Ever spot a celebrity in a jaw-dropping outfit and realize you’ve seen it before? When stars wear the same dress or suit, it sparks a delicious debate about who wore it best. These fashion face-offs are a love letter to style, showcasing how unique personalities breathe new life into iconic designs.
From retro comebacks to serendipitous twinning on the same red carpet, these are moments of sheer enchantment. In 2025, celebrity style continues to fascinate us with equal degrees of nostalgia and fresh panache. Here are 14 unforgettable instances of twinning between stars in fashion brilliance.
This isn’t winner-picking it’s a toast to the endless fashion wheel. Grab a front-row seat as we dissect these iconic looks, from Hollywood royalty to pop princesses. Here’s to the gowns, suits, and stories that still have us buzzing!
1. Selena Gomez & Natalie Portman in Vintage Mugler
Selena Gomez and Natalie Portman exchanged glances in the same black velvet Mugler dress, a vintage find that screams ageless elegance. Portman wore it for the first time at the 2021 L.A. Dance Project Gala, her understated elegance giving the dress room to shine. Its intricate make-up was the perfect combination for her classic style.
Skip ahead to 2025, and Gomez wore the same dress on The Tonight Show, updating it with edge. Her fearless styling read: statement accessories or a sleek blowout transformed the look into something uniquely her own. It’s evidence that Mugler’s creations are still showstoppers decades later.
- Timeless Appeal: The cut and velvet of the gown transcend time.
- Star Power: Both women brought the dress to life through their charm.
- Styling Twist: Gomez’s updated version differed from Portman’s understatement.
This face-off is a celebration of the eternal beauty of fashion. Both actresses brought their own persona to the dress, and it looked both new and old. Who wore it best? You decide!
2. Keke Palmer & Jamie Lee Curtis in 1985 Chanel
Picture a black and gold 1985 Chanel ensemble, radiating retro cool. Jamie Lee Curtis first sported it to the American Cinematheque Awards, radiating ’80s glamour with unrepentant audacity. The look was all Chanel impeccable, but dangerously flashy.
Years later, Keke Palmer revived this retro look in 2025, retaining it’s vivacity and freshness. Her youthfulness and playfulness injected the outfit with a new makeover. Palmer’s capability to reinvent the classics was clear.
- Vintage Chic: Chanel’s design effortlessly traverses decades.
- Bold Vibes: Curtis’s ’80s look clashed with Palmer’s cool.
- Fashion Legacy: The outfit demonstrates that fashion never gets outdated.
This showdown spans two decades with Chanel’s brilliance. Every woman honored the design legacy while putting their own stamp on it. It reminds us that great fashion is a story across generations.
3. Taylor Swift & Malia Obama in Vivienne Westwood Plaid
Who knew a plaid Vivienne Westwood shirt would generate that kind of buzz? Pop culture icon Taylor Swift, queen of the genre, wore it with effortless laid-back chic, just right for her 2025 vibe. Readers immediately picked up the look, setting off social media buzz.
The déjà vu was of Malia Obama, who also sported the same shirt at the 2024 Deauville Film Festival. Her low-key intellectual style brought the plaid fresh, easy. It is remarkable the way something casual was turned into a statement.
Westwood’s design shows the scope of fashion. Swift’s accessible cool and Obama’s introvert confidence proved its utility. This twinning twist of surprise is a heartwarming homage to shared style between worlds.
4. Simone Ashley & Jess Hunt in Jacquemus
What a red-carpet twist of fate! Simone Ashley and Jess Hunt rocked the 2024 Glamour Women of the Year Awards in the same cream Jacquemus dress. Its dramatic open-back design shouted modern glamour, perfect for both actresses.
Ashley, the Bridgerton star, brought sultry sophistication to the table, and Hunt, the beauty mogul, brought a chic businesswoman’s edge. Intricate styling tweaks like accessories or hair gave each look a special touch. It was a stunning overlap that lit up the occasion.
This rare same-event twinny did 2025’s fashion scene a double take. The striking shape of the dress benefited both women’s bold attitudes. It’s proof of Jacquemus’s talent for creating pieces that are universally coveted.
