The Academy Awards red carpet has long been one of Hollywood’s biggest fashion stages, but it’s also a time capsule. Over the years, audiences have watched their favorite stars grow, experiment, and completely reinvent their style in front of the world.
Some stars arrived at their first Oscars with understated looks that reflected the fashion trends of the time, while their most recent appearances showcase the confidence that comes with years in the spotlight.
While some viewers joked that “some of them looked the same,” others celebrated the transformations, with one comment reading, “I loved each and every one of these. Not one is a miss.”
From fresh-faced debuts to carefully crafted modern appearances, these 17 side-by-side celebrity red carpet moments prove just how much can change between a star’s first Oscars appearance and their latest.
#1 Zendaya, 2015 vs. 2024
When Zendaya first stepped onto the Academy Awards red carpet in 2015, she was just 18 years old and still early in her Hollywood journey.
In fact, the actress later revealed that her debut at the 87th ceremony was essentially a “red carpet crash,” admitting she had no official invite to the ceremony but was determined to show off the look she had reportedly spent the entire night preparing.
For the occasion, she wore an ivory off-the-shoulder Vivienne Westwood gown styled like a modern goddess dress, pairing it with waist-length locs that instantly drew attention.
That hairstyle soon became a defining cultural moment after a racially insensitive remark about her hair from TV host Giuliana Rancic on Fashion Police, who said her hairstyle made her look like she smelled of “patchouli oil or maybe w**d.”
The Challengers star called the remarks “outrageously offensive” and noted they were based on “ignorant slurs and pure disrespect.”
The moment went viral and sparked a larger conversation about representation and respect for natural hair, with many later crediting the incident with helping push awareness that contributed to the CROWN Act, which addresses race-based hair discrimination.
Nearly a decade later, Zendaya returned to the Oscars in a completely different position.
At the 96th Academy Awards in 2024, she attended as an official presenter and one of the night’s biggest fashion highlights.
She walked the carpet in a form-fitted rose-pink and silver silk Armani Privé gown featuring an asymmetrical strap and shimmery palm-tree embroidery.
Zendaya presented the award for Best Cinematography to Hoyte van Hoytema for his work on the film Oppenheimer.
While Zendaya has yet to receive an Oscar nomination herself, her career has flourished since that first appearance.
“Pretty sure this is the moment I fell in love with Zendaya. Still remember the utter disrespect and discrimination she received because of her hair. But she ate this look,” gushed one netizen over her iconic 2015 appearance.
A second user added, “This might be my favourite look of hers. She looks like a goddess.”
“The dress is beautiful but fairly simple, drawing all the attention to her hair and face,” wrote a third.
“The sleek, silky flow of the dress and the structured, voluminous flow of the hair just work together so well. She looked amazing.”
Meanwhile, her 2024 Armani look was dubbed “beautiful, stunning, ethereal, statuesque, sublime.”
“Her blush, lipstick, and earrings all match the pink shade of the dress too—it's perfection,” wrote one user, while another added, “She has a body that literally looks like a fashion sketch in some sort of concept book, so she makes everything look good and somehow arty.”
“The longer I look at it, the more beautiful it gets. It’s a really stunning dress.”
In fact, the actress later revealed that her debut at the 87th ceremony was essentially a “red carpet crash,” admitting she had no official invite to the ceremony but was determined to show off the look she had reportedly spent the entire night preparing.
For the occasion, she wore an ivory off-the-shoulder Vivienne Westwood gown styled like a modern goddess dress, pairing it with waist-length locs that instantly drew attention.
That hairstyle soon became a defining cultural moment after a racially insensitive remark about her hair from TV host Giuliana Rancic on Fashion Police, who said her hairstyle made her look like she smelled of “patchouli oil or maybe w**d.”
The Challengers star called the remarks “outrageously offensive” and noted they were based on “ignorant slurs and pure disrespect.”
The moment went viral and sparked a larger conversation about representation and respect for natural hair, with many later crediting the incident with helping push awareness that contributed to the CROWN Act, which addresses race-based hair discrimination.
Nearly a decade later, Zendaya returned to the Oscars in a completely different position.
At the 96th Academy Awards in 2024, she attended as an official presenter and one of the night’s biggest fashion highlights.
She walked the carpet in a form-fitted rose-pink and silver silk Armani Privé gown featuring an asymmetrical strap and shimmery palm-tree embroidery.
Zendaya presented the award for Best Cinematography to Hoyte van Hoytema for his work on the film Oppenheimer.
While Zendaya has yet to receive an Oscar nomination herself, her career has flourished since that first appearance.
“Pretty sure this is the moment I fell in love with Zendaya. Still remember the utter disrespect and discrimination she received because of her hair. But she ate this look,” gushed one netizen over her iconic 2015 appearance.
A second user added, “This might be my favourite look of hers. She looks like a goddess.”
“The dress is beautiful but fairly simple, drawing all the attention to her hair and face,” wrote a third.
“The sleek, silky flow of the dress and the structured, voluminous flow of the hair just work together so well. She looked amazing.”
Meanwhile, her 2024 Armani look was dubbed “beautiful, stunning, ethereal, statuesque, sublime.”
“Her blush, lipstick, and earrings all match the pink shade of the dress too—it's perfection,” wrote one user, while another added, “She has a body that literally looks like a fashion sketch in some sort of concept book, so she makes everything look good and somehow arty.”
“The longer I look at it, the more beautiful it gets. It’s a really stunning dress.”
14points
#2 Cate Blanchett, 1999 vs. 2023
Cate Blanchett first stepped onto the Academy Awards red carpet in 1999, attending the 71st ceremony as a first-time nominee for Best Actress for her portrayal of Queen Elizabeth I in the hit film Elizabeth.
The Australian star wore a sheer, form-fitting gown designed by John Galliano for Christian Dior.
The dark navy dress featured delicate fabric that draped around her frame, with thin, floral-embroidered straps, a mermaid silhouette, and a deep, round neckline at the front.
However, its most striking detail was the high neckline at the back, featuring intricate hummingbird and floral embroidery across the sheer fabric, which quickly became one of the most memorable looks of the night.
Although Blanchett ultimately lost the Best Actress award to Gwyneth Paltrow for her role in Shakespeare in Love, the nomination established her as one of the industry’s most promising talents.
Blanchett’s most recent Oscar appearance came at the 95th Academy Awards in 2023.
This time, she attended as a nominee for Best Actress for her critically acclaimed performance as Lydia Tár in Tár.
For the occasion, the actress opted for an archival ensemble from Louis Vuitton, consisting of a striking teal silk capelet top with bold shoulder pads paired with a sleek black velvet skirt featuring a dramatic train.
The look also reflected Blanchett’s long-standing commitment to sustainable fashion, as the teal top was drawn from the brand’s archival collection rather than being newly created.
Although she was widely praised for her performance in Tár, Blanchett ultimately lost the award to Michelle Yeoh.
In a nod to the memorable Oscars look, Blanchett later re-wore the same structured teal top exactly one year later at the Louis Vuitton Fall/Winter 2024 show in Paris, further highlighting her advocacy for sustainable fashion.
One fan of the actress’s style across both Oscar appearances wrote online, “She just exudes cool. There’s so much variety in her fashion over the years and she pulls everything off.”
Another commenter said, “I love her re-wears and seeing which new accessories she adds each time. It helps that everything she wears is tailored to perfection.”
“I love everything about her looks, and the fact that she buys and then rewears her clothes is just the icing on the cake,” admired another netizen.
“She's always beautiful, and there's something so statuesque about her frame and face that helps her pull off everything. Just a beautiful work of art.”
The Australian star wore a sheer, form-fitting gown designed by John Galliano for Christian Dior.
The dark navy dress featured delicate fabric that draped around her frame, with thin, floral-embroidered straps, a mermaid silhouette, and a deep, round neckline at the front.
However, its most striking detail was the high neckline at the back, featuring intricate hummingbird and floral embroidery across the sheer fabric, which quickly became one of the most memorable looks of the night.
