All of Zendaya’s Most Fashionable Moments

From her Disney days to the red carpet outfits that helped make the actress a certified fashion icon, Observer takes a look back at Zendaya’s most memorable style moments.

zendaya posing on red carpet
Zendaya is a red carpet chameleon. Getty Images

Zendaya’s chameleon-like ability on the red carpet has helped to make her as renowned for her fashion choices as she is for her acting and singing credits. The Euphoria star established herself as a style star to watch early on during her Disney days, when the then-teenager first turned to stylist Law Roach. A match made in Hollywood heaven, the duo has worked together ever since, with Roach effortlessly taking Zendaya from contemporary sets to vintage gowns. “We play dress-up and create outfits to make ourselves happy or to pay homage to the people we’re inspired by,” Roach previously told British Vogue. This playful approach to styling has helped to make Zendaya one of the most exciting stars on the red carpet, and it’s earned her some major fashion accolades and opportunities, too.

As a teenager, the actress and singer became the face of Madonna’s clothing line, Material Girl, in 2014. Less than two years later, she joined the CoverGirl family and landed a campaign with Michael Kors, before teaming up with Roach to launch her own shoe line, Daya by Zendaya, which quickly expanded into clothing. While the line is now defunct, it wasn’t Zendaya’s only endeavor in the design world. In 2018, the Spider-Man actress became the women’s ambassador for Tommy Hilfiger, and subsequently co-designed ‘70s-inspired capsule collections that made their way down the runway in 2019 (the first collection in Paris, and the second in New York City).

From there, the luxury partnerships really began to stack up. In 2019, Zendaya was named the face of Lancôme beauty, and the following year, she joined Bulgari and Valentino in ambassador roles. In between her fashion, jewelry and beauty campaigns, Zendaya and Law Roach continued to reinvent her style with a mix of custom and archival looks from designers like Fausto Puglisi, Vera Wang and Valentino—all of which helped the Emmy Award-winning actress become the youngest recipient of the Fashion Icon Award presented by the Council of Fashion Designers of America in 2021. 

And Zendaya is showing no signs of slowing down. Just when we’d gotten used to seeing her in Valentino, she switched things up when she was announced as the new ambassador for Louis Vuitton in the spring of 2023 (with a new campaign styled by Roach, too).

Ahead, we’ve rounded up all of Zendaya’s most memorable fashion moments (so far, that is)—from her first red carpet ensembles as a teen to her custom looks at the Met Gala, Academy Awards and beyond.

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zendaya wearing a pink dress with cardigan
Zendaya. Getty Images

2010, Disney TCA Party

In one of just a handful of red carpet looks that didn’t involve Law Roach, Zendaya attended an event for Disney at the start of her career in a lacy pale pink dress with all-black accessories.

zendaya wearing a pale green blazer and skirt
Zendaya. Getty Images

2011, ‘Justin Bieber: Never Say Never’ Premiere

Stylist Law Roach has cited this look as the beginning of his working relationship with Zendaya, who was starring on Disney’s Shake It Up at the time. To attend the premiere of Justin Bieber’s documentary, Roach and Zendaya chose a metallic Alice + Olivia blazer paired with a white top and blue mini skirt.

zendaya wearing metallic gold pants and white button up
Zendaya. FilmMagic

2012, ‘Teen Vogue’ Young Hollywood Party

For Teen Vogue’s annual Young Hollywood event, Zendaya went a more sophisticated route with a crisp white button-down blouse and a floor-length pleated gold skirt, which the Disney actress paired with a volumized ponytail and metallic smoky eye makeup.

zendaya wearing a white skirt and black leather jacket
Zendaya. FilmMagic

2013, ‘Black Nativity’ Premiere

Zendaya added a bit of edge to her polka dot tulle Chloe skirt with a black leather jacket and matching turtleneck. The otherwise neutral ensemble also got a pop of color, thanks to a pair of mint green Louboutins.

zendaya weaeing a blue skirt with sheer button up top
Zendaya. AFP via Getty Images

2014, Grammy Awards

Zendaya kept the skirt and top combo going a few months later when she attended her first Grammy Awards ceremony in Emanuel Ungaro. The sheer black blouse and coordinating teal and black polka dot skirt were part of then-creative director Fausto Puglisi’s spring 2014 collection, and Zendaya tied the look together with classic black Louboutin pumps and a black clutch.

