Some dresses make history. And when today’s stars decide to resurrect those legendary looks, comparisons are inevitable.
From paying homage to old Hollywood glam to channeling pop royalty, some celebrities manage to breathe new life into vintage masterpieces, while others remind us why some moments are best left in the past.
Below, we take a look at some of the hits and misses from stars who recreated iconic looks from the past and sparked controversy on social media.
#1 Kelsea Ballerini And Shania Twain
Kelsea Ballerini wearing the Shania Twain 1999 Grammys dress: now that’s country music royalty passing the torch, literally.
For the ACM Honors, Ballerini didn’t just honor Twain—she wore her legacy, slipping into the floor-length, long-sleeved, sequin-covered turtleneck gown straight from the Grammy Museum archives.
A bold move, considering Twain owned that dress while belting out “Man! I Feel Like a Woman!” at the peak of her career at the award show.
The moment was clearly sentimental, with Twain happily lending the dress and Ballerini teasing the reveal with a “Sisterhood of the traveling dress” nod. Ballerini got a lot of positive reviews for her recreation of the look.
For the ACM Honors, Ballerini didn’t just honor Twain—she wore her legacy, slipping into the floor-length, long-sleeved, sequin-covered turtleneck gown straight from the Grammy Museum archives.
A bold move, considering Twain owned that dress while belting out “Man! I Feel Like a Woman!” at the peak of her career at the award show.
The moment was clearly sentimental, with Twain happily lending the dress and Ballerini teasing the reveal with a “Sisterhood of the traveling dress” nod. Ballerini got a lot of positive reviews for her recreation of the look.
15points
#2 Sabrina Carpenter And Madonna
Sabrina Carpenter stepped into the Bob Mackie dress Madonna wore to the 1991 Oscars and owned the moment.
She arrived at the 2024 MTV VMAs dripping in sequins, the same sparkling strapless Mackie masterpiece Madonna rocked when she was at her peak. The sweetheart neckline, the diamonds, the Old Hollywood curls—Carpenter was clearly going for it.
But did she give us Material Girl levels of iconic? That’s another story.
Sabrina brought her own charm to the moment, giving a modern, glamorous interpretation rather than a direct recreation. It may not have carried the same rebellious energy as Madonna’s original, but it was undeniably a dazzling nod to an iconic fashion moment.
A user wondered, “This dress is gorgeous, but idk why she and her team insist on aging her up with these hairstyles and makeup looks. You can do bangs without going full Madonna/Marilyn.”
Another replied, “I think it's because her team is having a hard time balancing Sabrina's current aesthetic (which leans s-xier) with her youthful/baby face.”
She arrived at the 2024 MTV VMAs dripping in sequins, the same sparkling strapless Mackie masterpiece Madonna rocked when she was at her peak. The sweetheart neckline, the diamonds, the Old Hollywood curls—Carpenter was clearly going for it.
But did she give us Material Girl levels of iconic? That’s another story.
Sabrina brought her own charm to the moment, giving a modern, glamorous interpretation rather than a direct recreation. It may not have carried the same rebellious energy as Madonna’s original, but it was undeniably a dazzling nod to an iconic fashion moment.
A user wondered, “This dress is gorgeous, but idk why she and her team insist on aging her up with these hairstyles and makeup looks. You can do bangs without going full Madonna/Marilyn.”
Another replied, “I think it's because her team is having a hard time balancing Sabrina's current aesthetic (which leans s-xier) with her youthful/baby face.”
10points
#3 Kaia Gerber And Bianca Jagger
Kaia Gerber’s first-ever Met Gala look was a vintage throwback done right.
For her debut at fashion’s biggest night, she channeled the Bianca Jagger, specifically her 1981 Met Gala gown, originally designed by Dior. And let’s be honest, paying homage to Bianca is a choice; you don’t just wear the dress, you wear the attitude.
