3. Björk’s Swan Dress (2001)
Perhaps the most infamous Oscars outfit of all time, Björk’s swan dress was part performance, part fashion experiment, and completely unforgettable. Designed by Marjan Pejoski, the feathery piece literally wrapped around her neck, complete with an egg-shaped purse. Critics at the time didn’t know what to make of it, but that was the point. The appearance has since then been a pop culture icon, parodied from sketch comedy to Halloween party attire. Love it or loathe it, you can’t help but be impressed.
2. Halle Berry’s Elie Saab Gown (2002)
When Halle Berry hit the red carpet in her fleshed-out Elie Saab gown back in 2002, it was pure Hollywood magic. The gown’s elaborate embroidery and bold transparency made it one of the most stunning ensembles the Oscars had ever witnessed. But what really cemented its place as an icon was what occurred afterward: Berry became the first black woman to receive the Best Actress award. The dress and the groundbreaking moment became one, forging one of the most significant red carpet moments in history.
1. Hattie McDaniel’s Turquoise Gown (1940)
Three decades before the Oscars were a worldwide fashion extravaganza, Hattie McDaniel arrived at the ceremony in a turquoise dress that was as meaningful as it was fashionable. She won the first Academy Award given to a Black woman that evening, for her performance in Gone with the Wind. But McDaniel had to receive her award at a segregated table, an agony that made her appearance all the more poignant. Her dress was not just a fashion icon but also a testament to her strength, opening the door for future generations.
The red carpet at the Oscars has never been simply a procession of attractive gowns—it’s an art form of self-expression, a display of courage, and cultural revolution. By way of sophistication, rebellion, or simply stark peculiarity, these ensembles demonstrate that fashion can be as powerful as the movies they’re honoring. Ultimately, the path to Oscar glory is often prefaced by one moment of irrevocable style.