Although Blanchett ultimately lost the Best Actress award to Gwyneth Paltrow for her role in Shakespeare in Love, the nomination established her as one of the industry’s most promising talents.
Blanchett’s most recent Oscar appearance came at the 95th Academy Awards in 2023.
This time, she attended as a nominee for Best Actress for her critically acclaimed performance as Lydia Tár in Tár.
For the occasion, the actress opted for an archival ensemble from Louis Vuitton, consisting of a striking teal silk capelet top with bold shoulder pads paired with a sleek black velvet skirt featuring a dramatic train.
The look also reflected Blanchett’s long-standing commitment to sustainable fashion, as the teal top was drawn from the brand’s archival collection rather than being newly created.
Although she was widely praised for her performance in Tár, Blanchett ultimately lost the award to Michelle Yeoh.
In a nod to the memorable Oscars look, Blanchett later re-wore the same structured teal top exactly one year later at the Louis Vuitton Fall/Winter 2024 show in Paris, further highlighting her advocacy for sustainable fashion.
One fan of the actress’s style across both Oscar appearances wrote online, “She just exudes cool. There’s so much variety in her fashion over the years and she pulls everything off.”
Another commenter said, “I love her re-wears and seeing which new accessories she adds each time. It helps that everything she wears is tailored to perfection.”
“I love everything about her looks, and the fact that she buys and then rewears her clothes is just the icing on the cake,” admired another netizen.
“She's always beautiful, and there's something so statuesque about her frame and face that helps her pull off everything. Just a beautiful work of art.”
13points
#3 Margot Robbie, 2014 vs. 2024
When Margot Robbie first attended the Academy Awards in 2014, she was still riding the massive success of her breakout role in The Wolf of Wall Street.
The film, directed by Martin Scorsese and starring Leonardo DiCaprio, earned five nominations at the 86th ceremony, including Best Picture, and Robbie attended the event as part of the celebrated cast.
For her first Oscars red carpet appearance, the Australian actress stunned in a strapless black Saint Laurent gown featuring a sleek silhouette and a matching bow detail at the back.
However, what truly caught fans’ attention was her dramatic hair transformation.
Known for her bright blonde locks, Robbie instead arrived at the ceremony with jet-black hair, a change she made for her role in the upcoming film Z for Zachariah.
The striking look left many fans saying she was nearly “unrecognizable” on the red carpet.
Although Robbie did not present or win an award that year, the appearance marked one of her earliest moments on Hollywood’s biggest stage.
A decade later, in 2024, Margot marked her most recent Oscars appearance as of early 2026.
She attended the ceremony as both a presenter and a Best Picture nominee thanks to her role as a producer on the global blockbuster Barbie, which ultimately lost to Oppenheimer.
For the occasion, she wore a shimmering black chainmail gown from Versace’s Fall/Winter 2024 collection.
The look stood out even more because it broke from the actress’s months-long “method dressing” streak as Barbie, during which she paid tribute to the iconic doll with a parade of pink ensembles throughout the awards season.
One netizen expressed disappointment over her 2024 look, writing, “She’s always gonna look good, but compare this to every other award look she has worn this season and every Barbie press look she has turned out. This is shockingly simple and devoid of color in comparison to the image she has been otherwise cultivating up until now.”
A second chimed in, “It looks like a melted peplum, and yet if anyone can pull that off, it's her.”
Meanwhile, one fan of the look said, “Sheesh, I’m the only one who likes the dress?? The only thing I would change is the hair, but I think she looks amazing!”
Others in agreement added, “I LOVE it. She looks stunning as per usual. She looks gracious too by going so simple.”
The film, directed by Martin Scorsese and starring Leonardo DiCaprio, earned five nominations at the 86th ceremony, including Best Picture, and Robbie attended the event as part of the celebrated cast.
For her first Oscars red carpet appearance, the Australian actress stunned in a strapless black Saint Laurent gown featuring a sleek silhouette and a matching bow detail at the back.
However, what truly caught fans’ attention was her dramatic hair transformation.
Known for her bright blonde locks, Robbie instead arrived at the ceremony with jet-black hair, a change she made for her role in the upcoming film Z for Zachariah.
The striking look left many fans saying she was nearly “unrecognizable” on the red carpet.
Although Robbie did not present or win an award that year, the appearance marked one of her earliest moments on Hollywood’s biggest stage.
A decade later, in 2024, Margot marked her most recent Oscars appearance as of early 2026.
She attended the ceremony as both a presenter and a Best Picture nominee thanks to her role as a producer on the global blockbuster Barbie, which ultimately lost to Oppenheimer.
For the occasion, she wore a shimmering black chainmail gown from Versace’s Fall/Winter 2024 collection.
The look stood out even more because it broke from the actress’s months-long “method dressing” streak as Barbie, during which she paid tribute to the iconic doll with a parade of pink ensembles throughout the awards season.
One netizen expressed disappointment over her 2024 look, writing, “She’s always gonna look good, but compare this to every other award look she has worn this season and every Barbie press look she has turned out. This is shockingly simple and devoid of color in comparison to the image she has been otherwise cultivating up until now.”
A second chimed in, “It looks like a melted peplum, and yet if anyone can pull that off, it's her.”
Meanwhile, one fan of the look said, “Sheesh, I’m the only one who likes the dress?? The only thing I would change is the hair, but I think she looks amazing!”
Others in agreement added, “I LOVE it. She looks stunning as per usual. She looks gracious too by going so simple.”
12points
#4 Meryl Streep, 1979 vs. 2018
Meryl Streep first attended the Academy Awards in 1979 as a rising star who had just earned her first Oscar nomination for Best Supporting Actress for her role as Linda in the acclaimed Vietnam War drama The Deer Hunter.
It marked the beginning of what would eventually become the most-nominated acting career in the history of the ceremony, as Streep currently holds a total of 21 nominations.
For her debut at the 51st Academy Awards, Streep opted for a floor-length black gown with long, flouncy sleeves and a sheer-patterned mesh neckline.
The elegant yet understated look reflected the classic red carpet style of the late ’70s. Interestingly, the actress later recycled the exact same dress three decades later when she attended the BAFTA Awards in 2009.
Streep attended the ceremony with her then-husband, sculptor Don Gummer, and the night carried emotional weight, as her partner and co-star John Cazale had passed away from cancer just months before the film’s release.
Although Streep ultimately lost the award that year to Maggie Smith, the nomination marked the beginning of a legendary Oscars journey.
Nearly four decades later, Streep returned to the ceremony for what remains her most recent appearance in 2018.
At the 90th Academy Awards, she was nominated for Best Actress for her portrayal of newspaper publisher Kay Graham in The Post.
For the occasion, Streep opted for a deep-red custom Christian Dior Haute Couture gown featuring a plunging V-neckline and long sleeves.
Although she did not take home the award that night, losing to Frances McDormand for her role in Three Billboards Outside Ebbing, Missouri, her presence was widely celebrated by fans.
One person gushed online, “WOW! Meryl Streep is such a true beauty, just flawless… she's like fine wine. Gets better as time passes.”
“Totally agree. It’s Meryl Streep. She always looks classy and can wear whatever she wants. I’m always happy to see her,” said another, while a third added, “She always looks rich. Like she has a summer house on the Cape and winters in Palm Springs.”
“I love her! She always looks polished, elegant, and beautiful. But more than that, she always looks like she's having fun - like she's happy to be there, and it's not just a job to her. That's refreshing when compared to some other actors.”
It marked the beginning of what would eventually become the most-nominated acting career in the history of the ceremony, as Streep currently holds a total of 21 nominations.
For her debut at the 51st Academy Awards, Streep opted for a floor-length black gown with long, flouncy sleeves and a sheer-patterned mesh neckline.
The elegant yet understated look reflected the classic red carpet style of the late ’70s. Interestingly, the actress later recycled the exact same dress three decades later when she attended the BAFTA Awards in 2009.
Streep attended the ceremony with her then-husband, sculptor Don Gummer, and the night carried emotional weight, as her partner and co-star John Cazale had passed away from cancer just months before the film’s release.