Gerber tapped Oscar de la Renta to recreate the strapless black gown with delicate floral detailing around the neckline, bringing a touch of timeless elegance to the 2021 red carpet. She even nailed the beauty reference, stepping out with perfectly sculpted Jagger-esque waves, courtesy of hairstylist Guido Palau.
Now, was it a moment? Absolutely. But did it carry the same effortless, untouchable cool that Bianca exuded in the ‘80s? That’s up for debate.
One Redditor said, “She looks beautiful, but she’s just not serving the way Bianca was. She lacks the charisma, I think. She’s gorgeous but doesn’t have the presence.”
Another added, “Bianca Jagger’s look and posture are so elegant and refined. She’s like nobility or a golden-age Hollywood star. Not many people carry themselves like that today.”
For her debut at fashion’s biggest night, she channeled the Bianca Jagger, specifically her 1981 Met Gala gown, originally designed by Dior. And let’s be honest, paying homage to Bianca is a choice; you don’t just wear the dress, you wear the attitude.
Gerber tapped Oscar de la Renta to recreate the strapless black gown with delicate floral detailing around the neckline, bringing a touch of timeless elegance to the 2021 red carpet. She even nailed the beauty reference, stepping out with perfectly sculpted Jagger-esque waves, courtesy of hairstylist Guido Palau.
Now, was it a moment? Absolutely. But did it carry the same effortless, untouchable cool that Bianca exuded in the ‘80s? That’s up for debate.
One Redditor said, “She looks beautiful, but she’s just not serving the way Bianca was. She lacks the charisma, I think. She’s gorgeous but doesn’t have the presence.”
Another added, “Bianca Jagger’s look and posture are so elegant and refined. She’s like nobility or a golden-age Hollywood star. Not many people carry themselves like that today.”
9points
#4 Sydney Sweeney And Angelina Jolie
Sydney Sweeney stepping into the Marc Bouwer gown that Angelina Jolie wore to the 2004 Oscars? A bold choice, and honestly, she delivered. Well, almost.
Two decades later, the Euphoria star brought new life to the iconic ivory dress with its plunging neckline, ruched waist, and dramatic cut-away back. The nod to red carpet history was clear, and the execution was polished yet personal.
Sydney Sweeney kept the styling faithful to Jolie’s original moment, down to the white sash and layered Messika necklaces, but gave it her own twist with a voluminous, Marilyn-esque bob, adding a touch of vintage energy.
But here’s the thing: while Jolie wore this dress with effortless ease, Sydney’s version felt just a bit too structured.
As one Redditor put it, “I think this is a perfect example of someone who’s dress is wearing them.” The look was stunning, but instead of embodying the dress, she seemed slightly overpowered by its legacy.
Two decades later, the Euphoria star brought new life to the iconic ivory dress with its plunging neckline, ruched waist, and dramatic cut-away back. The nod to red carpet history was clear, and the execution was polished yet personal.
Sydney Sweeney kept the styling faithful to Jolie’s original moment, down to the white sash and layered Messika necklaces, but gave it her own twist with a voluminous, Marilyn-esque bob, adding a touch of vintage energy.
But here’s the thing: while Jolie wore this dress with effortless ease, Sydney’s version felt just a bit too structured.
As one Redditor put it, “I think this is a perfect example of someone who’s dress is wearing them.” The look was stunning, but instead of embodying the dress, she seemed slightly overpowered by its legacy.
3points
#5 Halsey And Elizabeth Hurley
Halsey brought back the Elizabeth Hurley 1996 Versace gown for the 2024 MTV VMAs. Now, that’s how you pull a look straight from the archives.
This beaded silk chiffon masterpiece, originally designed by Gianni Versace, was famously worn by Hurley to the grand opening of Versace’s Fifth Avenue boutique. It hadn’t been touched in nearly 30 years, and Halsey made sure its comeback was worth the wait.
With Swarovski crystals catching every flash of the camera, they styled the look with drop chain-link earrings, burnished rings, and a moody taupe lip, a subtle nod to Hurley’s original glam. And this was a fashion resurrection.
