Red carpets have long served as the runway for celebrities, showcasing their most glamorous looks and unique styles that etch their names in fashion history.
While it may be easy to achieve the title of "best dressed," creating an iconic look is a whole different challenge.
From glimmering gowns to avant-garde ensembles that push the boundaries of fashion, celebrities know how to play the fashion game in ways that leave a lasting impact.
With that in mind, take a look at the top 10 most iconic celebrity red carpet looks of all time.
1. Billy Porter – 2019 Oscars
Billy Porter made a powerful statement when he graced the red carpet at the 2019 Oscars in a stunning tuxedo gown designed by Christian Siriano.
While he wasn't the first man to wear a dress on the red carpet, fashion critic Robin Givhan noted that Porter's tuxedo gown marked the arrival of gender-blurring fashion in a bold and mainstream way.
By breaking traditional gender norms in an environment known for its rigid fashion codes, Porter aimed to spark conversations about masculinity and the acceptance of diverse identities in fashion.
2. Angelina Jolie – 2012 Oscars
Angelina Jolie proved she didn’t need to wear anything dramatic to stand out at the 2012 Oscars.
Her simple yet striking strapless black velvet gown by Atelier Versace, featuring a dramatic thigh-high slit that drew attention to her legs, was more than enough to captivate the audience.
The look quickly went viral, becoming the talk of the town and inspiring countless memes.
At that moment, Jolie became the epitome of sophistication, sexiness, timelessness, and quintessential Hollywood glamour, making her presence undeniably iconic.
Perhaps it wasn't just the dress that left a lasting impression; it was how Jolie carried the entire look.
3. Lady Gaga – 2010 MTV Movie Awards
In a world where most would opt for the most expensive and glamorous designer gowns, Lady Gaga made a bold statement by wearing raw meat, designed by Franc Fernandez, at the 2010 MTV Video Music Awards.
Known for her outrageous red carpet looks, Gaga's 2010 appearance stands out as one of the most controversial, thanks to the impact of her all-flank steak dress on pop culture.
The outfit ignited conversations about fashion, art, and social issues, drawing condemnation from animal rights groups while Gaga explained that it symbolized her fight for individual rights and her distaste for the military's "Don't Ask, Don't Tell" policy.
4. Britney Spears and Justin Timberlake – 2001 AMAs
Believe it or not, Britney Spears and Justin Timberlake once donned all-denim outfits at the 2001 American Music Awards.
While denim is typically associated with casual wear, the former couple made it unforgettable with their matching ensembles, even coordinating their accessories in light blue fabric.
This bold fashion choice sparked a trend at the time, inspired by Spears’ playful suggestion, which costume designer Steven Gerstein later confirmed they fully embraced.
Their iconic look has been frequently mimicked, highlighting its significant cultural impact and enduring legacy in pop fashion history.
5. Halle Berry – 2002 Oscars
Halle Berry left little to the imagination in her stunning Elie Saab dress at the 2002 Oscars, where wearing a high-neck mesh bodice was still quite unusual.
The fitted gown, complete with a flowing taffeta skirt, perfectly complemented Berry’s incredible figure.
In addition to her breathtaking attire, the actress made history that night by becoming the first Black woman to win the Academy Award for Best Actress for her role in Monster’s Ball.
That moment wasn’t just monumental for Berry but also for all the women of color in the industry.
6. Elizabeth Hurley – 1994 Four Weddings and a Funeral Premiere
From a relatively unknown girlfriend of Hugh Grant, Elizabeth Hurley’s daring Gianna Versace gown at the premiere of Four Weddings and a Funeral in 1994 transformed her into a star overnight.
Often described as one of the most significant Versace creations to ever grace the red carpet, the ensemble featured oversized gold safety pins strategically placed to hold the fabric together, emphasizing Hurley’s jaw-dropping figure and becoming a symbol of '90s fashion.
While Grant was already a major star at the time, it was Hurley who captured everyone's attention, making her an unforgettable presence in fashion history.
7. Cher – 1986 Oscars
When Cher was snubbed by the Academy, she made sure to respond in the most glamorous way possible.
At the 1986 Oscars, she collaborated with her longtime designer, Bob Mackie, to create the ultimate "revenge" dress.
Feeling like an outsider, reportedly because the Academy perceived she wasn't "chic enough," Cher donned a stunning black gown adorned with jewels and completed with a dramatic feathered headdress, ensuring she would capture everyone's attention.
True to her intentions, she turned heads that night, and her unforgettable look continues to be remembered and celebrated today.
8. Madonna – 1991 Oscars
Since when has Madonna not been considered an icon? Her every look is iconic, sparking conversations and breaking societal norms.
The Queen of Pop made jaws drop when she donned a Marilyn Monroe-inspired outfit designed by Bob Mackie at the 1991 Oscars.
Madonna embodied modern glamour at that event, wearing a strapless sequined gown with a plunging sweetheart neckline and intricate beading.
She also brought Michael Jackson as her date, solidifying their status as the King and Queen of Pop, though she playfully left some ambiguity about the nature of their relationship.
9. Celine Dion – 1999 Oscars
Celine Dion broke the norms with her John Galliano-designed Dior tuxedo at the 1999 Oscars.
While a man wearing a tuxedo on the red carpet is common, she made it extraordinary by donning the blazer backwards, giving everyone a glimpse of her alluring back.
To say her look was iconic would be an understatement; it established Dion as a trendsetter, boldly defying conventions by opting for pants while other women wore dresses.
“I was the only one with pants in a backward suit from Galliano, and if I would do this today, it would work,” she told People in 2017.
Indeed, Dion's choice was remarkably ahead of its time.
10. Jennifer Lopez – 2000 Grammys
Of course, this list would be incomplete without Jennifer Lopez’s striking green Versace gown at the 2000 Grammys.
Featuring a plunging neckline and a tropical leaf pattern, the dress showcased the Latin superstar’s flawless figure and exuded bold glamour.
This moment was a defining one in fashion history, making her ensemble truly iconic.
In fact, due to her close friendship with Donatella Versace, Lopez closed the Versace Spring-Summer fashion show in Milan in 2019, wearing a near replica of that historic green dress.