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Zendaya’s 10 Best Vintage Fashion Moments to Date

Zendaya rarely fails when it comes to fashion. Alongside collaborator Law Roach, the actress has proven the staying power of vintage clothes.

Zendaya's bet fashion moments
Photo-illustration by Oleksandra Nazarova

The looks that prove the actress does archival fashion best!

It is no secret that Zendaya rarely fails when it comes to fashion. She is regularly praised by the fashion press for her style and the actress has become synonymous with fashionable. Over the years, we have watched Zendaya (and longtime collaborator, Law Roach) move away from her “safe” Disney Channel persona, using fashion to do so. What has come to set her even further apart is the archival looks she has become known to wear.

The actress stars in Dune: Part Two, which premieres this weekend in UK cinema. The press tour behind the movie has generated a lot of buzz, with a significant amount coming from Zendaya’s fashion. The internet went wild when she stepped out at the London premiere in a bionic fembot suit from the AW95 Thierry Mugler collection. This is not the first time her choice of vintage fashion has been the center of attention. Here is a look back on some of her most iconic vintage looks!

1. Versace Spring/Summer 2003

In a homage to her own inspiration, Zendaya paid tribute to singer Beyoncé at the BET Awards in 2021. The actress wore a maxi-length version of a mini-dress which the “Crazy in Love” singer had worn 18 years earlier at the same ceremony. Stylist Law Roach said of the look: “Paying homage to the Queen Beyoncé wearing @versace SS2003 ….. get you a stylist with an ARCHIVE!!!!”

2. Valentino Spring/Summer 1992

During the photo call for the second season of her hit HBO show Euphoria in 2022, Zendaya once again led the fashion headlines in this black and white striped strapless gown. From the sculpted gown to the auburn hair, Roach and Zendaya seemed to dedicate the look to 90s supermodel Linda Evangelista, who first debuted the gown on the runway in 1991.

3. Roberto Cavalli Fall/Winter 2000

Forever staying on theme, it was widely theorized that during the press tour for Spider-Man: No Way Home, Zendaya’s looks were emulating the superhero’s greatest villains. Whilst attending the annual Ballon D’Or football ceremony in 2021, the actress put a twist on the attire of Spider-Man’s foe, Dr. Octopus. Fans were quick to draw comparisons between the villain’s costume and Zendaya’s avant-garde black dress and its gold skeletal back detailing.

4. Balmain Couture 1956

Not limiting herself to the fashion history of more recent memory, the actress went back more than 60 years to recapture some Old Hollywood glamour with this look. Roach and Zendaya were given access to explore the French fashion house’s extensive archives by Balmain’s creative director Olivier Rousteing. Worn to the 2022 NAACP Image Awards, she shared a portrait of her wearing the gown, breathing new life into this classic look.

5. Yves Saint Laurent Haute Couture 1982

While attending Essence’s 2021 Black Woman in Hollywood Awards, the actress wore this silk two-piece gown in celebration of its original owner: pioneering businesswoman Eunice W. Johnson. This powerful fashion tribute was pulled from Roach’s own personal archive, who shared a photo of the dress’s original label for Johnson to Instagram in an added dedication to the creator of Ebony Fashion Fair in 1958.

6. Versace Fall/Winter 2001

Before picking up the Star of the Year Award at CinemaCon in 2023, the Euphoria star walked the red carpet in this multi-textured dress. Combining a leather harness with a lace pattern, the look was a new take on its debut on the runway in 2001, worn by Karolina Kurkova. The actress made the look her own with added Bulgari jewels and matching leather pumps.

7. Bob Mackie Couture Fall/Winter 1998

After being given rare access to the Bob Mackie archives, Roach dressed Zendaya in this “vintage teal and turquoise silk faille, emerald velvet strapless couture ball gown” for the 2022 TIME100 Gala. Mackie was a designer the actress had previously spoken about a desire to work with. She said in an interview, that the one fashion celebrity closet she wanted to walk into was Cher’s for “all that custom Bob Mackie…I want all of that.”

8. Versace Couture Spring/Summer 2002

Once again in Versace, Zendaya walked the NAACP Image Awards carpet in 2023 in this unique lime and black gown. This was the first of two archival looks she wore to this event. This dress was originally planned to be worn when presenting an award, according to the actress. In a recent interview with Harper’s BAZAAR, they explained, “[en route to the red carpet] something in my brain said, I have to switch these.”

9. Prada Spring/Summer 1993

That first look she switched out at the NAACP Image Awards carpet was not forgotten! The two-piece was a recreation of a Prada two-piece by designer Miuccia Prada. Originally a bra top and trousers worn down the runway by supermodel Yasmeen Ghuari, the Malcolm & Marie star opted for a floor-length skirt instead. The ensemble was adorned with the original star-shaped motif from the 90s look.

10. Versace Fall/Winter 1996

Attending the virtual 2020 Green Carpet Fashion Awards, the actress championed sustainability by wearing this beaded silk gown. Roach had chosen a gown that was important personally as well as professionally. The dress was taken from a collection that debuted the year Zendaya was born. Similar versions of the dress have been worn by the likes of Kate Moss and Naomi Campbell in a look Roach described as totally “inspired by ’90s supermodels.” At the event, she picked up (via hologram) the Visionary Award, recognizing her exceptional endeavors in vintage fashion.

Does Zendaya prove that vintage fashion is here to stay?

With these iconic archival looks, Law Roach never shies away from the roots of these looks and their importance. These homages and the new effortless style that Zendaya brings to them cement her place in fashion history. It proves her collaboration with Roach to be a masterful match made in heaven. Together, the duo always manage to find a perfect medium that never fails to draw a lot (if not all) of the attention.

In the media, there have long since been reports questioning the staying power of vintage fashion, previously dismissed as a “red-carpet trend”. However, with Zendaya around, this “trend” is here to stay.

Written By

My name is Martha Matthews (she/her) and I am a third-year English Literature student at University College London. At Trill Mag, I write for Trending News, Entertainment & Culture. Besides writing, I love taking photos, going to art galleries and watching new (and old) films.

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