Although Streep ultimately lost the award that year to Maggie Smith, the nomination marked the beginning of a legendary Oscars journey.
Nearly four decades later, Streep returned to the ceremony for what remains her most recent appearance in 2018.
At the 90th Academy Awards, she was nominated for Best Actress for her portrayal of newspaper publisher Kay Graham in The Post.
For the occasion, Streep opted for a deep-red custom Christian Dior Haute Couture gown featuring a plunging V-neckline and long sleeves.
Although she did not take home the award that night, losing to Frances McDormand for her role in Three Billboards Outside Ebbing, Missouri, her presence was widely celebrated by fans.
One person gushed online, “WOW! Meryl Streep is such a true beauty, just flawless… she's like fine wine. Gets better as time passes.”
“Totally agree. It’s Meryl Streep. She always looks classy and can wear whatever she wants. I’m always happy to see her,” said another, while a third added, “She always looks rich. Like she has a summer house on the Cape and winters in Palm Springs.”
“I love her! She always looks polished, elegant, and beautiful. But more than that, she always looks like she's having fun - like she's happy to be there, and it's not just a job to her. That's refreshing when compared to some other actors.”
9points
#5 Meg Ryan, 1998 vs. 2025
When Meg Ryan first stepped onto the Academy Awards red carpet in 1998, she was at the height of her reign as Hollywood’s beloved romantic-comedy star.
The actress attended the 70th ceremony as a presenter during a particularly successful period in her career, having recently starred in the animated musical Anastasia and preparing for the release of the hit rom-com You've Got Mail.
For the occasion, Ryan wore a high-neck, long-sleeved black gown designed by Vera Wang, pairing the elegant look with distinctive rose-tinted tiny sunglasses that perfectly captured late ’90s fashion trends.
She arrived alongside her then-husband, Dennis Quaid, with the pair turning heads in coordinated all-black outfits and dark shades.
During the ceremony, Ryan took the stage to present the award for Best Art Direction, which ultimately went to Titanic.
After a 27-year hiatus from the prestigious event, Ryan returned to the Oscars for her most recent appearance at the 97th Academy Awards in 2025.
For the milestone comeback, the actress wore a custom strapless red velvet gown by Ashi Studio featuring dramatic thigh-high slits, creating one of the evening’s most striking red-carpet looks.
Ryan also shared one of the night’s most nostalgic moments when she reunited on stage with her When Harry Met Sally co-star Billy Crystal.
The duo walked out to the classic song It Had to Be You and exchanged playful banter referencing their beloved 1989 film before presenting the award for Best Picture to Anora.
Meg’s return to the Oscars nearly three decades later sparked significant conversation online, and not solely for positive reasons.
While many fans celebrated her “triumphant return” to the ceremony, others on social media engaged in intense speculation about cosmetic procedures, citing noticeable changes in her appearance.
One critic noted, “Looking at Meg Ryan and Billy Crystal. He looks like a normal guy his age - great. But Meg just looks like all the work on her face went horribly wrong. Very sad.”
A second user in agreement said, “Meg Ryan is exhibit A why you don't mess with a beautiful face as you get older.”
A third bluntly added, “She removed everything that made her uniquely adorable.”
Another commenter wrote, “Meg Ryan too. Their faces are so immobile they look strange when they speak or smile…”
Although Ryan has never been nominated for an Oscar herself, her lasting legacy in the romantic-comedy genre continues to make her one of the most recognizable stars of her generation.
The actress attended the 70th ceremony as a presenter during a particularly successful period in her career, having recently starred in the animated musical Anastasia and preparing for the release of the hit rom-com You've Got Mail.
For the occasion, Ryan wore a high-neck, long-sleeved black gown designed by Vera Wang, pairing the elegant look with distinctive rose-tinted tiny sunglasses that perfectly captured late ’90s fashion trends.
She arrived alongside her then-husband, Dennis Quaid, with the pair turning heads in coordinated all-black outfits and dark shades.
During the ceremony, Ryan took the stage to present the award for Best Art Direction, which ultimately went to Titanic.
After a 27-year hiatus from the prestigious event, Ryan returned to the Oscars for her most recent appearance at the 97th Academy Awards in 2025.
For the milestone comeback, the actress wore a custom strapless red velvet gown by Ashi Studio featuring dramatic thigh-high slits, creating one of the evening’s most striking red-carpet looks.
Ryan also shared one of the night’s most nostalgic moments when she reunited on stage with her When Harry Met Sally co-star Billy Crystal.
The duo walked out to the classic song It Had to Be You and exchanged playful banter referencing their beloved 1989 film before presenting the award for Best Picture to Anora.
Meg’s return to the Oscars nearly three decades later sparked significant conversation online, and not solely for positive reasons.
While many fans celebrated her “triumphant return” to the ceremony, others on social media engaged in intense speculation about cosmetic procedures, citing noticeable changes in her appearance.
One critic noted, “Looking at Meg Ryan and Billy Crystal. He looks like a normal guy his age - great. But Meg just looks like all the work on her face went horribly wrong. Very sad.”
A second user in agreement said, “Meg Ryan is exhibit A why you don't mess with a beautiful face as you get older.”
A third bluntly added, “She removed everything that made her uniquely adorable.”
Another commenter wrote, “Meg Ryan too. Their faces are so immobile they look strange when they speak or smile…”
Although Ryan has never been nominated for an Oscar herself, her lasting legacy in the romantic-comedy genre continues to make her one of the most recognizable stars of her generation.
9points
#6 Nicole Kidman, 1991 vs. 2023
When Nicole Kidman first attended the Academy Awards in 1991, she was still a rising Australian actress just beginning to break into Hollywood.
At the time, she had recently starred opposite her ex-husband Tom Cruise in the racing drama Days of Thunder, which marked her first major American film role.
Kidman made her Oscars debut as Cruise’s guest while he served as a presenter that evening.
For the occasion, she wore a simple black velvet minidress featuring ornate, bejeweled silver trim, paired with her signature curly red hair.
The understated look reflected the more relaxed red carpet style of the early ’90s, long before elaborate styling became the norm.
Over the decades that followed, she would go on to become one of the industry’s most celebrated actresses, earning multiple nominations and eventually winning an Oscar for her performance in The Hours.
More than three decades later, Kidman made her most recent Oscars appearance at the 95th Academy Awards in 2023.
This time, she attended as an official presenter, taking the stage to award Best Director to Daniel Kwan and Daniel Scheinert for their acclaimed film Everything Everywhere All at Once.
For the evening, Kidman opted for a custom shimmering black Armani Privé gown featuring a dramatic thigh-high slit and two large 3D silver-and-black floral appliqués, one placed on her shoulder and the other on her hip.
The actress also made headlines for sharing affectionate moments on the red carpet with her second ex-husband, country star Keith Urban.
One fashion enthusiast wrote, admiring her understated 1991 look, “I love Love LOVE this dress, even now,” while another added, “I was a kid when she wore this and I still remember it. It was so beautiful on her.”
“Nicole with natural curls > Nicole with straight hair and wigs. Otherwise, A+, knocks it out of the park.”
Others gushed over her shimmering Armani gown, with one fan writing online, “I don't care much for celebrity fashion, but when she walked the red carpet in this - wow. This dress, her styling, it was perfection.”
A second user commented, “She is an absolute diva. She can carry any look honestly. I love love love the dress she wore.”
“She is timeless… always fabulous and ages so gracefully.”
At the time, she had recently starred opposite her ex-husband Tom Cruise in the racing drama Days of Thunder, which marked her first major American film role.
Kidman made her Oscars debut as Cruise’s guest while he served as a presenter that evening.
For the occasion, she wore a simple black velvet minidress featuring ornate, bejeweled silver trim, paired with her signature curly red hair.
The understated look reflected the more relaxed red carpet style of the early ’90s, long before elaborate styling became the norm.
Over the decades that followed, she would go on to become one of the industry’s most celebrated actresses, earning multiple nominations and eventually winning an Oscar for her performance in The Hours.
