Top 10 Avant-Garde Red Carpet Looks of All Time

Welcome to MsMojo, and today we’re counting down our picks for the wildest, campiest, and most creative looks to ever hit the red carpet.

#10: Rihanna & A$AP Rocky

“Met Gala” (2021)

With several Met Galas under their belts, it’s hard to choose a favorite avant-garde look from Rihanna and A$AP Rocky. At 2017’s “Rei Kawakubo/Comme des Garçons: Art of the In-Between” theme, Riri went solo and wowed in a punk rock floral creation. In 2023, she wore an all-white Valentino gown with large roses and did a mid-carpet wardrobe change, while her partner rocked a Gucci ensemble with a red kilt over embellished denim. But we have to highlight the stylish power couple’s first Met Gala together in 2021. Rihanna wore a custom Balenciaga sculptural comforter-like gown and A$AP Rocky looked just as cozy in a multicolor quilted cape by ERL. These bold trendsetters love to experiment with fashion, and they never miss.

#9: Cynthia Erivo

Mexico City Premiere of “Wicked” (2024)

If Cynthia Erivo wasn’t already considered a style icon, her “Wicked” press tour surely would’ve earned her the title. At the 2024 Mexico City premiere, she stepped out in a custom Thom Browne dress with a corset bodice and floor-length structured skirt. Erivo is known for her avant-garde nail art that elevates every look, and she also got a mani for the sculptured witch hands on the shoulders. Months later, the Best Actress nominee dominated the Oscars red carpet in a custom Louis Vuitton deep emerald velvet ballgown with a high collar and dramatic off-the-shoulder sleeves shaped like a giant bow. Erivo is always like a walking piece of art, and both looks are excellent examples of her unique approach to fashion.

#8: Celine Dion

“71st Academy Awards” (1999)

These days, we’re used to seeing women rock menswear both on and off the red carpet. But at the “71st Annual Academy Awards” in 1999, Celine Dion’s pants suit caused a stir. The Best Original Song nominee hit the Oscars red carpet in an all-white tuxedo from John Galliano’s Spring 1999 couture collection for Christian Dior. She turned heads not only for going against societal norms by wearing pants when women were expected to wear gowns, but also for the back-to-front tuxedo jacket and daring low-back design. Dion topped it off with a matching white fedora cocked to the side and black diamond-studded Ray-Bans. It’s a look that confused some and delighted others, and is now considered a trailblazing fashion moment.

#7: Cher

“58th Academy Awards” (1986)

When people hear the term “revenge dress,” they think it’s likely the result of a breakup. But at the “58th Academy Awards,” Cher served her own vengeance-inspired look after she was snubbed for her work in “Mask.” The Bob Mackie-designed two-piece ensemble featured a jewel-encrusted, bra halter top and a long skirt with two side slits that hung low on the waist. Cher wanted to make a statement, and the midriff-baring outfit certainly did, along with the showgirl-esque feathered headpiece. Two years later, the icon brought her wild, rule-breaking style to the Oscars red carpet in another sheer Bob Mackie gown, and this time, she took home the gold.

#6: Janelle Monáe

“Met Gala” (2025)

Multi-talented Janelle Monáe is known for their eccentric style, and the Met Gala is definitely where their fashion thrives. At the 2025 Met Gala, the artist nailed the year’s theme, “Superfine: Tailoring Black Style,” wearing a custom half-black and half-pinstripe tailored suit designed by Thom Browne and Broadway costume designer Paul Tazewell. A boxy, red-and-white-striped design, along with the gold detailing, made the suit pop even more. Monáe was a walking optical illusion, and beneath was a deconstructed part-suit, part-gown design in the same black, white, and red palette. Monáe topped off the surreal look with a black-and-white bowler hat with a ticking monocle clock attached. They wanted to serve “Time-Traveling Dandy,” and more than delivered.