zendaya wearing a black feathered dress with white top
Zendaya. FilmMagic

2014, Governors Awards

For the Governors Awards, Zendaya opted for classic glamour, wearing a strapless design from Christian Siriano’s fall 2014 collection. The subtly dramatic dress started with a white bodice that led to a feather-accented black skirt with an asymmetrical slit. The actress and singer matched her Louboutins to her matte red lip, and she kept her hair pulled back into a sleek low bun.

zendaya wearing a gold set with pale blue bra top
Zendaya. WireImage

2014, American Music Awards

Always one to reinvent her look, Zendaya ditched the dresses at the American Music Awards, and instead, wore a metallic trench coat and pants set from Georgine. The golden ensemble also included a mint bandeau top, and in keeping with the ’70s, Diana Ross-inspired theme, Zendaya accessorized with oversized hoop earrings and wore her hair in effortless curls.

zendaya wearing a white gown
Zendaya. WireImage

2015, Academy Awards

Zendaya’s Venus de Milo-esque Vivienne Westwood gown at the 2015 Academy Awards was a gorgeous moment, but it was her Lisa Bonet-inspired locs that ended up making the biggest statement (and later, led to her very own Barbie). The accessories also helped to make the look, with Zendaya pairing her ivory off-the-shoulder dress with a matching Vivienne Westwood clutch and Chopard jewelry.

zendaya wearing a red trail gown with volume and black top
Zendaya. Getty Images

2015, Met Gala

2015 was a fashion-defining year for Zendaya, who also attended her first Met Gala alongside designer Fausto Puglisi (one of her red carpet go-tos). To honor the “China: Through The Looking Glass” theme, Zendaya’s bespoke look—which included a black velvet bodice with a plunging neckline—featured a sun motif embroidered on her flared mini skirt, which continued through the train of the dress, and could even be seen in her arm cuff and headpiece accessories.

zendaya wearing a white dress with lips
Zendaya. WireImage

2015, Barbie Event

Months after her Academy Awards appearance, Zendaya was presented with her very own Barbie doll commemorating the look. For the big unveiling in Los Angeles, Zendaya wore a strapless white dress with a reddish-pink lip print that the actress matched to her pink lipstick.

zendaya wearing a gold floral dress and plaid train
Zendaya. David M. Benett

2015, Vivienne Westwood Show

Vivienne Westwood was a firm favorite of Zendaya’s early red carpet days, so naturally, the actress attended the fashion house’s spring 2016 show. Wearing a design from the previous season, Zendaya’s gold minidress was given a signature Westwood twist with a long train in red plaid.

zendaya wearing a floral pale pink set
Zendaya. AFP via Getty Images

2015, American Music Awards

At the AMAs, Zendaya went for head-to-toe hot pink with a floral lace skirt and blouse set from Emanuel Ungaro and matching Christian Louboutin So Kate pumps. Zendaya even kept her makeup on theme, with a matte pink lip that she did herself.

zendaya wearing a grey turtleneck sequin dress
Zendaya. WireImage

2015, ‘Star Wars: The Force Awakens’ Premiere

Zendaya turned the humble winter turtleneck into a red carpet-ready look when she paired the oversized sweater with a clear, crystal-embellished mini skirt (both by Michael Kors) for the Star Wars premiere. Strappy Jimmy Choo sandals, statement earrings and a chic bob completed the effortlessly cool ensemble.

zendaya wearing a deep red tiered gown
Zendaya. Getty Images

2016, Golden Globe Awards

In another first, Zendaya attended the 2016 Golden Globes in a princess-worthy tiered burgundy gown from Marchesa.

zendaya wearing a black suit with bang hair
Zendaya. WireImage

2016, Grammy Awards

The following month, Zendaya proved she’s not afraid of taking a fashion risk when she switched things up entirely with a David Bowie-inspired outfit at the Grammy Awards. Wearing a black Dsquared2 suit composed of wide-leg trousers and a double-breasted jacket, Zendaya’s beauty look once again became the most talked about component of her look, thanks to her honey-colored mullet.

