Fashion has always had a way of revisiting the past, especially when it comes to celebrities who love to pay homage to iconic looks. Whether it’s a legendary red carpet gown or a performance outfit that became a cultural moment, fashion reboots are a way for today’s stars to resurrect these timeless styles. But, just like in any trend, some tributes land perfectly, while others fall short.
In this article, we’ll take a closer look at 10 celebrity fashion reboots that have left us with mixed feelings—whether they’ve been hits, misses, or somewhere in between. From Grammy-worthy gowns to Met Gala masterpieces, we’ll explore the highs and lows of these fashion tributes. Were these moments as iconic as their originals, or did they miss the mark? Let’s dive into some of the most memorable celebrity fashion reboots of all time.
1. Kelsea Ballerini and Shania Twain: Passing the Torch with a Legendary Dress
Few dresses are as iconic in country music history as the one Shania Twain wore to the 1999 Grammys—a floor-length, long-sleeved, sequin-covered turtleneck gown. Twain, who was at the peak of her career, wore it during her performance of “Man! I Feel Like a Woman!” and solidified her place as a music and fashion icon.
Fast forward to the 2021 ACM Honors, where Kelsea Ballerini, one of today’s rising country stars, honored Twain by wearing the same gown—one that had been preserved in the Grammy Museum archives. The decision to wear this iconic piece was a bold one, especially given the stature of Twain’s original moment. The emotional gesture was well-received, with Twain herself lending the dress to Ballerini, and Ballerini even teasing a “Sisterhood of the Traveling Dress” reference.
While the tribute was seen as a beautiful passing of the torch, the reactions from fans and critics were mixed. Many praised Ballerini for respecting the legacy of Twain and giving the dress new life, while others wondered if she was overshadowed by the original magic of the moment. Ultimately, Ballerini’s reboot became a touching homage, and most agreed it was a success—albeit with a hint of nostalgia.
Check out the video as Shania Twain reacts to Kelsea Ballerini wearing her dress – a moment you don’t want to miss!
2. Sabrina Carpenter and Madonna: A Sequin Masterpiece with a Modern Twist
Madonna’s fashion choices have always been at the forefront of pop culture, from her early 1980s “Material Girl” look to her more daring outfits throughout her career. One of her most memorable fashion moments came in 1991 when she wore a stunning Bob Mackie dress to the Oscars. The sparkling silver gown, with its sweetheart neckline and diamonds, became an instant icon, reflecting Madonna’s powerful stage presence and her status as pop royalty.
Fast forward to 2024, when Sabrina Carpenter, the rising star from Girl Meets World and Euphoria, paid homage to Madonna by donning the same Bob Mackie dress at the MTV VMAs. Carpenter’s interpretation of the gown was undeniably glamorous, with sequins catching the light and vintage Hollywood curls framing her face. However, the reception to her rendition was mixed. While some appreciated her updated take on the look, others felt that it lacked the raw, rebellious energy that Madonna had embodied in the original. Sabrina brought her own charm to the moment, but it didn’t carry the same level of iconic energy as Madonna’s version.
Despite the critiques, Carpenter’s modern spin on the gown showed that she could carry off the glamour, even if she didn’t quite capture the same aura as Madonna in the 90s. The dress was a dazzling nod to an unforgettable fashion moment, even if it didn’t quite replicate the magic.
Watch the video as Sabrina Carpenter and Madonna rock the same dress – who wore it better?
3. Kaia Gerber and Bianca Jagger: Paying Homage to Met Gala Elegance
Kaia Gerber, one of the top models of her generation, made her Met Gala debut in 2021, and she chose a bold way to make her entrance: by channeling the iconic look of Bianca Jagger, who wore a vintage Dior gown to the 1981 Met Gala. Bianca’s original gown, which featured delicate floral detailing around the neckline and a strapless silhouette, exuded elegance and effortless cool—traits that Jagger herself was known for.
Gerber’s homage to the look was executed flawlessly. She tapped Oscar de la Renta to recreate the gown, keeping the same timeless elegance while bringing a modern sensibility to the look. She nailed the beauty reference with sculpted waves, capturing the essence of Jagger’s Met Gala appearance. However, while Gerber looked stunning, some critics felt she lacked the same aura of unapproachable elegance that Bianca Jagger radiated in the 80s.
Many fans and fashion experts admired Gerber for attempting to channel one of the most iconic Met Gala looks in history, but the consensus was clear: while she looked beautiful, she didn’t quite capture the same magnetic charisma that made Jagger’s original moment so unforgettable.
4. Sydney Sweeney and Angelina Jolie: A Red Carpet Reboot That Missed the Mark
Sydney Sweeney, the breakout star from Euphoria, is no stranger to the red carpet. In 2021, she recreated one of Angelina Jolie’s most iconic looks, the Marc Bouwer gown Jolie wore to the 2004 Oscars. The dress, with its plunging neckline and ruched waist, was a statement of elegance and sensuality, and it became a moment in red carpet history.
When Sweeney wore the gown to the 2021 Vanity Fair Oscars afterparty, she kept many of the original styling cues, including the white sash and layered necklaces, but added her own twist with a voluminous Marilyn Monroe-inspired bob. While Sweeney’s version of the gown was undeniably beautiful, it didn’t quite carry the same effortless ease that Jolie had exuded when she wore it. Critics noted that while the dress looked stunning on Sweeney, it seemed as though the gown was wearing her, rather than the other way around.
In the end, Sweeney’s recreation of Jolie’s moment was a beautiful attempt, but it didn’t quite match the effortless grace and confidence of the original.