Halsey called the dress a “miracle to find,” and considering the level of early Versace excellence on display, that’s no exaggeration.
Now, was it an exact Hurley replica? No. And that’s why it worked. Halsey didn’t try to outdo or mimic Hurley, but instead, they gave it a new energy—one that felt effortless, edgy, and right at home in 2024.
One Redditor commented on the revival fashion, saying, “Again… Sabrina, and now this. Fashion has hit its reboot era.”
Another replied, “But fashion has always had a reboot era. It’s literally vintage fashion. The difference is that we have access to a bazillion photographs of the OG look and contemporary celebrities at every waking moment, so it feels fatigued. Recycled fashion has always been recycled fashion.”
This beaded silk chiffon masterpiece, originally designed by Gianni Versace, was famously worn by Hurley to the grand opening of Versace’s Fifth Avenue boutique. It hadn’t been touched in nearly 30 years, and Halsey made sure its comeback was worth the wait.
With Swarovski crystals catching every flash of the camera, they styled the look with drop chain-link earrings, burnished rings, and a moody taupe lip, a subtle nod to Hurley’s original glam. And this was a fashion resurrection.
Halsey called the dress a “miracle to find,” and considering the level of early Versace excellence on display, that’s no exaggeration.
Now, was it an exact Hurley replica? No. And that’s why it worked. Halsey didn’t try to outdo or mimic Hurley, but instead, they gave it a new energy—one that felt effortless, edgy, and right at home in 2024.
One Redditor commented on the revival fashion, saying, “Again… Sabrina, and now this. Fashion has hit its reboot era.”
Another replied, “But fashion has always had a reboot era. It’s literally vintage fashion. The difference is that we have access to a bazillion photographs of the OG look and contemporary celebrities at every waking moment, so it feels fatigued. Recycled fashion has always been recycled fashion.”
0points
#6 Blake Lively And Britney Spears
Blake Lively in the very same Versace dress Britney Spears wore in 2002 felt like a pop culture crossover moment.
Attending the It Ends With Us premiere, Lively revived the Y2K classic, sequined, floral, and butterfly-adorned dress with all the nostalgia and sparkle one could ask for. And she knew the significance.
"It is Britney's actual dress," Lively told People. "It should be in the Smithsonian or the Met. But it's on me. I feel so lucky!"
The dress itself is pure early 2000s excess in the best way. Lively’s blonde waves gave effortless red carpet-meets-pop princess energy, making it clear this was a tribute, not just another vintage moment.
But in 2002, this look was part of Britney’s reigning era, a symbol of effortless, untouchable pop stardom. While Lively wears it beautifully, it received negative backlash from online users.
One user said, “It really just didn't fit her right. She shouldn't have tried so hard to make fetch happen.” Another mentioned Spears’s tumultuous life at the time, saying, “After all Britney has been through, it’s so incredibly tone-deaf of Blake.”
Attending the It Ends With Us premiere, Lively revived the Y2K classic, sequined, floral, and butterfly-adorned dress with all the nostalgia and sparkle one could ask for. And she knew the significance.
"It is Britney's actual dress," Lively told People. "It should be in the Smithsonian or the Met. But it's on me. I feel so lucky!"
The dress itself is pure early 2000s excess in the best way. Lively’s blonde waves gave effortless red carpet-meets-pop princess energy, making it clear this was a tribute, not just another vintage moment.
But in 2002, this look was part of Britney’s reigning era, a symbol of effortless, untouchable pop stardom. While Lively wears it beautifully, it received negative backlash from online users.
One user said, “It really just didn't fit her right. She shouldn't have tried so hard to make fetch happen.” Another mentioned Spears’s tumultuous life at the time, saying, “After all Britney has been through, it’s so incredibly tone-deaf of Blake.”