5. Halsey & Elizabeth Hurley in Vintage Versace
We went back in time to the ’90s at the 2024 VMAs with Halsey stepping out in a retro Versace gown first modeled by Elizabeth Hurley in 1996. Hurley’s first-time visit to a Versace boutique opening was ’90s chic at its finest adventurous and provocative. The gown was stun-worthy then and now.
Halsey’s punk-tinged, modern update brought the gown into 2025 with fierce enthusiasm. She updated it as a nod to Hurley’s legendary moment in a way that kept it relevant. It is a love note to Versace’s timeless charm.
- 90s Flashback: Hurley’s aesthetic embodied the graphic style of an era.
- Contemporary Reboot: Halsey’s refresh maintained the dress’s relevance.
- Timeless Genius: Versace’s design shines across generations.
This confrontation is a tribute to fashion as history. Both stars wore the dress, proving that great designs get better with their wearers. It’s an eye-searing testament to style’s timelessness.
6. Sabrina Carpenter & Madonna in Bob Mackie
Sabrina Carpenter stunned at the 2024 VMAs in a Bob Mackie dress worn by Madonna to the 1991 Oscars. Madonna’s first outfit was pure showbiz, dripping with the glamour Mackie’s are famous for. It was a moment that perfectly captured her iconic career.
Carpenter’s 2025 reboot infused fresh youthfulness with a mix of retro flashiness and her own playful persona. Her styling was customized so that the dress appeared to be tailored for her. It’s a nod to Mackie’s genius at creating star-making garments.
It’s a moment of passing the torch between two generations. Both women added bling to the gown, but in extremely contrasting manners. Fashion’s ability to tie its icons together in time is alchemy.
7. Blake Lively & Britney Spears in Iconic Versace
Blake Lively’s It Ends With Us premiere look in 2024 was a tender homage to Britney Spears. She wore the colorful Versace dress Spears rocked in 2002, a rainbow-colored masterpiece from the spring/summer 2003 lineup. Lively’s choice was pure millennial nostalgia.
Spears’ initial Milan appearance was vintage early 2000s bold, colorful, and unapologetic. Vibrant, a self-proclaimed Britney fan, judged the dress Met-worthy, giving it cultural value. Her modern glamour honored the pop star’s roots.
- Nostalgic Tribute: Lively’s choice was a nod to Britney’s influence.
- Vibrant Pattern: Versace’s colors burst in both eras.
- Emotional Bond: The dress bridged fan and icon well.
This was not only style it was an affection letter to an era. Lively’s connection on an emotional level made it unforgettable. Both actresses sparkled, making style have stories to tell.
8. Brie Larson & Alexandra Daddario in Polka-Dotted Dôen
At the 2024 Filming Italy press conference, Brie Larson and Alexandra Daddario committed an adorable fashion gaffe, both appearing on the red carpet in the same black-and-white polka-dot Dôen dress. The timeless pattern was both playful and elegant, perfect for the event. It was a happenstance moment made for the tabloids.
Larson’s sleek, Oscar-winning attitude complemented Daddario’s laid-back, summery style. Subtle styling tweaks i.e., shoes or hair kept their separate identities. A playful sense of humor transformed an incipient faux pas into a humorous experience.
This 2025 image remembers fashion’s power to delight. Cross-generational style was showcased by the Dôen dress via both actresses. It’s a reminder that even missteps can be good style anecdotal.
9. Zendaya & Cindy Crawford in Vintage Ralph Lauren
Zendaya stunned at the 2024 Challengers photocall in a white Ralph Lauren gown that Cindy Crawford sported way back in 1991. Crawford’s strutting of the runway was pure ’90s elegance, distilling Lauren’s spotless, elegant sensibility. It was a masterclass of supermodeling.
Zendaya’s 2025 update had the dress appear modern but timeless, her chameleon self doing what it does best. Her updated version honored the gown’s history but in love with the moment. It’s fashion as a time machine.
- Runway Royalty: Crawford epitomized ’90s chic.
- Modern Muse: Zendaya’s hairstyle was new and of the moment.
- Timeless Design: Lauren’s creations look fabulous across the centuries.
This confrontation celebrates fashion’s cyclical nature. The two women enhanced the dress with each of their own charm. It speaks to fabulous design never going out of style, but waiting around for reinvention.