More than three decades later, Kidman made her most recent Oscars appearance at the 95th Academy Awards in 2023.
This time, she attended as an official presenter, taking the stage to award Best Director to Daniel Kwan and Daniel Scheinert for their acclaimed film Everything Everywhere All at Once.
For the evening, Kidman opted for a custom shimmering black Armani Privé gown featuring a dramatic thigh-high slit and two large 3D silver-and-black floral appliqués, one placed on her shoulder and the other on her hip.
The actress also made headlines for sharing affectionate moments on the red carpet with her second ex-husband, country star Keith Urban.
One fashion enthusiast wrote, admiring her understated 1991 look, “I love Love LOVE this dress, even now,” while another added, “I was a kid when she wore this and I still remember it. It was so beautiful on her.”
“Nicole with natural curls > Nicole with straight hair and wigs. Otherwise, A+, knocks it out of the park.”
Others gushed over her shimmering Armani gown, with one fan writing online, “I don't care much for celebrity fashion, but when she walked the red carpet in this - wow. This dress, her styling, it was perfection.”
A second user commented, “She is an absolute diva. She can carry any look honestly. I love love love the dress she wore.”
“She is timeless… always fabulous and ages so gracefully.”
8points
#7 Demi Moore, 1989 vs. 2025
When Demi Moore first stepped onto the Academy Awards red carpet in 1989, she was already a rising Hollywood star known for pushing fashion boundaries.
The actress attended the 61st ceremony alongside her then-husband, action star Bruce Willis, with the pair presenting the award for Best Cinematography.
Moore’s outfit that night quickly became one of the most talked-about looks in Oscars history.
Instead of wearing a traditional designer gown, she famously created her own DIY ensemble featuring a corset-style top, lace-trimmed spandex bike shorts, and a metallic cape-like half-skirt.
During the ceremony, Moore presented the award for Best Cinematography to Peter Biziou for his work on the film Mississippi Burning.
Moore made her most recent appearance at the Oscars during the 97th Academy Awards in 2025, which she attended as a first-time Best Actress nominee for her performance in the provocative body-horror film The Substance.
For the milestone moment, Moore wore a custom shimmering silver Giorgio Armani Privé gown featuring intricate crystal embroidery, a plunging neckline, and structured pleats at the hips that flowed into a short train.
Although Moore ultimately lost the Best Actress award to Mikey Madison for her performance in Anora, the nomination itself was widely celebrated.
The moment was often described by fans as part of the actress’s long-awaited “Demissance,” a career resurgence that recognized her four decades of work in Hollywood.
She attended the ceremony with longtime stylist Brad Goreski, who helped craft her carefully curated “method dressing” press tour for The Substance.
While her silver gown was widely praised, with some fans saying it made her look “radiant” and others claiming to be “obsessed” with the dress, Demi’s unconventional 1989 design had stunned viewers and critics alike, landing her on numerous “worst-dressed” lists at the time.
However, decades later, fashion commentators have revisited the bold look with a different perspective.
Many now view the outfit as a surprisingly ahead-of-its-time moment. Several viewers agreed, “It’s giving Liberace somehow. I kinda love it. Just wish the shorts had that same black patterning as the rest and maybe some gold detail.”
Another netizen wrote, “It’s sad that actresses no longer experiment with their dressing on the Oscar’s red carpet... If Moore designed this herself props to her! At least she was being creative!”
“As a bike shorts devotee, I endorse this look. It’s very authentic, f*ck it. I like it.”
Others echoed the sentiment, “This was peak ugly then. It was such a big deal. Like how dare beautiful Demi wear such a thing! I thought it looked stupid then but now I kinda like it.”
The actress attended the 61st ceremony alongside her then-husband, action star Bruce Willis, with the pair presenting the award for Best Cinematography.
Moore’s outfit that night quickly became one of the most talked-about looks in Oscars history.
Instead of wearing a traditional designer gown, she famously created her own DIY ensemble featuring a corset-style top, lace-trimmed spandex bike shorts, and a metallic cape-like half-skirt.
During the ceremony, Moore presented the award for Best Cinematography to Peter Biziou for his work on the film Mississippi Burning.
Moore made her most recent appearance at the Oscars during the 97th Academy Awards in 2025, which she attended as a first-time Best Actress nominee for her performance in the provocative body-horror film The Substance.
For the milestone moment, Moore wore a custom shimmering silver Giorgio Armani Privé gown featuring intricate crystal embroidery, a plunging neckline, and structured pleats at the hips that flowed into a short train.
Although Moore ultimately lost the Best Actress award to Mikey Madison for her performance in Anora, the nomination itself was widely celebrated.
The moment was often described by fans as part of the actress’s long-awaited “Demissance,” a career resurgence that recognized her four decades of work in Hollywood.
She attended the ceremony with longtime stylist Brad Goreski, who helped craft her carefully curated “method dressing” press tour for The Substance.
While her silver gown was widely praised, with some fans saying it made her look “radiant” and others claiming to be “obsessed” with the dress, Demi’s unconventional 1989 design had stunned viewers and critics alike, landing her on numerous “worst-dressed” lists at the time.
However, decades later, fashion commentators have revisited the bold look with a different perspective.
Many now view the outfit as a surprisingly ahead-of-its-time moment. Several viewers agreed, “It’s giving Liberace somehow. I kinda love it. Just wish the shorts had that same black patterning as the rest and maybe some gold detail.”
Another netizen wrote, “It’s sad that actresses no longer experiment with their dressing on the Oscar’s red carpet... If Moore designed this herself props to her! At least she was being creative!”
“As a bike shorts devotee, I endorse this look. It’s very authentic, f*ck it. I like it.”
Others echoed the sentiment, “This was peak ugly then. It was such a big deal. Like how dare beautiful Demi wear such a thing! I thought it looked stupid then but now I kinda like it.”
8points
#8 Robert Downey Jr., 1989 vs. 2025
Robert Downey Jr. first appeared on the Academy Awards red carpet in 1989 as the date of his then-girlfriend, Sarah Jessica Parker, with the young couple quickly becoming one of the most talked-about pairs of the evening.
At the time, Downey Jr. had recently gained widespread recognition for his performance in the 1987 drama Less Than Zero.
For his Oscars debut, he opted for an oversized black tuxedo complete with delicate embroidery on the lapels, a style that reflected the relaxed tailoring trends popular during the late 1980s.
Although he did not present or receive any awards during the ceremony, the appearance marked one of Downey Jr.’s earliest moments on Hollywood’s biggest red carpet.
His most recent appearance came at the 97th Academy Awards in 2025, where he served as an official presenter, returning to the ceremony as a reigning Oscar winner.
For the occasion, the actor wore a custom black Gucci tuxedo featuring a single-breasted jacket with peak lapels and subtly flared trousers.
He paired the suit with a black shirt, tinted spectacles, and a distinctive brooch from the Tiffany & Co. archives designed by Jean Schlumberger.
The 60-year-old actor attended the ceremony with his wife, Susan Downey, and the couple drew praise for their charming chemistry on the red carpet. They were frequently seen holding hands and laughing together as they posed for photographers.
During the ceremony, Downey Jr. took the stage to present the award for Best Supporting Actor, which ultimately went to Kieran Culkin for his performance in A Real Pain.
In his acceptance speech, Culkin even gave a special shoutout to Downey Jr., addressing him as “Mr. Downey, sir” and noting that receiving the award from the veteran actor meant a great deal to him.
Netizens were divided over the actor’s evolving style on the Oscars red carpet.
One admirer wrote, “Some men get better looking as they age! *cough Robert Downey Jr cough*.”
Meanwhile, a fashion critic commented, “When did men start dressing so flamboyantly for the Oscars? For the longest time, guys just wore black tuxedos and bow ties. Then you’d occasionally get someone in a more relaxed look like Robert Downey Jr. now it seems [he’s] wearing high-fashion tuxedos in bold colors or experimental fits.”
At the time, Downey Jr. had recently gained widespread recognition for his performance in the 1987 drama Less Than Zero.