#5: Lizzy Gardiner

“67th Academy Awards” (1995)

Award-winning costume designer Lizzy Gardiner turned heads at the 1995 Academy Awards wearing a dress made of 254 expired American Express Gold cards, with a matching shawl and platform heels. The eye-catching look almost made an appearance in “The Adventures of Priscilla, Queen of the Desert,” the cult classic for which she was nominated and won. Since AmEx wouldn’t approve it for the film, she decided to wear it herself. If anyone was unfamiliar with Gardiner or her work, they surely knew who she was after seeing the campy creation. At the time, some critics considered it a top pick for one of the worst Oscar gowns ever. Decades later, the look is so iconic that it has its own Wikipedia page.

#4: Zendaya

London Premiere of “Dune: Part Two” (2024)

For years, Zendaya has been slaying red carpets in looks ranging from classic and chic to sexy and daring. Her boldest looks have typically appeared at the Met Gala, like the Joan of Arc-inspired Atelier Versace chainmail gown she wore for 2018’s “Heavenly Bodies: Fashion & The Catholic Imagination.” And we also must mention her custom Maison Margiela by John Galliano emerald and navy dress with flora-and-fauna motifs in 2024. But at the 2024 “Dune: Part Two” premiere in London, the actress went full avant-garde in vintage Thierry Mugler. The futuristic “Metropolis”-esque articulated metal catsuit comes from the designer’s Fall/Winter 1995 Couture collection and is hands down one of Zendaya’s most audacious looks to date.

#3: Grace Jones

“25th Grammy Awards” (1983)

When it comes to unconventional fashion, the legendary Grace Jones was a pioneer in androgynous style and fearless self-expression. One of her most memorable looks was at the 25th Grammy Awards, where she graced the red carpet in a sculptural leather ensemble, featuring a rattan and bamboo top with a matching ultra-wide-brim, umbrella-shaped hat from Issey Miyake’s Spring/Summer 1982 collection. The multi-hyphenate artist was one of Miyake’s muses, a match made in haute couture heaven. Jones is often called the embodiment of avant-garde, especially when she wears pieces from this designer, and we wholeheartedly agree.

#2: Lady Gaga

“27th MTV Video Music Awards” (2010)

Known for her extravagant style, Lady Gaga owns every red carpet she’s graced. At the 2010 Grammy Awards, she was a literal star, turning heads in a custom Armani Prive galaxy gown and carrying a silver starburst. In 2019, she unsurprisingly nailed the “Camp: Notes on Fashion” theme at the Met Gala and dominated the carpet, serving not one but four different black-and-hot pink looks designed by Brandon Maxwell. But who could forget Mother Monster’s infamous meat dress at the 2010 MTV Video Music Awards? Designer Franc Fernandez draped Gaga in head-to-toe raw flank steak, crafted into an asymmetrical silhouette. While reactions were divisive, the look will go down in pop culture history as one of the wildest fashion moments.

Before we unveil our top pick, here are a few honorable mentions.

Barbra Streisand, “41st Academy Awards” (1969)

The Actress-Singer Nabbed an Oscar Wearing an Arnold Scaasi Sheer Pantsuit

Sarah Jessica Parker, “Met Gala” (2006)

The Style Icon Donned a Deconstructed Tartan & Tull Alexander McQueen Creation

Billy Porter, “91st Academy Awards” (2019)

The “Pose” Star Collaborated with Christian Siriano on This Black Velvet Tuxedo Gown

Tyla, “Met Gala”(2024)

The Singer-Songwriter Wore a Sands of Time-inspired Balmain Gown to the Met Gala

Jared Leto, “Met Gala” (2019)

The Actor-Musician Wore a Red Gucci Gown with His Own Head as an Accessory

#1: Björk

“73rd Academy Awards” (2001)

In 2001, Björk attended the Academy Awards as a Best Original Song nominee. While the Icelandic singer-songwriter didn’t take home the statue, she made a big splash on the red carpet wearing her now iconic swan dress designed by Marjan Pejoski. With all the unconventional outfits we see today, Björk’s swan dress and pretend egg-laying on the red carpet aren’t that shocking. But at the time, people were far from ready to appreciate the artistry. It was parodied to death, but has since been honored, even displayed in the Metropolitan Museum of Art’s “Camp: Notes on Fashion” exhibit. And there’s no doubt we’ll still be talking about it decades from now.

What avant-garde look do you think is the most iconic? Let us know in the comments below.