Zendaya's 32 Best Fashion Moments

Zendaya: undisputed fashion queen. The singer, actor, and dancer known mononymously (which means she's already iconic) has brought out so, so many brilliant styles that it's honestly hard to pick which ones are the best. The 2021 CFDA Fashion Icon Award recipient shuts the red carpet down whenever she's on it—and, of course, she's got great business and business-casual style too. She's a bit of a fashion chameleon: Who else could pull off old Hollywood glam, cutouts galore (for the Oscars!!), and literal Joan of Arc cosplay?

Zendaya's long-time stylist and image architect Law Roach, who referred to himself as her "creative director" in 2023, originally helped get the young starlet on the map when she was just 13 and still a Disney star. He later admitted that he helped get couture gowns for the up-and-comer by requesting gowns that had already been worn by another celebrity, causing her to become a staple of the "who wore it better?" style stories (and often winning, because, it's her). Once she was a known entity, though, everyone wanted to dress her. And she's been giving us red carpet magic every since.

Ahead, 32 iconic Zendaya outfits, from the prim and proper to the edgy and fun.

At the Screen Actors Guild Awards, 2023

This Valentino is a little softer and more "feminine" than Zendaya sometimes does. But the old Hollywood glam is strong in the choices here, with a few tiny rosettes starting at the waist and turning into a whole rosebush by the bottom. Pairing it with minimal jewelry, soft waves, gorgeous Bulgari jewels, and matching pink makeup big eyelashes, she somehow keeps this from looking twee and instead imbues it with retro glamour.

At the 2018 Academy Awards

She's a Grecian goddess—just in a cool chocolate-y brown color! This Giambattista Valli Haute Couture gown (paired with Bulgari jewelry) is deceptively simple. Without the panache Zendaya brings to it, the dress might feel a little too relaxed for the Oscars. But the key is in the styling, with the "formal but fun" topknot and very bronzy makeup to match. The ruching on the dress is actually more complex than at first glance, making this the opposite of a "Monet" (Clueless reference for the win!).

At the Primetime Emmys, 2022

This is the dress in which Zendaya made history. She became the first Black woman and the youngest person ever to win the Outstanding Lead Actress award twice, and—naturally—she appeared in full-on old-Hollywood glamour to collect her award. Believe it or not, Law Roach told Vogue that her final gown selection wasn't settled until just before the ceremony. The gown came to her in a dream, they approached Valentino to make it, and construction took about a week.

At the 2019 Met Gala

For the "Celebrating Camp: Notes on Fashion" Met Gala, Zendaya showed up as a literal modern-day Cinderella. Roach played the part of her fairy godmother, waving a wand to reveal a light-up element to the blue and white Tommy Hilfiger dress. Bonus: a bag in the shape of Cinderella's carriage! Zendaya later revealed that she was stressed out the whole time—the gown wasn't totally ready and needed "a week more" of work, as it was supposed to have more lights. Still looks amazing.

At the 2022 TIME100 Gala

If you're going to dip into the Bob Mackie archives (in case you missed it, he famously worked with icons including Madonna and Cher), do it in this gorgeous green and black dress—with Bulgari jewels and matching teal eyeshadow, naturally. Mackie shared on Instagram that the dress originated from the Fall 1998 collection; Roach shared on Instagram, "Vintage and Archival dressing isn’t a trend for me it’s what lead [sic] me to this career and will always be my first choice when possible."

At the Ballon D'Or Photocall, 2021

This dress was divisive, and it's easy to see why: The vintage Roberto Cavalli gown, from the autumn 2000 collection, has a goooorgeous gold skeletal detail down the back. It was "reedited" by creative director Fausto Puglisi, and some experts were a little distracted by the very visible thread that held the piece to the dress. But you can't fault the audacity of the look (and the thematic nature of it, since Zendaya has very famously starred in Spider-Man movies).