-1point
#7 Madison Beer And Beyoncé
Madison Beer wearing Beyoncé’s 2003 Dolce & Gabbana dress for the 2021 MTV VMAs was a moment, but let’s break it down.
The rose-pink silk, the corset detailing, the literal history of this piece: she had all the ingredients for a perfect throwback. But when you’re wearing something Beyoncé already made iconic, you better bring something fresh to the table.
Beer tweaked the styling, leaving the lace-up slit undone to the hip instead of stopping at the knee like Bey did on The Late Show with David Letterman.
The result? A sultrier, more modern take, paired with metallic heels instead of Beyoncé’s sparkly pink peep-toes. Both rocked soft waves and a pink lip, proving some details are too good to change.
But Beyoncé was this dress in 2003. She had that early-’00s pop star dominance, that effortless confidence that turned a simple D&G gown into a legendary moment.
Madison looked gorgeous, but when you step into Queen Bey’s fashion legacy, the comparisons are inevitable.
One user lashed out at Beer, saying, “Some mediocre white girl industry plant wore a dress by a talented black woman who is considered the most outstanding female entertainer of all time. Life is strange.”
The rose-pink silk, the corset detailing, the literal history of this piece: she had all the ingredients for a perfect throwback. But when you’re wearing something Beyoncé already made iconic, you better bring something fresh to the table.
Beer tweaked the styling, leaving the lace-up slit undone to the hip instead of stopping at the knee like Bey did on The Late Show with David Letterman.
The result? A sultrier, more modern take, paired with metallic heels instead of Beyoncé’s sparkly pink peep-toes. Both rocked soft waves and a pink lip, proving some details are too good to change.
But Beyoncé was this dress in 2003. She had that early-’00s pop star dominance, that effortless confidence that turned a simple D&G gown into a legendary moment.
Madison looked gorgeous, but when you step into Queen Bey’s fashion legacy, the comparisons are inevitable.
One user lashed out at Beer, saying, “Some mediocre white girl industry plant wore a dress by a talented black woman who is considered the most outstanding female entertainer of all time. Life is strange.”
-3points
#8 Kylie Jenner And Marilyn Monroe
Let’s dive into Kylie Jenner's 2019 Halloween look, where she channeled Marilyn Monroe's iconic "Diamonds Are a Girl's Best Friend" ensemble from Gentlemen Prefer Blondes.
Kylie stepped out in a replica hot pink gown, an ode to Monroe’s legendary dress. The attempt was to capture that same rich, cinematic charm. Kylie's version truly sparkled under the lights, yes, but it was a tough act to follow.
Some fans felt that while the gown was glamorous, it missed the mark in embodying the magnetic charm and presence that Monroe radiated in every frame—while others were left speechless over the whole look.
Her fans loved Kylie's look. One said, “She’s amazing.” Another added, “Icon moment."
One user took a swing at Kim's Marilyn Monroe dress incident, saying, “This is how you respectfully channel an icon without trying to attach your name to her as well as not ruining a valuable piece of American history (JFK bday dress). Kim should take notes from Kylie.”
Kylie stepped out in a replica hot pink gown, an ode to Monroe’s legendary dress. The attempt was to capture that same rich, cinematic charm. Kylie's version truly sparkled under the lights, yes, but it was a tough act to follow.
Some fans felt that while the gown was glamorous, it missed the mark in embodying the magnetic charm and presence that Monroe radiated in every frame—while others were left speechless over the whole look.
Her fans loved Kylie's look. One said, “She’s amazing.” Another added, “Icon moment."
One user took a swing at Kim's Marilyn Monroe dress incident, saying, “This is how you respectfully channel an icon without trying to attach your name to her as well as not ruining a valuable piece of American history (JFK bday dress). Kim should take notes from Kylie.”
Report
-19points
#9 Ivanka Trump And Audrey Hepburn
Ivanka decided to channel the legendary Audrey Hepburn with a gown inspired by Audrey’s classic look from the 1954 film Sabrina in the 2025 Inaugural Ball, and the choice was anything but uncontroversial.