For his Oscars debut, he opted for an oversized black tuxedo complete with delicate embroidery on the lapels, a style that reflected the relaxed tailoring trends popular during the late 1980s.
Although he did not present or receive any awards during the ceremony, the appearance marked one of Downey Jr.’s earliest moments on Hollywood’s biggest red carpet.
His most recent appearance came at the 97th Academy Awards in 2025, where he served as an official presenter, returning to the ceremony as a reigning Oscar winner.
For the occasion, the actor wore a custom black Gucci tuxedo featuring a single-breasted jacket with peak lapels and subtly flared trousers.
He paired the suit with a black shirt, tinted spectacles, and a distinctive brooch from the Tiffany & Co. archives designed by Jean Schlumberger.
The 60-year-old actor attended the ceremony with his wife, Susan Downey, and the couple drew praise for their charming chemistry on the red carpet. They were frequently seen holding hands and laughing together as they posed for photographers.
During the ceremony, Downey Jr. took the stage to present the award for Best Supporting Actor, which ultimately went to Kieran Culkin for his performance in A Real Pain.
In his acceptance speech, Culkin even gave a special shoutout to Downey Jr., addressing him as “Mr. Downey, sir” and noting that receiving the award from the veteran actor meant a great deal to him.
Netizens were divided over the actor’s evolving style on the Oscars red carpet.
One admirer wrote, “Some men get better looking as they age! *cough Robert Downey Jr cough*.”
Meanwhile, a fashion critic commented, “When did men start dressing so flamboyantly for the Oscars? For the longest time, guys just wore black tuxedos and bow ties. Then you’d occasionally get someone in a more relaxed look like Robert Downey Jr. now it seems [he’s] wearing high-fashion tuxedos in bold colors or experimental fits.”
8points
#9 Marlee Matlin, 1987 vs. 2025
When Marlee Matlin first stepped onto the Academy Awards red carpet in 1987, she was a 21-year-old newcomer and a nominee for Best Actress for her performance in Children of a Lesser God.
For the occasion, Matlin wore a lavender gown designed by Theadora Van Runkle, featuring delicate lace detailing and a plunging V-neckline, with full sleeves and a matching purple satin waistband.
She completed the elegant look with baby’s breath flowers tucked into her hair and her black-rimmed glasses.
The night turned historic when Matlin won the Oscar for Best Actress, making her both the youngest winner in the category’s history and the first Deaf performer to win an Academy Award.
During the ceremony, she also presented the award for Best Sound using American Sign Language, with an interpreter speaking her words for the audience.
During the COVID-19 pandemic in March 2020, Matlin delighted fans by rewearing the original 1987 lavender gown, revealing that she had rediscovered it in her closet while “spring cleaning.”
She posted a video to social media showing that the dress still fit perfectly 33 years later as she posed with her original Oscar statuette.
Nearly four decades later, Matlin returned to the Oscars for her most recent appearance at the 97th Academy Awards in 2025.
This time, she attended in her official capacity as a governor of the Academy of Motion Picture Arts and Sciences, reflecting her continued leadership within the film industry.
She was reelected to represent the Actors Branch on the organization’s Board of Governors for the 2025-2026 term, having first joined the board in 2022.
For the occasion, the actress wore a custom Yara Shoemaker Fall/Winter 2024-25 Haute Couture floor-length gown featuring intricate sheer mesh and beadwork detailing, paired with elegant jewelry from Briony Raymond New York.
Although Matlin did not receive a competitive award during the ceremony, she had recently been honored at the Academy’s 2025 Scientific and Technical Awards, where she accepted an Academy Award of Merit recognizing her long-standing advocacy for captioning technology and accessibility in film.
For the occasion, Matlin wore a lavender gown designed by Theadora Van Runkle, featuring delicate lace detailing and a plunging V-neckline, with full sleeves and a matching purple satin waistband.
She completed the elegant look with baby’s breath flowers tucked into her hair and her black-rimmed glasses.
The night turned historic when Matlin won the Oscar for Best Actress, making her both the youngest winner in the category’s history and the first Deaf performer to win an Academy Award.
During the ceremony, she also presented the award for Best Sound using American Sign Language, with an interpreter speaking her words for the audience.
During the COVID-19 pandemic in March 2020, Matlin delighted fans by rewearing the original 1987 lavender gown, revealing that she had rediscovered it in her closet while “spring cleaning.”
She posted a video to social media showing that the dress still fit perfectly 33 years later as she posed with her original Oscar statuette.
Nearly four decades later, Matlin returned to the Oscars for her most recent appearance at the 97th Academy Awards in 2025.
This time, she attended in her official capacity as a governor of the Academy of Motion Picture Arts and Sciences, reflecting her continued leadership within the film industry.
She was reelected to represent the Actors Branch on the organization’s Board of Governors for the 2025-2026 term, having first joined the board in 2022.
For the occasion, the actress wore a custom Yara Shoemaker Fall/Winter 2024-25 Haute Couture floor-length gown featuring intricate sheer mesh and beadwork detailing, paired with elegant jewelry from Briony Raymond New York.
Although Matlin did not receive a competitive award during the ceremony, she had recently been honored at the Academy’s 2025 Scientific and Technical Awards, where she accepted an Academy Award of Merit recognizing her long-standing advocacy for captioning technology and accessibility in film.
8points
#10 Jennifer Lopez, 1997 vs. 2019
When Jennifer Lopez first attended the Academy Awards in 1997, she was promoting her breakout film Selena, which had been released only days before the ceremony.
Her performance as the beloved Tejano singer had already generated massive buzz across the industry.
For her first Oscars appearance, Lopez wore a lacy, form-fitting Badgley Mischka gown.
The dress featured a sheer bodice adorned with intricate silver beaded floral embroidery, which flowed into a floor-length skirt that beautifully highlighted her curves.
Although Lopez was not nominated that year, she still had an important role in the ceremony.
She presented the award for Best Original Score, which ultimately went to Rachel Portman for the film Emma.
Lopez’s most recent Oscars appearance came in 2019, when she attended alongside her then-fiancé, former baseball star Alex Rodriguez.
She appeared as an A-list presenter during a year when she was actively promoting her film Second Act and continuing to dominate both the music and film industries.
For the occasion, Lopez turned heads in a striking high-neck, long-sleeved Tom Ford gown made entirely of mirrored mosaic tiles.
The dazzling design created a shattered-glass effect under the lights, quickly becoming one of the most memorable fashion moments of the evening.
During the ceremony, Lopez presented the award for Best Production Design alongside Chris Evans, with the prize going to the Marvel blockbuster Black Panther.
Many netizens dubbed J.Lo “the most beautiful when she was young” while discussing her first Oscars appearance.
One fan admired, “[The dress] is so sleek and chic without being boring, and fits her like an absolute glove.”
Another expressed, “That hair was goals when she did that. I remember I achieved it once where it didn’t deflate.”
A third person said, “I was a child in the ’90s, so that probably influenced my particular bias toward that aesthetic/vibe. I love all the satin looks! I love that the era was glamorous… It was just such a special time for fashion.”
“There's something so memorable about that look for me. Seeing it immediately brought me back to that place and time!”
Her performance as the beloved Tejano singer had already generated massive buzz across the industry.
For her first Oscars appearance, Lopez wore a lacy, form-fitting Badgley Mischka gown.
The dress featured a sheer bodice adorned with intricate silver beaded floral embroidery, which flowed into a floor-length skirt that beautifully highlighted her curves.
Although Lopez was not nominated that year, she still had an important role in the ceremony.
She presented the award for Best Original Score, which ultimately went to Rachel Portman for the film Emma.
Lopez’s most recent Oscars appearance came in 2019, when she attended alongside her then-fiancé, former baseball star Alex Rodriguez.
She appeared as an A-list presenter during a year when she was actively promoting her film Second Act and continuing to dominate both the music and film industries.
For the occasion, Lopez turned heads in a striking high-neck, long-sleeved Tom Ford gown made entirely of mirrored mosaic tiles.