zendaya wearing a leather skirt and red top
Zendaya. Getty Images

2016, Louis Vuitton Show

It would be another seven years before Zendaya officially joined Louis Vuitton as a house ambassador, but her attendance at the fall 2016 collection—dressed in a Louis Vuitton logo-embossed dress, no less—shows she’s been a longtime fan of the iconic French fashion house.

zendaya wearing a sparkle deep blue dress
Zendaya. Getty Images

2016, GLAAD Media Awards

Trying out another retro-inspired look, Zendaya attended the GLAAD Media Awards in a navy-blue David Koma dress that featured a crystal-embellished bodice and midi-length skirt with thigh-high slits. A midnight-blue smoky eye and Jimmy Choo sandals matched the dress, and Zendaya’s hair was styled into finger waves that were slicked back into a low knot at the back.

zendaya wearing white jeans and white bra and cardigan
Zendaya. Getty Images

2016, ‘Marie Claire’ Fresh Faces Party

Zendaya took a more casual approach to her next themed look, channeling the supermodels of the ‘90s with a vintage Chanel jacket and bralette that she paired with white jeans, Jimmy Choo pumps and a high ponytail.

zendaya wearing a blue and white pattern dress with cut outs
Zendaya. Getty Images

2016, CFDA/Vogue Fashion Fund Awards

Fresh off her Michael Kors campaign (and several months after attending the Met Gala with the designer), Zendaya attended the CFDA Awards in another Michael Kors look. This time, the actress opted for a floor-length navy dress from the spring 2017 collection, which featured side cutouts, white floral embroidery and flowy, off-the-shoulder sleeves.

zendaya wearing a black gown with pearls
Zendaya. FilmMagic

2017, Chrysalis Butterfly Ball

In 2017, Zendaya paid homage to trailblazing entertainer and civil rights activist Josephine Baker, in a pearl-embellished black dress and Baker-inspired finger waves.

zendaya wearing pinstripe pants and blazer
Zendaya. GC Images

2017, In New York City

While promoting her upcoming movie, Spider-Man: Homecoming, Zendaya arrived at the Good Morning America studios in a pinstripe suit that she styled casually, with a white shirt and white sneakers.

zendaya wearing a hot pink gown
Zendaya. FilmMagic

2017, ‘Spider-Man: Homecoming’ Premiere

Zendaya’s look was more Barbie than superhero at the Spider-Man: Homecoming premiere, thanks to her hot pink Ralph & Russo Couture gown. The bespoke dress featured a pleated bodice with an asymmetric neckline and a thigh-high slit at the skirt, plus a sweeping train.

zendaya wearing a white bejeweled gown
Zendaya. GC Images

2017, Paris Fashion Week

After attending Ralph & Russo’s fall 2017 show in Paris, Zendaya arrived at a party hosted by the fashion house looking very much like Audrey Hepburn in Sabrina with her embroidered white gown and navy-lined train, slicked back hair and Chopard diamonds.

zendaya wearing a black gown with sheer cut outs
Zendaya. Corbis via Getty Images

2017, British Fashion Awards

Zendaya’s Vivetta dress at the 2017 British Fashion Awards was equal parts classic and contemporary, with its floor-length black velvet silhouette, a sheer bodice with equestrian detailing and sleeves with crystal-embellished stars.

zendaya wearing a butterfly gown
Zendaya. WireImage

2017, ‘The Greatest Showman’ Australia Premiere

Zendaya sported several circus-themed looks throughout the press tour for her 2017 film The Greatest Showman (including a Ralph Lauren ringmaster suit), but this butterfly gown was the real standout. Part of Moschino’s spring 2018 collection, the dress quite literally resembled a monarch butterfly with its structured winged bodice in shades of orange, yellow and black.

zendaya wearing a beige trench with red outfit
Zendaya. Getty Images for Michael Kors

2018, Michael Kors Show

To sit front row at the presentation of Michael Kors’ fall 2018 collection, Zendaya sported a look straight off the runway. The dressed-up take on athleisure wear included a red tracksuit and a trench cape coat, which Zendaya styled with a pair of white pumps that tied in with the tracksuit’s white stripes, and a glossy red lip.

zendaya wearing chain metal dress
Zendaya. Karwai Tang/Getty Images
zendaya wearing a chain metal dress
Zendaya. Getty Images for The Hollywood R

