Fashion is ever-evolving, but certain celebrity style moments remind us that iconic looks never truly fade. From red carpet recreations to modern spins on vintage ensembles, these 10 stars reached into the past to resurrect legendary fashion statements. Some were celebrated for their stylish tributes, while others stirred controversy with their daring interpretations. Did they honor the originals—or fall flat? 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 country queen passing the torch in style.
At the ACM Honors, Ballerini didn’t just honor Twain—she fully stepped into her legacy, donning the exact floor-length, sequined turtleneck gown Twain wore while performing “Man! I Feel Like a Woman!” at the peak of her career. The gown, preserved in the Grammy Museum archives, became a centerpiece of a powerful fashion tribute.
It was a bold move, but one that paid off. Twain was all in, happily lending the legendary dress, while Ballerini teased the reveal with a cheeky nod to The Sisterhood of the Traveling Pants. Fans were quick to praise the heartfelt homage, applauding Ballerini’s stunning recreation of a truly unforgettable look.
#2 Sabrina Carpenter And Madonna
Sabrina Carpenter revived one of Madonna’s most iconic looks—stepping into the legendary Bob Mackie dress from the 1991 Oscars—and gave it her own modern twist.
At the 2024 MTV VMAs, Sabrina shimmered in the same sequined, strapless masterpiece that Madonna once wore at the height of her Material Girl era. From the sweetheart neckline to the diamond accessories and Old Hollywood waves, she leaned fully into vintage glamour.
But was it a true Madonna-level moment? That’s still up for debate.
Rather than a carbon copy, Sabrina offered a more refined, polished take on the look. While it lacked the provocative flair and rebellious energy that defined Madonna’s original appearance, it remained a visually striking tribute.
The reception was mixed. Some fans were dazzled, while others questioned the styling. “The dress is gorgeous,” one commenter wrote, “but I don’t get why her team keeps styling her to look older. You can do bangs without going full Madonna/Marilyn.” Another added, “It feels like they’re struggling to match her sexier image with her naturally youthful vibe.”
#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.”