The dazzling design created a shattered-glass effect under the lights, quickly becoming one of the most memorable fashion moments of the evening.
During the ceremony, Lopez presented the award for Best Production Design alongside Chris Evans, with the prize going to the Marvel blockbuster Black Panther.
Many netizens dubbed J.Lo “the most beautiful when she was young” while discussing her first Oscars appearance.
One fan admired, “[The dress] is so sleek and chic without being boring, and fits her like an absolute glove.”
Another expressed, “That hair was goals when she did that. I remember I achieved it once where it didn’t deflate.”
A third person said, “I was a child in the ’90s, so that probably influenced my particular bias toward that aesthetic/vibe. I love all the satin looks! I love that the era was glamorous… It was just such a special time for fashion.”
“There's something so memorable about that look for me. Seeing it immediately brought me back to that place and time!”
7points
#11 Ralph Fiennes, 1994 vs. 2025
When Ralph Fiennes made his Academy Awards red carpet debut in 1994, he was a breakout star whose chilling performance had already made a huge impression on Hollywood.
The British actor attended the 66th ceremony as a first-time nominee for Best Supporting Actor for his role as N**i commandant Amon Göth in Schindler's List.
At just 31 years old, Fiennes was widely considered one of the biggest discoveries of the year.
His unsettling portrayal of Göth was so powerful that the character later earned a place on the American Film Institute’s list of the greatest film villains of all time.
Fiennes opted for a classic black tuxedo paired with a crisp white shirt and a traditional black bow tie, an elegant look fitting for Hollywood’s biggest night.
Although Schindler's List dominated the ceremony with multiple awards, Fiennes ultimately lost the Best Supporting Actor trophy to Tommy Lee Jones for his performance in The Fugitive.
Still, the nomination instantly cemented Fiennes as one of the most compelling actors of his generation.
More than three decades later, Fiennes returned to the Oscars for his most recent appearance at the 97th Academy Awards in 2025.
This time, he attended as a nominee for Best Actor in a Leading Role for his performance as Cardinal Lawrence in the Vatican-set thriller Conclave.
For the occasion, the actor once again embraced a timeless style, walking the red carpet in a classic black tuxedo.
He was joined by his Conclave co-stars Isabella Rossellini and John Lithgow, with the trio drawing attention as one of the film’s standout ensembles of the year.
However, the night later sparked controversy after it emerged that some Academy of Motion Picture Arts and Sciences voters had mistakenly believed Fiennes had already won an Oscar for Schindler’s List, leading them not to vote for him.
The Best Actor award ultimately went to Adrien Brody for his performance in The Brutalist.
Despite earning multiple nominations and portraying iconic characters like Lord Voldemort in the Harry Potter film series and M in the James Bond franchise during the No Time to Die era, Fiennes has yet to win a competitive Academy Award.
The British actor attended the 66th ceremony as a first-time nominee for Best Supporting Actor for his role as N**i commandant Amon Göth in Schindler's List.
At just 31 years old, Fiennes was widely considered one of the biggest discoveries of the year.
His unsettling portrayal of Göth was so powerful that the character later earned a place on the American Film Institute’s list of the greatest film villains of all time.
Fiennes opted for a classic black tuxedo paired with a crisp white shirt and a traditional black bow tie, an elegant look fitting for Hollywood’s biggest night.
Although Schindler's List dominated the ceremony with multiple awards, Fiennes ultimately lost the Best Supporting Actor trophy to Tommy Lee Jones for his performance in The Fugitive.
Still, the nomination instantly cemented Fiennes as one of the most compelling actors of his generation.
More than three decades later, Fiennes returned to the Oscars for his most recent appearance at the 97th Academy Awards in 2025.
This time, he attended as a nominee for Best Actor in a Leading Role for his performance as Cardinal Lawrence in the Vatican-set thriller Conclave.
For the occasion, the actor once again embraced a timeless style, walking the red carpet in a classic black tuxedo.
He was joined by his Conclave co-stars Isabella Rossellini and John Lithgow, with the trio drawing attention as one of the film’s standout ensembles of the year.
However, the night later sparked controversy after it emerged that some Academy of Motion Picture Arts and Sciences voters had mistakenly believed Fiennes had already won an Oscar for Schindler’s List, leading them not to vote for him.
The Best Actor award ultimately went to Adrien Brody for his performance in The Brutalist.
Despite earning multiple nominations and portraying iconic characters like Lord Voldemort in the Harry Potter film series and M in the James Bond franchise during the No Time to Die era, Fiennes has yet to win a competitive Academy Award.
6points
#12 Dwayne Johnson, 2008 vs. 2024
When Dwayne Johnson first stepped onto the Academy Awards red carpet in 2008, he was already a global celebrity beginning his transition from professional wrestling into a major Hollywood star.
The actor, widely known as “The Rock,” attended the 80th ceremony as an invited presenter, marking a significant milestone in his growing film career.
For the occasion, Johnson wore a classic black tuxedo paired with a crisp white shirt and a traditional black bow tie, embracing the formal style expected at the high-profile event.
During the ceremony, Johnson presented the award for Best Visual Effects, which ultimately went to the fantasy adventure film The Golden Compass.
More than a decade later, Johnson returned to the Oscars for his most recent appearance at the 96th Academy Awards in 2024.
This time, he attended both as a presenter and in support of his close friend and Jungle Cruise co-star Emily Blunt, who had been nominated for Best Supporting Actress for her performance in Oppenheimer.
For the evening, Johnson opted for a bold fashion statement, wearing a custom metallic silver-grey suit by Dolce & Gabbana featuring wide peak lapels and a burgundy-lined silk shirt left dramatically unbuttoned nearly to his midsection.
While walking the red carpet, Johnson also made headlines by revealing that production on the live-action adaptation of Moana would begin later in 2024.
During the ceremony, Johnson presented the award for Best Film Editing, which ultimately went to Oppenheimer.
He also shared a playful moment on stage with Bad Bunny, wishing the singer a happy 30th birthday as the audience applauded.
Although Johnson has become a global box-office powerhouse for more than a decade, he has yet to receive a nomination or win at the Academy Awards.
The actor, widely known as “The Rock,” attended the 80th ceremony as an invited presenter, marking a significant milestone in his growing film career.
For the occasion, Johnson wore a classic black tuxedo paired with a crisp white shirt and a traditional black bow tie, embracing the formal style expected at the high-profile event.
During the ceremony, Johnson presented the award for Best Visual Effects, which ultimately went to the fantasy adventure film The Golden Compass.
More than a decade later, Johnson returned to the Oscars for his most recent appearance at the 96th Academy Awards in 2024.
This time, he attended both as a presenter and in support of his close friend and Jungle Cruise co-star Emily Blunt, who had been nominated for Best Supporting Actress for her performance in Oppenheimer.
For the evening, Johnson opted for a bold fashion statement, wearing a custom metallic silver-grey suit by Dolce & Gabbana featuring wide peak lapels and a burgundy-lined silk shirt left dramatically unbuttoned nearly to his midsection.
While walking the red carpet, Johnson also made headlines by revealing that production on the live-action adaptation of Moana would begin later in 2024.
During the ceremony, Johnson presented the award for Best Film Editing, which ultimately went to Oppenheimer.
He also shared a playful moment on stage with Bad Bunny, wishing the singer a happy 30th birthday as the audience applauded.
Although Johnson has become a global box-office powerhouse for more than a decade, he has yet to receive a nomination or win at the Academy Awards.
6points
#13 Renée Zellweger, 1999 vs. 2021
Renée Zellweger made her Academy Awards debut in 1999 as an emerging Hollywood star following her breakout role in Jerry Maguire.
The actress attended the 71st ceremony as a presenter, wearing a mauve-colored, floor-length gown designed by L'Wren Scott.
The elegant dress featured a form-fitting silhouette with a gold-embroidered turtleneck neckline, along with a fringe hemline and a short train trailing behind her on the carpet.
During the ceremony, Renée introduced one of the nominees for Best Original Song, presenting the live performance of A Soft Place to Fall from the film The Horse Whisperer.