At the Louis Vuitton Womenswear Spring/Summer 2024 Show, 2023

This is...absolutely black-belt level fashion right here. The cool two-way zipper effect is such that it gives a dash of deep v-neck and thigh-high split at the same time (seriously, if it were unzipped one inch more the whole thing would be too much—but as-is, it's exactly right). Zendaya is an ambassador for Louis Vuitton, so it makes sense that 1) she'd be at their show, 2) she'd be wearing one of their dresses, and 3) as usual, she'd be the coolest-looking person there.

At the 2019 Emmys

The open corset gown really had a moment in 2019, and Zendaya here is delivering the best possible version of it. It's Vera Wang (with Cartier jewelry), but the accessories are super-simple so that the focus can be on the gown. The more intuitive choice might be to pair the outfit with a chunkier necklace, but here the dress is the detail on the upper half of her body. Her red hair is a perfect contrast, but doesn't look Christmassy in the color combination.

At the 2021 CFDA Fashion Awards

To accept her Council of Fashion Designers of America (CFDA) award—which made her the youngest to receive the award, Zendaya went in a daring red outfit. For most people, the extreme bubble skirt might make us look a little like a lollipop. Not Zendaya though! It's Vera Wang Haute Couture, and 60 carats of Bulgari diamonds—ahhmazing. As the CFDA correctly put it, her "journey to Fashion Icon superstar happened at supersonic speed."

At the NAACP Image Awards, 2023

Most people who'd wear this gown would give off major Beetlejuice vibes (actually, Zendaya later shared that it was inspired by Kim Possible, which is way cooler). This lime green and black Versace originated from their spring/summer 2002 collection, making it a gorgeous vintage pick. She later debuted a second outfit at the event, a reworked white Prada SS1993 cutout top and skirt, so it's vintage x2!

At the Academy Awards, 2015

For Zendaya's first Oscars, she kept it chic and simple, with a cream silky Vivienne Westwood, matching accessories, and long, elegant dreadlocks. It's timeless, it's chic, and it's the exact right balance between simple and striking. Let's not forget she's only 18 here! (If you'll remember, then-Fashion Police cohost Giuliana Rancic said something offensive about her hair, and Zendaya responded in an incredibly adult and honest way.)

At the 'Spider-Man: Homecoming' Premiere, 2017

One of Zendaya's tried-and-true colors, bright pink is associated with some of her most well-known outfits. This Ralph & Russo dress has a lot happening, including a v-neck at the top, side slit that went all the up to her hip, and a thin pink train at the back (Zendaya even did that thing where she pulled it up and tossed it to the side for some fun images). It's reminiscent of a gown that Jennifer Lopez wore to the 2018 AMAs, which means, I think, that Zendaya is keeping up with the most stylish people of all time.

At the CinemaCon Big Screen Achievement Awards, 2023

Leather and lace, literally! This is vintage Versace, from their fall-winter 2001 collection, originally worn by Karolina Kurkova on the runway (this is a tough "who wore it best," but I'm going to give it to Zendaya). Like many of her gowns, this is second-skin and fits like a glove, but somehow it feels sleek instead of body-con. Zendaya kept things tonal in her shoes and makeup, and even her hair highlights match the color scheme. Chef's kiss.

At the 'Euphoria' Season 2 Photo Call, 2022

Black and white stripes are a choice: you're a hair's breath away from looking like a very stylish referee or perhaps a wide-stripe zebra. But Zendaya is none of these things in (what else) vintage Valentino. Originally, supermodel Linda Evangelista wore the outfit on the runway in bright red hair—and it looks like Zendaya's red tresses may be a direct nod to the moment. She was there with her stylishly dressed Euphoria costars, so an edgy callback look was exactly appropriate.

