The Best Celeb Vintage Fashion Moments Of The 2020s (So Far)

Vintage fashion has proved to be a major element of the 2020s fashion landscape, with more and more celebs turning to collections of the past to make a statement on the red carpet. This style approach has many appeals, ranging from the flex associated with accessing archived items to the element of sustainability that comes with wearing vintage. Hollywood figures who walk the red carpet in archived pieces also position themselves as part of fashion history. 

"Archival clothing holds not just moments in time but also the hours of creation — designers, teams, runway shows, and the personal collections they enter," Isabel Bonner, an archivist based in London, told Complex. "As these garments move into the archive phase, they continue to evolve through shoots, images, and red carpet moments, adding new layers to their story."

While this practice isn't always without controversy, see Kim Kardashian's wear of Marilyn Monroe's iconic birthday dress to the 2022 Met Gala, celebrities have proved that donning garments of the past can make for a real modern moment. Of course, some stars choose to wear recreations of classic pieces or take a more referential approach. With all this in mind, it's not surprising that some of the best fashion moments of the 2020s feature vintage. 

Olivia Rodrigo landed on the list of best vintage fashion moments of the 2020s when she visited the White House back in 2021, meeting with President Joe Biden and Dr. Anthony Fauci to discuss the importance of vaccines. The "Drivers License" singer stepped out in a pink, white, and black tweed skirt suit from Chanel's Spring 1995 collection, pairing the chic set with a pair of platform heels, black socks, and black box handbag. The look balanced Rodrigo's youthful playfulness and the formality of the setting, being compared to Cher's iconic plaid look from "Clueless," alongside the pink-wearing Jackie Kennedy. In this way, the choice of vintage definitely paid off.

In 2022, Bella Hadid attended a screening of "L'Innocent" at the Cannes Film Festival. The model looked absolutely beautiful in an archival dress featuring a strapless, ruched bodice and a velvet skirt dramatically draped with taffeta across the hips. The gown was originally designed by Gianni Versace for opera singer Helga Dernesch, with the Austrian donning the black gown for a performance of "Salomé at Teatro alla Scala" in 1987. Hadid styled the sculptural look with statement earrings, dramatic eyeliner, and a slicked back bun accented by a small bang. The celeb is no stranger to a vintage look, with this moment demonstrating the strength of her fashion prowess.

Next, Gabrielle Union was dripping in color when she stepped out at the NAACP Image Awards in 2023. The "Bring It On" actor posed in an archival piece from Atelier Versace's fall 1989 collection known as the "Circus" gown that featured vibrant, geometric shapes said to be inspired by Cyrk Polish circus poster art. The hand-beaded garment also consisted of a strapless, structured bodice and an ankle-length skirt, with the model accessorizing with pointed-toed heels and a choker-style necklace with a triangular pendant. Not only did Union call back to a famous moment in Gianni Versace's design history, she looked absolutely stunning while doing so.

Given that Zendaya lands among celebrities who take method dressing to the next level, it comes as no surprise that one of her press tour ensembles doubles as a chic vintage moment. She attended a photo call for "Challengers"in a skirt suit from Vivienne Westwood's spring/summer 1994 "Café Society" collection. The two-piece set consisted of a vest-style top striped with shades of blue, red, and white, and a matching miniskirt equipped with a feathered bustle. The preppy look is one of many Zendaya has pulled from the archives, making her place on the list of best vintage moments of the 2020s well-earned.

Not only has Ariana Grande channeled Audrey Hepburn throughout her lookbook, she's donned actual archival garments to walk the red carpet. The "7 Rings" singer wore a vintage Chanel dress from the brand's fall 1986 collection to Variety's 10 Directors To Watch and Creative Impact Awards in 2025. The black dress consisted of a structured round skirt that fell below the knee and a zig-zag neckline adorned with a bow and white flower. The celeb kept her styling classic, donning pointed-toed heels, black tights, and a string of pearls. Clearly, Grande has an eye for vintage.

Chappel Roan made her debut at the Grammy Awards in 2025, walking the red carpet in a head-turning Jean Paul Gaultier dress from 2003. The archival gown featured a high-low skirt trimmed with lengths of tulle and decorated with an Edgar Degas-inspired print of twirling ballerinas. The "Good Luck, Babe!" artist paired the vintage piece with dramatic makeup reminiscent of a porcelain doll and cyan gloves tipped with golden nails. With Roan ranking among the best-dressed celebs of 2024, it's not surprising that she continued to bring the drama with this vintage moment.

Next, Natalie Portman stepped out in a recreation of an iconic piece when attending the 2025 Cannes Film Festival. The floor-length dress was inspired by the "Mexique" gown from Dior's fall 1951 Haute Couture collection. It was designed with a silver strapless bodice tied with a black bow and an A-line skirt decorated with sparkly half-circles reminiscent of mermaid scales. The "Black Swan" star accessorized with dazzling diamond-encrusted jewelry and a slicked-back updo. While this is a recreation instead of an actual archival piece, it shines just as brightly as the original.

Keke Palmer channeled '90s It-Girl at the 2025 BET Awards, walking the red carpet in a minidress from Chanel's fall/winter 1993 collection. The black piece featured a halter-style neckline and a statement tulle train, with gold sequins bringing a playful shine. The "Nope" actor kept her accessories simple, wearing shiny, pointed-toed heels and styling her hair into a middle-parted bob. Palmer has worn several archival looks throughout the 2020s, with this party-ready ensemble definitely being a standout for its fun energy.