5 Halsey and Elizabeth Hurley: A Versace Revival with a Modern Edge
In 1996, Elizabeth Hurley became an instant fashion icon when she wore a beaded Versace gown to the grand opening of Versace’s Fifth Avenue boutique. The gown, adorned with Swarovski crystals, was a showstopper that solidified Hurley’s status as a fashion icon. Years later, in 2024, Halsey brought the dress back into the spotlight when she wore it to the MTV VMAs.
Halsey’s version of the dress was a stunning tribute to the original, with its intricate beading and bold statement-making silhouette. However, Halsey’s interpretation added a modern twist, making it clear that the revival was more than just a rehashing of Hurley’s iconic look. Halsey gave the dress new energy by pairing it with a moody taupe lip and edgier styling, which made the dress feel fresh while still honoring its origins.
While the look was undeniably glamorous, some critics noted that it wasn’t an exact replica of Hurley’s 1996 moment. But that’s what made Halsey’s version work—it was a perfect blend of nostalgia and contemporary fashion, showing how a classic piece could evolve while still retaining its magic.
6 Blake Lively and Britney Spears: The Y2K Dress That Sparked Pop Culture Nostalgia
Blake Lively’s tribute to Britney Spears’ 2002 Versace dress felt like a pop culture crossover moment. The dress, which Britney wore in the early 2000s, was a perfect embodiment of Y2K fashion, with its sequins, floral designs, and butterfly motifs.
Attending the It Ends With Us premiere, Lively revived this classic dress, knowing full well the significance of it. She even mentioned how lucky she felt to wear the same dress that Britney once wore. While Lively wore the dress beautifully, many fans and critics pointed out that the nostalgia around the moment overshadowed her rendition. The comparisons were inevitable, and many felt that while Lively looked stunning, the dress didn’t hold the same impact that it had in 2002 when it was part of Britney’s reign.
Lively’s attempt was a nod to one of pop culture’s most iconic moments, but it left some fans wondering if the dress was too tied to Britney’s persona for anyone else to wear it quite as effortlessly.
7. Madison Beer and Beyoncé: A Corset Dress and the Weight of Iconic Legacy
Madison Beer made waves at the 2021 MTV VMAs by wearing the same Dolce & Gabbana dress that Beyoncé wore in 2003. The dress was a masterpiece with rose-pink silk and corset detailing, but as we know with fashion, some pieces become legendary when worn by the right person. Beyoncé’s original moment was pure pop star dominance, effortlessly exuding confidence and allure.
Madison Beer’s take on the dress was a sultrier, more modern interpretation. While she added a twist with an undone slit and metallic heels, it didn’t quite match the commanding presence that Beyoncé had brought to the look. The comparisons were inevitable, and while Beer looked stunning, the legacy of Beyoncé in that dress was hard to shake. Some fans even called Beer’s attempt a “miss” because the dress felt more like a trend than an iconic moment.
8. Kylie Jenner and Marilyn Monroe: The Pink Gown That Divided Fans
In 2019, Kylie Jenner decided to channel Marilyn Monroe for Halloween, recreating the iconic pink gown Monroe wore for Diamonds Are a Girl’s Best Friend in Gentlemen Prefer Blondes. While Jenner’s version sparkled under the lights, it didn’t quite capture the charm and presence that Monroe exuded when she wore it.
The gown, which was replicated to near perfection, failed to deliver the same magnetic effect that Monroe’s original moment had. Fans were split on whether Jenner’s tribute did justice to Monroe’s legacy, with some praising her for the effort and others criticizing her for missing the mark in terms of Monroe’s natural charisma.
Watch the video comparing Kylie Jenner’s 20s style to Marilyn Monroe’s iconic 50s dress – who nailed the look?
9. Ivanka Trump and Audrey Hepburn: A Controversial Fashion Moment
Ivanka Trump’s decision to channel Audrey Hepburn’s 1954 Sabrina gown for the 2025 Inaugural Ball created a massive stir. The Givenchy gown was supposed to embody Hepburn’s timeless elegance, but the execution fell short. Critics were quick to point out the “cartoonish” embroidery and texture of the gown, which they felt lacked the refinement of the original.
What truly sparked outrage, however, was the political context in which Ivanka wore the dress. Many felt that invoking Audrey Hepburn’s legacy during such a politically charged day was tone-deaf, with some even claiming that Hepburn herself would have objected to this tribute.
10. Kim Kardashian and Marilyn Monroe: The Dress That Sparked Outrage
Kim Kardashian’s attempt to wear the iconic 1962 gown Marilyn Monroe wore to serenade President John F. Kennedy became one of the most controversial fashion moments in recent history. The dress, which was a priceless piece of fashion history, was damaged in the process, leading to outrage from fashion historians and fans alike.
While Kardashian’s body transformation to fit into the dress was widely discussed, the damage to the iconic piece and the comparisons to Monroe’s effortless glamour overshadowed the moment. Critics argued that some dresses are just too legendary to be worn by others without losing their magic.
Final Thoughts: Fashion Reboots – A Double-Edged Sword of Nostalgia and Controversy
Celebrity fashion reboots are a fascinating way for stars to honor the icons of the past while making their own mark on the fashion world. While some reboots are met with widespread praise, others reveal how difficult it is to truly capture the essence of a legendary look. The key to a successful fashion reboot lies in balancing respect for the original moment with a fresh interpretation that resonates with today’s audience.
Ultimately, these reboots are a reminder that fashion is not just about the clothes we wear—it’s about the moments they create and the stories they tell. Whether they succeed or fail, celebrity fashion reboots keep the conversation about style alive, proving that the past and present can coexist in the ever-evolving world of fashion.
As more celebrities continue to revisit iconic looks from the past, we can only imagine what other unforgettable moments await on the red carpet, blending nostalgia with innovation in a never-ending cycle of fashion evolution.