At the Academy Awards, 2021

I mean...how she managed to make it look like she had her own personal wind machine, I'll never know, but even without the literally windswept hair, Zendaya's yellow cutout Valentino gown is an absolute standout. Roach called it a "neon dream," and (unlike in some ceremonies past) Zendaya really leaned in on the jewelry styling. In total, she wore 183 carats of yellow diamond Bulgari jewels—costing reportedly $6 million. Look at the necklace!!

At the Academy Awards, 2022

Zendaya's Valentino ensemble—a cutout white collared top and silvery glitter skirt—drew comparisons to another famous Oscars look (Sharon Stone in 1998, who famously defined high-low fashion with a collared shirt from the Gap). What's also cool about this particular pairing is that it's formal, as befitting the most upscale event Hollywood has every year, but it is still highly daring with its impressively high cutout. Very Zendaya.

At the Valentino Womenswear Fall/Winter 2022/2023, 2022

Barbie could never! (Actually, petition to get Zendaya to star in a Barbie sequel.) Anyways, while wearing an ensemble from the Paris Fashion Week Valentino collection she was attending—she literally matched the models, which is the meta cool moment we love to see—she makes the bright and beautiful hue look like it's not even a big deal. In some photos, she posed with a matching long pink jacket. It's tonal in the very best way.

At the Pre-Oscar Dinner, 2016

This was a "one event, wearing two outfits" kind of night. Both were Marchesa: The first was a nude floral gown, and the second (which I wholeheartedly love) has a feathered bustier and tulle skirt. It looks all-white, but if you look closely, you'll see that it's got subtle pastel colors all throughout. Since this was back in 2016, Zendaya is giving us a youthful, fun moment that is neverless incredibly chic and put-together.

At the Critics' Choice Awards, 2020

This is literally a pink breastplate, yet somehow...it's just effortless and cool on the starlet! The Tom Ford outfit was from the brand’s spring 2020 collection. As she told Entertainment Tonight, "I saw it on the runway and thought it was sick and amazing because they were actually able to scan and mold my own body so it fits me the right way, so it’s pretty cool...It was a very science-tech situation going on, so it was very [one-of-a-kind]."

At the Premiere of 'Spider-Man Far From Home,' 2019

Get it? Because the Spider-Man costume is black and red?? Roach wrote on Instagram, "[If] she was Spider-Man, this would be her suit.” Even when she's committing to a particular theme and color scheme, Zendaya manages to give it a couture-cool spin. The sequinned Armani Privé dress was also backless, which, combined with the side cutouts, is a daring look—yet still comes off as easy-breezy for the actor.

At the Met Gala, 2016

I mean...who else can pull off this haircut?? For the "Manus x Machina: Fashion In An Age Of Technology" Met Gala, Zendaya wore a bronze Michael Kors Collection gown and a...bowl mushroom hairdo! She drew comparisons to Liza Minnelli, who has graced us previously with a similar haircut, and if we're using an icon like that as inspiration, we're doing pretty well for ourselves. This was only her second Met Gala, but wow did she nail it.

At the Premiere of 'Confirmation,' 2016

I admit that maybe not everyone loves this dress as much as I do (the dress kind of looks like the paint swatches you might get when you're trying to decide on a color?), but I don't care, because it's both a gorgeous pattern and a dress that she's working to the absolute max. FYI, this is from the Rani Zakhem Spring 2016 collection, and she's absolutely wearing it instead of the other way around. I even love the matching pink shoes!

At the "Dune" Photocall at Le Grand Rex, 2021

Zendaya really breaks out her coolest, most architectural fashion for Dune events. This purple two-piece was designed by Alaïa's creative director Pieter Mulier for their Spring/Summer 2022 collection; Law Roach called her a "grown woman" (with video of the star set to Beyoncé's "Grown Woman," obviously). Fluffy on the top (look at that gorgeous hair!) and bottom, fitted through the body, it's one of those "only Zendaya could do this" outfits.