Over two decades later, Zellweger made her most recent Oscars appearance at the 93rd Academy Awards in 2021.
The ceremony was held at Union Station as part of the pandemic-era format, and Zellweger was part of a small, socially distanced group of A-list presenters.
Returning as the previous year’s Best Actress winner for her portrayal of Judy Garland in Judy, Zellweger attended the ceremony to present the award for Best Actor in a Leading Role.
For the occasion, she wore a custom vibrant pink tea-length gown from Giorgio Armani Privé featuring a strapless sweetheart neckline, a front leg slit, and a fitted bodice.
She completed the look with a chic shoulder-length bob hairstyle, which was a departure from her typical longer waves.
The actress presented the evening’s final award to Anthony Hopkins for his performance in The Father.
However, because Hopkins was not present at the ceremony, the moment created an awkward ending to the broadcast, which abruptly cut to the credits and left many viewers confused.
The actress attended the 71st ceremony as a presenter, wearing a mauve-colored, floor-length gown designed by L'Wren Scott.
The elegant dress featured a form-fitting silhouette with a gold-embroidered turtleneck neckline, along with a fringe hemline and a short train trailing behind her on the carpet.
During the ceremony, Renée introduced one of the nominees for Best Original Song, presenting the live performance of A Soft Place to Fall from the film The Horse Whisperer.
Over two decades later, Zellweger made her most recent Oscars appearance at the 93rd Academy Awards in 2021.
The ceremony was held at Union Station as part of the pandemic-era format, and Zellweger was part of a small, socially distanced group of A-list presenters.
Returning as the previous year’s Best Actress winner for her portrayal of Judy Garland in Judy, Zellweger attended the ceremony to present the award for Best Actor in a Leading Role.
For the occasion, she wore a custom vibrant pink tea-length gown from Giorgio Armani Privé featuring a strapless sweetheart neckline, a front leg slit, and a fitted bodice.
She completed the look with a chic shoulder-length bob hairstyle, which was a departure from her typical longer waves.
The actress presented the evening’s final award to Anthony Hopkins for his performance in The Father.
However, because Hopkins was not present at the ceremony, the moment created an awkward ending to the broadcast, which abruptly cut to the credits and left many viewers confused.
Report
6points
#14 Edward Norton, 1997 vs. 2025
When Edward Norton first stepped onto the Academy Awards red carpet in 1997, he was just 27 years old and attended the ceremony as a first-time nominee for Best Supporting Actor following his breakout film debut in Primal Fear.
Norton’s chilling performance as altar boy Aaron Stampler quickly made him one of the most talked-about newcomers in the industry.
Earlier that year, he had already won a Golden Globe Award for the role, further cementing his reputation as the “next big thing” in Hollywood.
For his Oscars debut, Norton opted for a classic black tuxedo paired with a white shirt and a black bow tie, embracing the event’s traditional formal dress code.
Despite the immense praise surrounding his performance, Norton ultimately lost the Best Supporting Actor award to Cuba Gooding Jr. for his role in Jerry Maguire.
Norton made his most recent Oscars appearance at the 97th Academy Awards in 2025.
This time, he again attended as a nominee for Best Supporting Actor for his portrayal of folk legend Pete Seeger in the Bob Dylan biopic A Complete Unknown.
For the occasion, the actor wore a custom black Dior tuxedo styled by longtime collaborator Leesa Evans, once again embracing a timeless red-carpet look.
He attended the ceremony alongside his wife, Shauna Robertson, as the film’s cast drew major attention throughout the evening.
The appearance marked Norton’s fourth Academy Award nomination and his first in more than a decade.
However, he ultimately lost the Best Supporting Actor award to Kieran Culkin for his performance in A Real Pain.
Despite earning four nominations across three different decades, Norton has yet to take home a competitive Oscar.
Norton’s chilling performance as altar boy Aaron Stampler quickly made him one of the most talked-about newcomers in the industry.
Earlier that year, he had already won a Golden Globe Award for the role, further cementing his reputation as the “next big thing” in Hollywood.
For his Oscars debut, Norton opted for a classic black tuxedo paired with a white shirt and a black bow tie, embracing the event’s traditional formal dress code.
Despite the immense praise surrounding his performance, Norton ultimately lost the Best Supporting Actor award to Cuba Gooding Jr. for his role in Jerry Maguire.
Norton made his most recent Oscars appearance at the 97th Academy Awards in 2025.
This time, he again attended as a nominee for Best Supporting Actor for his portrayal of folk legend Pete Seeger in the Bob Dylan biopic A Complete Unknown.
For the occasion, the actor wore a custom black Dior tuxedo styled by longtime collaborator Leesa Evans, once again embracing a timeless red-carpet look.
He attended the ceremony alongside his wife, Shauna Robertson, as the film’s cast drew major attention throughout the evening.
The appearance marked Norton’s fourth Academy Award nomination and his first in more than a decade.
However, he ultimately lost the Best Supporting Actor award to Kieran Culkin for his performance in A Real Pain.
Despite earning four nominations across three different decades, Norton has yet to take home a competitive Oscar.
5points
#15 Leonardo DiCaprio, 1994 vs. 2020
When Leonardo DiCaprio first stepped onto the red carpet at the Academy Awards in 1994, he was a 19-year-old rising star celebrating his first Oscar nomination for Best Supporting Actor for his critically acclaimed performance as Arnie Grape in What's Eating Gilbert Grape.
For his Oscars debut, DiCaprio wore a classic, slightly oversized black tuxedo paired with a white dress shirt and a traditional black bow tie.
The actor also wore a red ribbon pin on his tuxedo lapel to show support for AIDS awareness.
The pin was created in 1991 by the Visual AIDS Artists Caucus to raise awareness and demonstrate compassion at a time when the epidemic was devastating the arts community.
At the time, Leonardo was one of the youngest nominees in the category’s history.
He later admitted in interviews that he was actually terrified of winning the award because he feared having to deliver a speech in front of so many legendary figures in the film industry.
Although his performance earned widespread praise, DiCaprio ultimately lost the Best Supporting Actor award to Tommy Lee Jones for his role in The Fugitive.
DiCaprio’s last Oscar appearance came in 2020, when he attended as a nominee for Best Actor for his portrayal of fading television star Rick Dalton in Once Upon a Time in Hollywood.
For the occasion, the actor opted for a custom black tuxedo by Giorgio Armani, maintaining his signature classic red-carpet style with a traditional bow tie and fitted tailoring.
The evening also marked a notable personal milestone, as DiCaprio attended the ceremony with his then-girlfriend, Camila Morrone.
It was his first time bringing a partner to the Oscars in 15 years, since attending with Gisele Bündchen in 2005.
During the broadcast, DiCaprio also received a playful shoutout from his co-star Brad Pitt, who won Best Supporting Actor that evening.
In his acceptance speech, Pitt affectionately thanked the actor using his well-known nickname “LDC,” joking, “Leo, I’ll ride on your coattails any day, man. The view’s fantastic.”
DiCaprio did not win the Best Actor award that year; the honor ultimately went to Joaquin Phoenix for Joker.
For his Oscars debut, DiCaprio wore a classic, slightly oversized black tuxedo paired with a white dress shirt and a traditional black bow tie.
The actor also wore a red ribbon pin on his tuxedo lapel to show support for AIDS awareness.
The pin was created in 1991 by the Visual AIDS Artists Caucus to raise awareness and demonstrate compassion at a time when the epidemic was devastating the arts community.
At the time, Leonardo was one of the youngest nominees in the category’s history.
He later admitted in interviews that he was actually terrified of winning the award because he feared having to deliver a speech in front of so many legendary figures in the film industry.
Although his performance earned widespread praise, DiCaprio ultimately lost the Best Supporting Actor award to Tommy Lee Jones for his role in The Fugitive.
DiCaprio’s last Oscar appearance came in 2020, when he attended as a nominee for Best Actor for his portrayal of fading television star Rick Dalton in Once Upon a Time in Hollywood.
