:max_bytes(150000):strip_icc()/040925-celeb-vintage-outfits-soc-d80ad48206f440db8a91750fd074b4e3.jpg "10 Best Celebrity Vintage Fashion Moments")
Fashion, by nature, is a cyclical business. Trends fade in and out; brands rise and fall, and rise again; past models of the moment reappear on the runway years later. But lately, the industry is not only borrowing past ideas from itself—it’s literally diving into its archives to resurrect exact looks of the past for a whole new generation to enjoy. Celebrity vintage outfits are everywhere these days, and each one has a story behind it that’s better than the last.
Following A-lister style is basically like taking a course in fashion history: That sparkly little skirt that Oliva Rodrigo wore when launching Guts a few years ago? The one that could’ve been of-the-rack Guizio? Turns out it was from the biggest 1990s designer you’ve never heard of. And those rockstar-sexy Y2K leather pants Bella Hadid slid into for a casual NYC stroll last summer? Not only are they from one of the era’s most influential brands, but were previously worn by none other than (an 18-year-old) Gisele Bündchen.
Below, more on these notable archival looks spotted—and others worth putting on your radar—and the fashion nerd 411 on each.
Kaia Gerber in Donna Karan
Sonia Recchia/Getty Images
As the daughter of one of the world’s biggest supermodels, Kaia Gerber’s vintage fashion choices always garner some extra scrutiny—especially if it looks like something her mother might’ve worn. This was certainly the case with the plunging Donna Karan gown she chose for the September 2024 Toronto Film Festival premiere of her movie Saturday Night: Straight from the New York designer’s 2003 archive, the piece could’ve been lifted straight from Cindy Crawford’s early aughts closet. Gerber made the look her own, though, with a stack of golden bangles and long, loose wavy hair. (Side note: A few days later, Gerber showed up to another event dressed in a modern-day recreation of her mom’s white Hervé Leger bandage dress from the 1993 Academy Awards.)
Zendaya in Vivienne Westwood
Jeff Spicer/Getty Images
Throughout her longtime collaboration with stylist and self-named “image architect” Law Roach, Zendaya has mined some of the best looks of fashion history for her red carpet purposes. This sassy little pinstripe suit from Vivianne Westwood’s spring 1994 show (which the pair picked for an April 2024 Challengers photo call in London) stands out as a highlight thanks to its feather bustle skirt and deep ties to pop culture: Sarah Jessica Parker wore a satin green version the mini with a white shirt tucked in as Carrie Bradshaw in an episode of Sex and the City.
Kylie Jenner in Atelier Versace
Getty Images
If Kylie Jenner’s PDA-filled night with Timothée Chalet at the January 2025 Golden Globes was the evening’s first topic of conversation, the reality star’s dress was the second. Lifted from Atelier Versace’s 1999 collection, the shimmering silver number was a straight-up homage to the dress Elizabeth Hurley wore to the CFDAs with Hugh Grant that same year.
Bella Hadid in Gucci
Gotham/GC Images
Model Bella Hadid has a long-documented track record of wearing historic pieces from major early 2000s labels (Roberto Cavalli, John Galliano, and Bluemarine seem to be some of her favorites). So it totally tracked that she’d gravitate toward these showstopping green leather pants from Tom Ford’s Fall 1999 line-up for Gucci while leaving New York City’s Bowery Hotel in July 2024. Fun fact: Gisele wore the same ones over two decades ago in a Western-themed editorial.
Emily Ratajkowski in Dior
Gotham/FilmMagic
Every fashion-obsessed corner of the internet nearly imploded with buzz when Emily Ratajkowski showed up to a New York Fashion Week event wearing this newspaper print slip dress. Not only is the piece from John Galliano’s spring/summer 2000 couture show for Dior (which was, quite controversially, inspired by homeless people sleeping on the streets of Paris), but it was very similar to a style Carrie Bradshaw famously wore on Sex and the City from the same collection.
Chappell Roan in Jean Paul Gaultier
Axelle/Bauer-Griffin/FilmMagic
Given singer Chappell Roan’s larger-than-life stage presence, this tulle gown covered in a Degas-inspired print from Jean Paul Gaultier’s spring/summer couture show was a fitting choice. She leaned right into the look’s drama by pairing it with a full face of highly stylized makeup (including a white skin tint and extra-long lashes) and—as originally shown on the runway—adding long gloves and a feathered headdress.
Rihanna in Maison Margiela
Instagram @badgalriri
In a recent Instagram post highlighting her look for a March 2025 trip to Barbados, Rihanna is pictured wearing an oversized tourist T-shirt dress covered in a beach landscape. But this is not just any old tee—it’s straight from Maison Margiela’s 2010 spring collection. This particular season was a memorable one for the brand as it occurred directly after the label’s founding designer announced he would be exiting the brand; no one knew whether he had a hand in this particular show or not.
Sabrina Carpenter in Chanel
XNY/Star Max/GC Images
Fresh off the December 2024 news she had split from her boyfriend, and “Please, Please, Please” co-star, Barry Keoghan, singer Sabrina Carpenter stepped out in New York in the ultimate single girl look: a fur-trimmed look from Chanel’s Fall 2024 season. An even bigger flex? The outfit was originally worn by Naomi Campbell on the catwalk.
Miley Cyrus in Bob Mackie
VALERIE MACON/AFP via Getty Images
Channeling a Barbarella-era Jane Fonda, singer Miley Cyrus shimmered and shimmied on-stage in an archival Bob Mackie dress at the February 2024 Grammy Awards. The sparkling showpiece was from the designer’s 2002 collection, titled To Broadway With Love—the look specifically referenced the song “Big Spender” from the 1960s musical Sweet Charity.
Olivia Rodrigo in Todd Oldam
Instagram @oliviarodrigo
While celebrating the September 2023 launch of her second album, Guts, Olivia Rodrigo was spotted in a cropped shirt and sparkly skirt set from Todd Oldam’s Fall 1995 collection (on loan from the designer himself). Although the brand has been shuttered for years now, the show this particular look came from has lived on through social media—specifically a clip of supers Shalom Harlow and Amber Valetta strutting the runway in these exact two pieces.
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