10. Sydney Sweeney & Angelina Jolie in 2004 Oscars Ivory Silk
Sydney Sweeney paid tribute to Angelina Jolie at the 2024 Vanity Fair Oscars After-Party, wearing the same ivory silk gown worn by Jolie in 2004. Jolie’s original look was almost otherworldly, a symbiotic blend of power and elegance. It’s an Oscar memory engraved in history.
Sweeney’s 2025 iteration brought youthful energy, her glamour decisions providing the iconic silhouette a fresh lease of life. The ageless charm of the dress served both actresses in full justice. It was a testament to Hollywood’s enduring glamour.
This homage spanned two generations of red-carpet royalty. Sweeney’s choice provided the gown’s lineage an additional push, justifying its magic. Both actresses made it unforgettable, each in her own limelight.
11. Angelina Jolie, Zahara Jolie-Pitt & Jane Fonda in Elie Saab Couture
Angelina Jolie looked stunning in an Elie Saab couture dress during the 2014 Oscars, its loveliness a beautiful match for her elegance. Zahara Jolie-Pitt wore it in 2021 to The Eternals premiere, a bittersweet mother-daughter memory. The dress was passed down as a family heirloom.
Jane Fonda finished off the trio, wearing a red version to the 2014 Cannes premiere of Grace of Monaco. Her red-hot statement and high-energy look received attention. Each woman added her own twist to the gown, testifying to its versatility.
- Family Legacy: Zahara’s wear also served up emotional resonance.
- Color Contrast: The red color chosen by Fonda radically altered the mood.
- Designer Magic: Elie Saab’s magic was also present in all three.
This multi-generational confrontation is fashion at its most authentic. How the gown transformed over the course of events and wearers is a testament to the power of design. Rocked it best? The answer’s in the story.
12. Zendaya & Michael B. Jordan in Berluti Suits
Zendaya broke the rules in a gray Berluti suit to a 2019 New York Fashion Week party, pairing mannish tailoring with ladylike polish. Michael B. Jordan slipped the very same suit on to the 2019 Oscars, exuding old-school leading-man charm. It was a heaven-made sartorial union.
Jordan’s sweet Instagram post “Zendaya hands down no contest” announced her the fashion winner. Her bold take defied fashion norms, and his dapper look was timeless. The suit proved its cross-gender versatility.
This 2025 retrospective praises fashion as genderless. Both stars projected confidence, but Zendaya’s snap stole the show. It’s proof that fashion won on the grounds of bold, personal expression.
13. Dua Lipa & Cindy Crawford in Harnessed Versace
Dua Lipa oozed ’90s attitude at the 2022 Grammys in a domesticated Versace dress, first worn by Cindy Crawford to the 1992 VMAs. Crawford’s original was authentic Versace slack, seductive, and cultish. It captured a decade’s unapologetic style.
Lipa’s 2025 update added modern cool, her pop-singer swagger bringing the cut back to life. Crawford’s Instagram nod “Then and now. Timeless” closed its legacy. The dress’s unapologetic spirit burst both decades.
This confrontation crosses eras in Versace’s fearless vision. Every celebrity’s sense of confidence made the look iconic. It’s a feat of fashion to cross old and new.
14. Shakira & Pink in Balmain Minidress
Shakira and Pink both sported the same black-and-silver Balmain minidress at the 2009 VMAs, a strapless showstopper perfect for the red carpet. Shakira’s sultry sensuality gave it life, her stage presence unquestionable. Pink’s rock-star attitude, with big jewelry and a flashy bouffant, gave it an alternate vibe.
Their humor turned a potential confrontation into a mythical moment, posing with guffaws. In 2025, this doppelganging is iconic among fans, showing fashion’s playfulness. The dress was twice as lovely with both stars.
- Red-Carpet Magic: Balmain’s design was made for fearless moments.
- Shared Joy: Theirs was the friendship that made the serendipity iconic.
- Personal Flair: Stylistic contrasts highlighted their personal sensibilities.
This final showdown proves fashion’s all about sharing, not borrowing. Shakira and Pink’s twinning moment is a love letter to the sassy spirit of style. Cheers to more twinning victories!