For the occasion, the actor opted for a custom black tuxedo by Giorgio Armani, maintaining his signature classic red-carpet style with a traditional bow tie and fitted tailoring.
The evening also marked a notable personal milestone, as DiCaprio attended the ceremony with his then-girlfriend, Camila Morrone.
It was his first time bringing a partner to the Oscars in 15 years, since attending with Gisele Bündchen in 2005.
During the broadcast, DiCaprio also received a playful shoutout from his co-star Brad Pitt, who won Best Supporting Actor that evening.
In his acceptance speech, Pitt affectionately thanked the actor using his well-known nickname “LDC,” joking, “Leo, I’ll ride on your coattails any day, man. The view’s fantastic.”
DiCaprio did not win the Best Actor award that year; the honor ultimately went to Joaquin Phoenix for Joker.
5points
#16 Matt Damon, 1998 vs. 2017
Matt Damon was a 27-year-old rising star celebrating the enormous success of his breakout film Good Will Hunting, which he both starred in and co-wrote, when he attended the Academy Awards in 1998.
Damon attended the 70th Academy Awards as a double nominee that evening, recognized for Best Actor while also earning a nomination for Best Original Screenplay alongside his longtime friend and collaborator, Ben Affleck.
For his Oscars debut, the actor wore a classic black tuxedo paired with a white dress shirt and a traditional black bow tie.
He arrived at the ceremony with Affleck as well as his mother, Nancy Carlsson-Paige, making the moment a memorable milestone early in his career.
The night turned historic when Damon and Affleck won the Oscar for Best Original Screenplay for Good Will Hunting.
Taking the stage together, the pair delivered an energetic acceptance speech, appearing visibly overwhelmed as they thanked nearly everyone who had supported them, including their families and co-star, Robin Williams.
Although Damon was also nominated for Best Actor that year, the award ultimately went to Jack Nicholson for his performance in As Good as It Gets.
Nearly two decades later, Damon made his most recent Oscars appearance at the 89th Academy Awards in 2017.
This time, he attended as a nominee for Best Picture as one of the producers of the acclaimed drama Manchester by the Sea.
For the occasion, Damon wore a classic navy-blue three-piece Versace suit and arrived alongside his wife, Luciana Barroso.
The ceremony also marked the height of Damon’s long-running comedic “feud” with host Jimmy Kimmel.
Throughout the night, Kimmel repeatedly poked fun at the actor, including joking in his opening monologue that Damon had passed on the lead role in Manchester by the Sea in order to star in The Great Wall instead.
Later in the broadcast, Damon and Affleck returned to the stage together to present the award for Best Original Screenplay.
However, the orchestra repeatedly began playing loud music whenever Damon tried to speak, allowing Kimmel to jokingly “play him off” from the podium while conducting the band from backstage.
Damon also witnessed one of the most infamous moments in Oscars history that evening when La La Land was mistakenly announced as Best Picture before the award was ultimately corrected and given to Moonlight.
Damon attended the 70th Academy Awards as a double nominee that evening, recognized for Best Actor while also earning a nomination for Best Original Screenplay alongside his longtime friend and collaborator, Ben Affleck.
For his Oscars debut, the actor wore a classic black tuxedo paired with a white dress shirt and a traditional black bow tie.
He arrived at the ceremony with Affleck as well as his mother, Nancy Carlsson-Paige, making the moment a memorable milestone early in his career.
The night turned historic when Damon and Affleck won the Oscar for Best Original Screenplay for Good Will Hunting.
Taking the stage together, the pair delivered an energetic acceptance speech, appearing visibly overwhelmed as they thanked nearly everyone who had supported them, including their families and co-star, Robin Williams.
Although Damon was also nominated for Best Actor that year, the award ultimately went to Jack Nicholson for his performance in As Good as It Gets.
Nearly two decades later, Damon made his most recent Oscars appearance at the 89th Academy Awards in 2017.
This time, he attended as a nominee for Best Picture as one of the producers of the acclaimed drama Manchester by the Sea.
For the occasion, Damon wore a classic navy-blue three-piece Versace suit and arrived alongside his wife, Luciana Barroso.
The ceremony also marked the height of Damon’s long-running comedic “feud” with host Jimmy Kimmel.
Throughout the night, Kimmel repeatedly poked fun at the actor, including joking in his opening monologue that Damon had passed on the lead role in Manchester by the Sea in order to star in The Great Wall instead.
Later in the broadcast, Damon and Affleck returned to the stage together to present the award for Best Original Screenplay.
However, the orchestra repeatedly began playing loud music whenever Damon tried to speak, allowing Kimmel to jokingly “play him off” from the podium while conducting the band from backstage.
Damon also witnessed one of the most infamous moments in Oscars history that evening when La La Land was mistakenly announced as Best Picture before the award was ultimately corrected and given to Moonlight.
4points
#17 Brad Pitt, 1992 vs. 2021
The red carpet at the Academy Awards in 1992 marked Brad Pitt’s first taste of intense Hollywood attention as a rising star attending the ceremony as the guest of his then-girlfriend, Juliette Lewis.
Lewis had been nominated for Best Supporting Actress for her performance in Cape Fear.
The couple attended the 64th Academy Awards during what would soon become a breakthrough period in Pitt’s career following his memorable role in the Oscar-nominated film Thelma & Louise, which had been released the previous year.
Although he did not present or receive any awards that evening, Pitt still made an impression with his fashion, wearing a traditional black tuxedo paired with a crisp white dress shirt.
Nearly three decades later, Pitt made his most recent Oscars appearance at the 93rd Academy Awards in 2021.
Returning as the previous year’s Best Supporting Actor winner for his performance in Once Upon a Time in Hollywood, he attended the ceremony to present the award for Best Supporting Actress.
The pandemic-era ceremony was held at Union Station, with only a limited number of celebrities attending in person to maintain the broadcast’s “live movie” atmosphere.
For the evening, Pitt wore a classic black tuxedo by Brioni, the luxury menswear label for which he served as a global ambassador that year.
However, it was his hairstyle that drew the most attention, as the actor debuted a low man bun that quickly went viral online.
He notably skipped the red carpet that evening and entered the ceremony midway through the broadcast before taking the stage to present the award.
He ultimately presented the Best Supporting Actress Oscar to Youn Yuh-jung for her acclaimed performance in Minari, a film produced by Pitt’s company, Plan B Entertainment.
The 73-year-old actress jokingly addressed him in a starstruck tone at the podium, saying, “Mr. Brad Pitt, finally. Nice to meet you. Where were you when we were filming?”
Lewis had been nominated for Best Supporting Actress for her performance in Cape Fear.
The couple attended the 64th Academy Awards during what would soon become a breakthrough period in Pitt’s career following his memorable role in the Oscar-nominated film Thelma & Louise, which had been released the previous year.
Although he did not present or receive any awards that evening, Pitt still made an impression with his fashion, wearing a traditional black tuxedo paired with a crisp white dress shirt.
Nearly three decades later, Pitt made his most recent Oscars appearance at the 93rd Academy Awards in 2021.
Returning as the previous year’s Best Supporting Actor winner for his performance in Once Upon a Time in Hollywood, he attended the ceremony to present the award for Best Supporting Actress.
The pandemic-era ceremony was held at Union Station, with only a limited number of celebrities attending in person to maintain the broadcast’s “live movie” atmosphere.
For the evening, Pitt wore a classic black tuxedo by Brioni, the luxury menswear label for which he served as a global ambassador that year.
However, it was his hairstyle that drew the most attention, as the actor debuted a low man bun that quickly went viral online.
He notably skipped the red carpet that evening and entered the ceremony midway through the broadcast before taking the stage to present the award.
He ultimately presented the Best Supporting Actress Oscar to Youn Yuh-jung for her acclaimed performance in Minari, a film produced by Pitt’s company, Plan B Entertainment.
The 73-year-old actress jokingly addressed him in a starstruck tone at the podium, saying, “Mr. Brad Pitt, finally. Nice to meet you. Where were you when we were filming?”
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