The gown itself, crafted by Givenchy, was aiming for that timeless Hepburn elegance but ended up sparking quite the debate.
Critics were quick to shade the details, calling the embroidery and texture “cartoonish” and far from the finesse of the original. And the drama didn’t stop at the fashion.
The audacity to evoke Audrey’s legacy on such a politically charged day set the internet on fire. People were not holding back, with some saying Audrey herself would have thrown a major side-eye at the Trumps for this bold fashion move.
It turned into a full-blown style scandal, with opinions flying left and right about appropriating an icon’s look in a context that couldn't be more mismatched.
One user simply said, “Hepburn would be insulted.” Among those who reacted to Ivanka’s look was Hepburn’s son, who commented on her mother’s style, adding, “Over the past 71 years, her legacy has grown to become transgenerational and transnational.”
The gown itself, crafted by Givenchy, was aiming for that timeless Hepburn elegance but ended up sparking quite the debate.
Critics were quick to shade the details, calling the embroidery and texture “cartoonish” and far from the finesse of the original. And the drama didn’t stop at the fashion.
The audacity to evoke Audrey’s legacy on such a politically charged day set the internet on fire. People were not holding back, with some saying Audrey herself would have thrown a major side-eye at the Trumps for this bold fashion move.
It turned into a full-blown style scandal, with opinions flying left and right about appropriating an icon’s look in a context that couldn't be more mismatched.
One user simply said, “Hepburn would be insulted.” Among those who reacted to Ivanka’s look was Hepburn’s son, who commented on her mother’s style, adding, “Over the past 71 years, her legacy has grown to become transgenerational and transnational.”
-33points
#10 Kim Kardashian And Marilyn Monroe
Yes, the very gown that Monroe wore back in 1962 to serenade President John F. Kennedy.
Getting into that historic garment was a feat in itself. Kim had to go through a major body transformation just to fit into it.
However, critics were quick to point out that while Kim did manage to squeeze into the gown, it just didn't sit right. Some said the fit was off, and it lacked that certain je ne sais quoi that Marilyn radiated.
And let's not overlook the concerns about the safety of this iconic piece of fashion history. The idea that this priceless outfit could be damaged had historians and fashionistas alike clutching their pearls in horror!
The attempt sadly missed capturing the effortless charisma and the sparkling magic that Marilyn Monroe brought into the room. Kim did her best, but some shoes—or, in this case, some dresses—are just too legendary to fill.
One Redditor commented on Kim’s style choice, calling her “a woman who has had extensive plastic surgery to every part of her body went on a starvation diet to squeeze into A dress that Marilyn Monroe herself had to be sewn into.”
“As a result, the dress is pretty damaged. fabric (which is no longer sold since it's very flammable) is now stretched, nearly torn near the zipper. Many stones are now missing, and it's actually pretty sad,” they added.
Getting into that historic garment was a feat in itself. Kim had to go through a major body transformation just to fit into it.
However, critics were quick to point out that while Kim did manage to squeeze into the gown, it just didn't sit right. Some said the fit was off, and it lacked that certain je ne sais quoi that Marilyn radiated.
And let's not overlook the concerns about the safety of this iconic piece of fashion history. The idea that this priceless outfit could be damaged had historians and fashionistas alike clutching their pearls in horror!
The attempt sadly missed capturing the effortless charisma and the sparkling magic that Marilyn Monroe brought into the room. Kim did her best, but some shoes—or, in this case, some dresses—are just too legendary to fill.
One Redditor commented on Kim’s style choice, calling her “a woman who has had extensive plastic surgery to every part of her body went on a starvation diet to squeeze into A dress that Marilyn Monroe herself had to be sewn into.”
“As a result, the dress is pretty damaged. fabric (which is no longer sold since it's very flammable) is now stretched, nearly torn near the zipper. Many stones are now missing, and it's actually pretty sad,” they added.
-33points