2018, Met Gala

Zendaya is always one to watch at the Met Gala, but her modern-day Joan of Arc look for the “Heavenly Bodies: Fashion and the Catholic Imagination” theme in 2018 remains her best. While a Jules Bastien-Lepage Joan of Arc painting in the Met depicts the saint before she led the French army to victory over the English, Zendaya’s custom Versace dress drew inspiration from Joan of Arc’s medieval military garb. Featuring a structured neck plate and gunmetal chainmail bodice embellished with Swarovski crystals, the gown also included a beaded silk chiffon skirt, which Zendaya styled with a blunt bob and bangs.

zendaya wearing a floral dress with brown belt and botts
Zendaya. Corbis via Getty Images

2019, Tommy Hilfiger x Zendaya

After being announced as the women’s ambassador for Tommy Hilfiger in 2018, Zendaya presented her first TommyNow collection in Paris with a cast of Black models ranging in age from 18 to 70. To celebrate the debut of her first ’70s-inspired collection (the second shown as part of New York Fashion Week six months later), Zendaya was spotted ahead of the runway show in a patterned dress and burgundy over-the-knee boots from the capsule.

zendaya wearing a blue light up gown
Zendaya. Getty Images for The Met Museum/
zendaya wearing a light-up blue gown
Zendaya and Law Roach. FilmMagic

2019, Met Gala

Roach has said that this Met Gala moment was dreamed up as a way to pay homage to Zendaya’s history with Disney, while also following the 2019 camp theme. Zendaya and Roach (who Zendaya often refers to as her fairy godbrother) put on a show when they arrived on the pink carpet, with the actress’ Cinderella-inspired ball gown transforming into a design that literally lit up with a wave of Roach’s magic wand. The custom design was created by Tommy Hilfiger, and reportedly took three months to engineer with LED lights. The detailed look also included glass slippers by Tommy Hilfiger and a crystal-encrusted clutch by Judith Leiber that replicated Cinderella’s pumpkin carriage.

zendaya wearing a white fluffy dress
Zendaya. WireImage,

2019, ‘Euphoria’ Premiere

Though Euphoria proved to be a bold departure from Zendaya’s Disney days, the premiere let everyone know that she would continue to bring us big fashion moments. The actress chose a white mini dress from the Nina Ricci fall 2019 collection that was anything but ordinary, with shimmering organza ruffle detailing.

zendaya wearing a suit with fitted blazer
Zendaya. AFP via Getty Images

2019, ‘Spider-Man: Far From Home’ Photocall

For her return to the Spider-Man series, Zendaya kicked things off in London wearing a tailored three-piece suit from Alexandre Vauthier and newly-dyed auburn tresses.

zendaya wearing a black and red dress with cut outs
Zendaya. FilmMagic

2019, ‘Spider-Man: Far From Home’ Premiere

Spider-Man was very much the inspiration for Zendaya’s look at the Los Angeles premiere for the film, where she posed on the red carpet in a sequined gown from the Armani Privé spring 2019 couture collection. The red and white dress featured a dramatic open back, and because of all its embellishment, Zendaya kept the accessories to a minimum with black Louboutin pumps and simple earrings.

zendaya wearing a cropped button up and black pants
Zendaya. Getty Images

2019, Giorgio Armani Privé Show

Following her Armani red carpet look at the Spider-Man premiere, Zendaya headed to Paris for the fashion house’s fall 2019 couture show. This time opting for a suit, Zendaya’s custom Armani ensemble included an ab-baring tuxedo shirt and high-waisted trousers, which the actress paired with black Louboutins.

zendaya wearing a deep green silk gown
Zendaya. AFP via Getty Images

2019, Emmy Awards

For the 2019 Emmy Awards, Zendaya paired her red hair with an emerald gown by Vera Wang. The bespoke look featured a fitted corset as well as a silk skirt with a thigh-high slit, and Roach turned to Brian Atwood for custom silk emerald pumps and Cartier for diamond and emerald earrings and a diamond cuff.

zendaya wearing a black cut out gown with jewel lining
Zendaya. Getty Images

2019, People’s Choice Awards

Zendaya took home two awards at the PCAs for her role as Rue Bennett in Euphoria, and she was also one of the evening’s best-dressed in a classic black Christopher Esber gown that featured a touch of sparkle thanks to crystal-trimmed cutout detailing. Zendaya completed the look with her go-to black Louboutins, a bold matte orange lip and slicked-back top knot.

