10 Celebrity Outfit Throwbacks That Sparked Praise and Controversy
Fashion is always evolving, but some celebrity style moments prove that iconic looks never truly go out of style. From red carpet recreations to modern twists on vintage outfits, these 10 stars took inspiration from the past and brought legendary fashion moments back to life. While some earned praise for their stunning tributes, others sparked controversy with their bold choices. Did they do justice to the originals, or did they miss the mark? Let’s take a closer look at these unforgettable outfit throwbacks.
#1 Kelsea Ballerini And Shania Twain
Kelsea Ballerini wearing Shania Twain’s iconic 1999 Grammys dress—now that’s a true country music queen passing the torch.
For the ACM Honors, Ballerini didn’t just pay tribute to Twain; she embodied her legacy, stepping into the exact floor-length, sequined turtleneck gown straight from the Grammy Museum archives.
It was a bold choice, considering Twain originally rocked the dress while performing “Man! I Feel Like a Woman!” at the height of her career.
The moment was clearly meaningful, with Twain happily lending the dress and Ballerini teasing the reveal with a playful “Sisterhood of the Traveling Dress” reference. Fans loved the tribute, praising Ballerini for her stunning recreation.
#2 Sabrina Carpenter And Madonna
Sabrina Carpenter stepped into the iconic Bob Mackie dress Madonna wore to the 1991 Oscars—and she made it her own.
At the 2024 MTV VMAs, she dazzled in the same sequined, strapless Mackie masterpiece that Madonna once rocked at the height of her career. From the sweetheart neckline to the diamond accessories and Old Hollywood curls, Sabrina fully embraced the vintage glam.
But did she deliver a Material Girl-level moment? That’s up for debate.
Rather than a direct recreation, Sabrina put a modern, polished spin on the look. While it didn’t carry the same rebellious edge as Madonna’s original, it was still a stunning tribute to an unforgettable fashion moment.
Some fans, however, had mixed feelings. One commented, “This dress is gorgeous, but I don’t get why her team keeps styling her to look older with these hair and makeup choices. You can do bangs without going full Madonna/Marilyn.”
Another added, “I think they’re struggling to balance her current aesthetic, which leans sexier, with her naturally youthful face.”
#3 Kaia Gerber And Bianca Jagger
Kaia Gerber’s Met Gala debut was a masterclass in vintage-inspired elegance.
For her first appearance at fashion’s biggest night, she paid homage to Bianca Jagger, channeling the legendary socialite’s 1981 Met Gala look originally designed by Dior. And let’s be real—honoring Bianca isn’t just about the dress, it’s about the attitude.
Gerber enlisted Oscar de la Renta to recreate the strapless black gown, complete with delicate floral detailing along the neckline, exuding timeless sophistication. She even nailed the beauty reference, stepping onto the 2021 red carpet with sculpted, Jagger-esque waves styled by Guido Palau.
But did it capture the effortless, untouchable cool of Bianca in the ‘80s? That’s where opinions differ.
One Redditor commented, “She looks stunning, but she’s not serving the way Bianca did. She’s beautiful but lacks the same charisma and presence.”
Another added, “Bianca Jagger had this regal elegance, like old Hollywood royalty. That kind of aura is rare today.”
#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 for the most part, she delivered.
Two decades later, the Euphoria star revived the iconic ivory dress, complete with its plunging neckline, ruched waist, and dramatic cut-away back. The tribute to red carpet history was undeniable, and her execution was both polished and personal.
She stayed true to Jolie’s original styling, keeping the white sash and layered Messika necklaces, but added her own twist with a voluminous, Marilyn-inspired bob, injecting a touch of vintage glamour.
But here’s the thing: while Jolie wore the dress with effortless confidence, Sydney’s version felt just a bit too structured.
As one Redditor put it, “This is a perfect example of someone being worn by the dress rather than owning it.” The look was undeniably stunning, but instead of fully embodying the moment, she seemed slightly overshadowed by its legacy.
#5 Blake Lively And Britney Spears
Blake Lively stepping into the exact Versace dress Britney Spears wore in 2002 felt like a pop culture crossover for the ages.
At the It Ends With Us premiere, Lively revived the Y2K classic—sequined, floral, and butterfly-adorned—bringing back all the nostalgia and sparkle. And she knew exactly how iconic the moment was.
“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 peak early 2000s excess in the best way, and Lively’s signature blonde waves added a red carpet-meets-pop princess vibe. It was clear this wasn’t just another vintage throwback—it was a tribute.