At the Australian Premiere of 'The Greatest Showman,' 2017

This is the greatest show! (Just a little Greatest Showman humor for you!) This butterfly-inspired gown is Moschino by Jeremy Scott—and again, it's thematic, since her character literally flies through the air in the movie, and also because her career was taking off at this moment. She wisely styled this standout gown with super-simple accessories and curled old-Hollywood hair, because (obviously) all eyes should be on the dress.

At the Golden Globes After Party, 2016

This rich Marchesa gown was perfect for a red carpet, but (since she was headed to a party), it also had a cool design feature: You can "pin" the bottom tiers of the dress so that the dress goes from full-length to midi!! "I can't take much credit for the transition from long to short," Law explained of the dress. "It was one part great construction from Marchesa and the other Zendaya hiking up her dress ready to dance the night away.”

At the Launch of the Nita Mukesh Ambani Cultural Centre (NMACC), 2023

This sparkling purple sari is both thematic to the event (Zendaya, Tom Holland, and Roach were there to celebrate the opening of the Nita Mukesh Ambani Cultural Centre (NMACC)) and also absolutely one of the best things she's ever worn. The Rahul Mishra outfit had a gold sparkly bralette, a full skirt with stars, flowers, and animals on it, and a sheer train. Oh, and Bulgari jewels to complete the look. Of course.

At the Ralph and Russo Afterparty, 2017

Drawing comparisons to Audrey Hepburn (and with good reason) this Ralph & Russo gown has a partially-attached, contrasting navy blue train that peeks out ever-so-glamorously around her dress. Earlier, she attended the show in a very work-appropriate white peplum top and skirt from the spring 2017 couture collection, combined with Chopard jewels, but this is a gown and absolutely appropriate for a more formal setting.

At the 2022 HBO Emmys Party

Red plunging Valentino? No problem!! Pairing this with Bulgari jewels, the whole outfit pairs exceedingly well with her best accessory ever (the Emmy she won, naturally). This was the second outfit of the night, after her big black Valentino ballgown that was crafted in a week after it came to her in a dream. I would argue this one's even cooler—even though it's an embarrassment of riches—but it makes sense given how much she looks like a winner.

At a 'Dune' UK Screening, 2021

It's no wonder W Magazine called her a "sci-fi princess" in this look: It's architectural, it's cool, it actually looks very comfortable yet sacrifices exactly none of the style. This Rick Owens gown is exactly right for a Dune screening (it semi-matches the types of outfits her character would wear), except made red carpet-ready in a multitude of sequins. It's hard to see from this angle, but it's only got one sleeve on top of that cute little train!

At the 'Bulgari Mediterranea High Jewelry' Event, 2023

Now that is a black ballgown. This Richard Quinn ensemble is making her look like the most chic mermaid of all time; Zendaya wears Bulgari all the time and is, unsurprisingly, one of their ambassadors. I didn't know "summer velvet" could be a thing, but she's making it look effortless. And, of course, she's wearing Bulgari jewels, including that absolutely show-stopping snake necklace that is undoubtedly highly expensive.

At the Met Gala, 2017

For the "Rei Kawakubo/Comme des Garcons: Art Of The In-Between" Met Gala, Zendaya wasn't exactly on the avant-garde theme in this Dolce & Gabbana Alta Moda ball gown parrot print dress. But honestly, who cares? A gorgeous Afro and coral lip were the perfect maximalist touches to go with a big, voluminous, gorgeous-in-every-way outfit. Rihanna called her a "brown goddess," which is the RiRi stamp of approval.

At the 2018 Met Gala

For the "Heavenly Bodies: Fashion & The Catholic Imagination" themed Met Gala, Zendaya pulled out all the stops, and absolutely nailed it. This might not be everyone's favorite gown of hers—but I think it's the coolest, most audacious outfit. I mean, she's wearing a feminized suit of armor! It's custom Atelier Versace, and a nod to Joan of Arc. She told InStyle it was one of her favorite looks ever, because she felt like "nothing could hurt me—I was like a warrior." Iconic.