zendaya wearing a pink tow piece with metallic bodice
Zendaya. WireImage

2020, Critics’ Choice Awards

Adding a bit of edge to her usual pink looks, Zendaya attended the 2020 Critics’ Choice Awards in a fuchsia maxi skirt and matching breastplate from Tom Ford’s spring 2020 collection. To get the fit just right, Zendaya shared that the metallic breastplate had to be molded to her body, and she decided to match her makeup to the two-piece set with a shimmering pink smoky eye.

zendaya wearing a puffed silk blue top with black skirt
Zendaya. Getty Images for ESSENCE

2021, ‘Essence’ Black Women In Hollywood

Zendaya was one of the honorees at the Essence Black Women In Hollywood event in 2021, and she and Roach decided to go vintage for the occasion with a Yves Saint Laurent Haute Couture gown from 1982. The design, which was originally owned by Eunice Johnson, an entrepreneur who founded the Ebony Fashion Fair and Ebony magazine, featured an icy blue silk top with exaggerated shoulders and a black floor-length skirt with a slit at the bottom.

zendaya wearing a bright yellow two piece dress
Zendaya. Getty Images

2021, Academy Awards

In 2020, Zendaya landed a luxury fashion campaign with Valentino and a luxury jewelry campaign with Bulgari, and she wore both brands to the 2021 Academy Awards. Her fluorescent-yellow chiffon gown required 300 hours of work, thanks to its elaborate draping. Zendaya paired the strapless design with a diamond and platinum necklace by Bulgari, leaving her waist-length hair down in tousled waves and opting for barely-there makeup.

zendaya wearing a color blocked romper
Zendaya. AFP via Getty Images

2021, ‘Space Jam: A New Legacy’ Premiere

No one does a theme quite like Zendaya, and for the Los Angeles premiere of Space Jam: A New Legacy, she brought Lola Bunny (the cartoon whom she voices in the movie) to life. The sporty high ponytail was clearly a given, but Zendaya gave Lola’s colorful jerseys a high fashion spin with her bright color-block silk jacket and shorts set from Moschino’s 2022 resort collection.

zendaya wearing a beige skin-tight gown
Zendaya. Getty Images

2021, Venice International Film Festival

Zendaya upped her fashion game once again when she showed up at the Venice International Film Festival in this nude Balmain dress. While the bespoke design (and her complementary wet hairstyle) looked as though the actress had just emerged from the Grand Canal, the dress was actually made from leather that was crafted to fit Zendaya’s body like a second skin. Nude Louboutins perfectly coordinated with the dress, and Zendaya’s Bulgari Serpenti necklace served as the only pop of color, with its astonishing 93.83 carats of emeralds (the actress was the very first person to wear the Magnifica Serpenti Hypnotic Emerald necklace).

zendaya wearing a red two-piece dress
Zendaya. WireImage

2021, CFDA Fashion Awards

A high-fashion moment was essential for Zendaya, who was receiving the Fashion Icon Award, at the 2021 CFDAs. For the special occasion, she and Roach doubled down on the bold elements with a bold red two-piece ensemble from Vera Wang that put the actress’ abs on full display. The silk number was composed of a bandeau bra and floor-length fitted skirt with a bubble waist, and Zendaya completed the look with a bright red manicure, plenty of Bulgari diamonds and long box braids that went below her waist.

Zendaya wearing a black dress with open back
Zendaya. WireImage
zendaya wearing a black dress
Zendaya. AFP via Getty Images

2021, Ballon D’Or Paris Award Ceremony

While in Paris, Zendaya perfectly executed another vintage moment—this time, in a Roberto Cavalli fall 2000 gown that was given an update from the fashion house’s current creative director, Fausto Puglisi. The black column dress seemed classic enough from the front, but as Zendaya turned to pose, she revealed intricate gold detailing at the back that appeared to resemble a spinal cord. Black pumps and oversized gold hoop earrings rounded out the look, and Zendaya wore her hair in a faux bob to better show off the gown’s elaborate golden spine.

zendaya wearing a beige spider web dress
Zendaya. Getty Images

2021, ‘Spider-Man: No Way Home’ Premiere

For the Los Angeles premiere of her latest Spider-Man film, Zendaya turned to Valentino for a custom gown (and mask!) that was embroidered with a spider web motif.