But in 2002, Britney was at the height of her pop superstardom, making the look feel effortless and untouchable. While Lively wore it beautifully, the reception online was mixed.
One user commented, “It just didn’t fit her right. She shouldn’t have tried so hard to make fetch happen.”
Another pointed to Spears’s struggles over the years, saying, “After everything Britney has been through, this feels incredibly tone-deaf of Blake.”
#6 Halsey and Elizabeth Hurley
Halsey revived Elizabeth Hurley’s iconic 1996 Versace gown for the 2024 MTV VMAs, and that’s how you pull a look straight from the archives.
Originally designed by Gianni Versace, this beaded silk chiffon masterpiece made history when Hurley first wore it to the grand opening of Versace’s Fifth Avenue boutique. Untouched for nearly 30 years, its return was well worth the wait.
With Swarovski crystals shimmering under the camera flashes, Halsey styled the gown with chain-link drop earrings, burnished rings, and a moody taupe lip, a subtle nod to Hurley’s original glam. The result was a true fashion resurrection.
Calling the dress a “miracle to find,” Halsey wasn’t exaggerating. Early Versace excellence at this level is rare, and they made it their own.
Was it an exact Hurley replica? No, and that’s exactly why it worked. Instead of mimicking the past, Halsey infused the look with a fresh, effortless edge that felt right at home in 2024.
One Redditor summed it up best: “Again… Sabrina, and now this. Fashion has hit its reboot era.”
Another replied, “But fashion has always been a reboot era. It’s literally vintage fashion. The difference is, we now have a bazillion photographs of the OG look and contemporary celebrities at every waking moment, so it feels fatigued.”
#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 need to bring something fresh to the table.
Beer tweaked the styling by leaving the lace-up slit undone to the hip instead of stopping at the knee, as Beyoncé did on The Late Show with David Letterman.
The result was 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 in 2003, Beyoncé was this dress. She had that early-2000s pop star dominance and 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 put it bluntly: “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.”
#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 of Monroe’s legendary hot pink gown, aiming to capture that same rich, cinematic charm. Her version sparkled under the lights, but it was a tough act to follow.
Some fans felt that while the gown was undeniably glamorous, it lacked the magnetic presence Monroe exuded in every frame. Others, however, were left speechless by the overall look.
Her supporters praised the homage, with one commenting, “She’s amazing,” and another calling it an “icon moment.”
One user couldn’t resist comparing it to Kim Kardashian’s controversial Marilyn moment, saying, “This is how you respectfully channel an icon without trying to attach your name to her—or ruining a valuable piece of American history. Kim should take notes from Kylie.”
#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 at the 2025 Inaugural Ball, and the choice was anything but uncontroversial.
The gown, crafted by Givenchy, aimed for that timeless Hepburn elegance but ended up sparking quite the debate.
Critics were quick to criticize the details, calling the embroidery and texture “cartoonish” and far from the finesse of the original. The drama, however, extended beyond just fashion.
The decision to evoke Audrey’s legacy on such a politically charged day ignited a firestorm online. People did not hold back, with some saying Audrey herself would have given the Trumps a major side-eye for this bold fashion move.
What began as a style statement turned into a full-blown scandal, with opinions clashing over the appropriateness of borrowing an icon’s look in such a mismatched context.
One user simply stated, “Hepburn would be insulted.” Among those who reacted to Ivanka’s look was Hepburn’s son, who commented on his mother’s enduring influence, saying, “Over the past 71 years, her legacy has grown to become transgenerational and transnational.”
#10 Kim Kardashian and Marilyn Monroe
Kim Kardashian’s attempt to channel Marilyn Monroe in the iconic 1962 gown, worn by Monroe while serenading President John F. Kennedy, sparked plenty of conversation.
Fitting into the historic dress was no easy feat. Kim underwent a significant body transformation just to make it work. However, critics were quick to note that while she managed to squeeze into the gown, it did not quite sit right. Some felt the fit was off and lacked the effortless allure that Marilyn naturally exuded.
Beyond aesthetics, concerns arose over the preservation of this irreplaceable piece of fashion history. The thought of potential damage left historians and fashion enthusiasts horrified.
Despite Kim’s best efforts, the magic Monroe carried simply could not be replicated. Some legacies and dresses are just too legendary to recreate.
One Redditor summed up the controversy, stating, “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.”
They went on to add, “As a result, the dress is pretty damaged. The fabric, which is no longer produced due to its flammability, is now stretched and nearly torn near the zipper. Many stones are missing, and it is actually pretty sad.”