zendaya wearing a cropped button top and glitter full skirt
Zendaya. FilmMagic

2022, Academy Awards

Leave it to Zendaya and Roach to come up with a totally unexpected, instant hit of a look. For the 2022 Academy Awards, the actress wore a bespoke two-piece set from Valentino that featured a white silk satin cropped shirt and a flowing silver organza skirt that came with its own train. To match the sequin embroidery on her skirt, Zendaya sported a silver manicure and silver eyeshadow, and she also chose several stunning diamond and white gold pieces from Bulgari, including a Serpenti necklace and multiple Serpenti Viper bracelets.

zendaya wearing a black and blue pattern dress
Zendaya. AFP via Getty Images

2022, ‘Time’ 100 Gala

Zendaya turned to the Bob Mackie archives for the Time 100 Gala, working with Roach to select a strapless teal and turquoise silk faille gown from the designer’s fall 1998 collection. To match the panels of deep green velvet in the dress, Zendaya lined her eyes with a matching shimmering emerald color, and she added even more sparkle with Bulgari diamond stud earrings, a necklace and rings.

zendaya wearing a full black gown
Zendaya. Getty Images
zendaya wearing a full black dress
Zendaya. Getty Images

2022, Emmy Awards

In 2020, Zendaya became the youngest actress to win the Emmy for Lead Actress in a Drama Series, thanks to her work in Euphoria. And she made history once again when she took home the award for a second time, dressed in an elegant Valentino gown that was custom-made for the occasion by the fashion house’s creative director, Pierpaolo Piccioli. The strapless black satin dress was inspired by a red look designed by Valentino himself from the fall 1987 collection. Grace Kelly served as the reference point for Zendaya’s polished waves, which were accessorized with a black silk ribbon, and the actress added Bulgari jewelry to finish off the look (including a white gold necklace with more than 17 carats of diamonds).

zendaya wearing a black encrusted body tight
Zendaya. WireImage

2022, Valentino Show

To attend the Paris Fashion Week show for Valentino’s spring 2023 collection (where she sat front row alongside Naomi Campbell), Zendaya wore a black ensemble that was entirely emblazoned with the Italian fashion house’s logo. The edgy look featured a sheer, crystal-embellished bodysuit that was worn under a matching oversized sequined blazer and shorts set.

zendaya wearing a black and green gown
Zendaya. WireImage
zendaya wearing a star white two-piece
Zendaya. Getty Images for BET

2023, NAACP Image Awards

Zendaya wore two vintage looks at the NAACP Image Awards in 2023 (an event that she first attended more than a decade earlier). To walk the red carpet, Zendaya turned to Versace’s spring 2002 couture collection for a strapless black gown that featured neon green accents, a plunging neckline and a thigh-high slit at the center of the skirt. But when it came time to present an award during the ceremony, Zendaya switched things up entirely in a white two-piece set inspired by a design from the Prada spring 1993 collection, and customized for the actress. While the original look included a halter-style bralette and pants with star-shaped inlays, Zendaya’s version paired a silk bralette with a floor-length skirt.

zendaya wearing a pale pink rose gown
Zendaya. WireImage

2023, Screen Actors Guild Awards

In one of her most stunning Old Hollywood moments, Zendaya attended the Screen Actors Guild Awards in a custom Valentino gown. The strapless pink design took more than 1,000 hours to craft and included 190 hand-embroidered silk roses of various sizes sewn throughout the train. In keeping with the theme, Zendaya wore her hair in a side-parted bob, which was styled in retro waves and paired with blush makeup tones and dramatic lashes. Bulgari jewelry completed the look, the highlight of which was a massive cushion tanzanite, morganite and aquamarine gemstone necklace.

zendaya wearing a black gown
Zendaya. Getty Images for Bulgari

2023, Bulgari Event

While attending a Bulgari event in Venice, Zendaya went for classic glamour in a custom black silk and velvet gown by Richard Quinn. The off-the-shoulder silhouette was also the perfect way to showcase Zendaya’s yellow diamond Serpenti necklace from Bulgari, which featured a massive 15.5-carat yellow diamond.

All of Zendaya’s Most Fashionable Moments