The Most Daring Outfits to Ever Hit the Red Carpet

The best season of the year is Awards Season, and that's a fact. (Thank you, Moira Rose, for reminding the world of this.) Every year, we gather in front of our phones and our computers to devour and dissect our favorite celebrity's fashion moments. It's the best type of sport, and even better, it shows us how daring and innovative fashion can be. Here, we gathered 32 of the most daring red carpet looks ever, from Björk's swan dress to Jared Leto's beheaded twin at the Met Gala.

Kylie Jenner

Kylie Jenner lit up the 2019 Met Gala in a lavender Versace gown with feathered accents and a sheer bodice. The dramatic train and bold color made her one of the night’s most unforgettable fashion moments, perfectly embodying the night's theme of Camp: Notes on Fashion, because it's almost impossible to describe, but you get it when you see it.

Doja Cat

Doja Cat took her name a little too literally and the night's theme a bit too literally when she embraced her feline side at the 2023 Met Gala. The evening's theme, Karl Lagerfeld: A Line of Beauty, asked guests to "dress in honor of Karl"—so Doja Cat said, "bet," and transformed herself into a life-size cat inspired by Karl Lagerfeld’s beloved pet, Choupette. With prosthetic makeup and a glittering gown, she combined humor and high fashion in one unforgettable look.

Megan Fox

Megan Fox made jaws drop at the 2021 VMAs in a completely sheer Mugler gown. With her wet-styled hair and an embellished thong, she redefined the naked dress, exuding confidence and modern glamour in equal measure. It was so risqué, but given the history of the MTV Video Music Awards, it was probably the classiest naked dress we've ever seen on that red carpet.

Erykah Badu

No one does "daring" quite like Erykah Badu. Erykah Badu brought drama to the 2014 Soul Train Awards in a towering white top hat, complete with an gold triangular sculpture and a white fur coat with matching over the top sleeves. Her unique approach to fashion has been nothing short of iconic, proving she’s always in a league of her own.

Emily Ratajkowski

Emily Ratajkowski channeled Cher-inspired glam at the 2019 Met Gala in a Dundas gown with daring cutouts and a bejeweled headpiece. The sultry design fit perfectly with the camp theme, turning heads all night. She had to have a lot of faith in her double-sided tape, because if that headpiece fell off, we could have had a true wardrobe malfunction.

Miley Cyrus

Miley Cyrus brought edge to the 2020 VMAs in a see-through Mugler dress. With its mesh panels and metallic accents paired with a black panty and bandeau top to keep her modest, the look was a nod to her rockstar persona, proving Miley knows how to dominate any stage or red carpet. The mullet and red lipstick really make this a truly stellar look.

Beyoncé

Beyoncé dazzled at the 2015 Met Gala in a sheer, jewel-encrusted Givenchy gown. In true diva form, Beyoncé arrived late, being the last to walk the red carpet—but the wait was absolutely worth it. The intricate embellishments and daring silhouette showcased her confidence, but we also love a rare Beyoncé red carpet moment because she always serves glamour with a bold, seductive twist.

Billy Porter

Billy Porter redefined everyone's idea of what red carpet fashion is when he appeared at the 2019 Oscars in a Christian Siriano tuxedo gown. Yes, you read that right: A tuxedo...gown. By merging masculine and feminine aesthetics, the look shattered conventions, sparked conversation about gender in fashion all over the world, and created a groundbreaking moment in fashion history. Porter would continue to serve lewks on the red carpet forever.

Janelle Monaé

Janelle Monáe is never going to give you just a conventional Oscars gown. At the 2020 Academy Awards, she dazzled in a Ralph Lauren gown covered in over 168,000 Swarovski crystals. The hooded design combined futuristic glamour with a timeless and classic silhouette, making her a standout on the Oscars red carpet, but feels entirely rooted in her identity.

Jared Leto

Jared Leto made waves at the 2019 Met Gala by carrying a replica of his own head as an accessory. Paired with a red jeweled Gucci silk suit, the look fully embodied the night’s “Camp” theme and had everyone losing their minds (and heads) over the concept. It was the perfect blend of creepy and classic, exactly what we want from a Met Gala red carpet.

Bella Hadid

Bella Hadid stole the show in 2021 at the Cannes Film Festival, where she appeared in a Schiaparelli gown featuring a gilded lung-shaped necklace that covered her bare chest. Schiaparelli is known for their avant-garde design, and Hadid is the perfect person to wear a daring design like this, blurring the line between couture and art.

Lizzy Gardiner

Costume designer Lizzy Gardiner turned the 1995 Oscars into a runway for innovation with her American Express gold card dress. The gown, made entirely of 254 expired credit cards, and paired with matching gold shoes was a bold, creative statement that still has people talking decades later. Gardiner won the Academy Award for Best Costume Design for her work on The Adventures of Priscilla, Queen of the Desert that evening, but this design was career-defining.

Cher

This list would be incomplete if we didn't mention Cher’s legendary Bob Mackie gown at the Oscars. With its sheer fabric, feathered headdress, and bold embellishments, the "loin cloth" dress remains one of the most daring and memorable red carpet appearances of all time. The most notorious detail is that the outfit was a collaborative design between Cher and Mackie, rooted in the fact that she didn't feel taken seriously an an actress by the Academy, and wanted to make a point. “Because I didn’t get nominated for a movie that everyone thought I would actually win [Mask], but I didn’t get nominated, and they thought I wasn’t serious," Cher explained in the documentary Bob Mackie: Naked Illusion.

Heidi Klum

In one of the most unrecognizable appearances she's ever made, supermodel Heidi Klum took her annual Halloween party costume to an even more absurd level in n 2022, transforming into a giant, hyper-realistic earthworm. Known for her elaborate costumes, this bizarre yet creative look showcased her dedication to making every Halloween unforgettable. (Just don't zoom in too far, it's a jumpscare.)

Lady Gaga

Lady Gaga’s Met Gala entrance in 2019 was a performance in itself, with four bold outfit reveals by Brandon Maxwell. As a co-char for the camp-themed Met Gala, the singer launched the evening's red carpet in a magenta pink cape gown that felt like the chicest parachute you've ever seen, being guided by six dancers in tuxedoes, all holding black umbrellas. The dancers removed the cape to show a black gown underneath at the end of the stairs, and Gaga makes her way to the top of the staircase again, so Maxwell can remove the black gown to show a darling magenta pink satin gown, complete with a '90s bedazzled cell phone and enormous cat eye sunglasses. But that's not all: Once she's done doing Businessy Business on her phone call, she strips to black sparkling lingerie, 10-inch platform boots, and a pair of fishnets. Each layer celebrated camp and Gaga’s unapologetic love for drama.

Carmen Electra

In the '90s, Carmen Electra defined a daring red carpet moment. Here, Electra turned heads at the 1997 MTV VMAs in a black floor-length dress that took a side split to a new extreme and showed every curve. The bold design, complete with chain-like embellishments, proved that she was never afraid to push boundaries and steal the spotlight.

Kim Kardashian

Kim Kardashian was truly unrecognizable in this full-body Balenciaga look at the 2021 Met Gala. It's easy to call this daring — it was a masterclass in minimalism and mystery. Covering her from head to toe in black fabric, the look blurred identity and sparked endless conversations about fashion as art. She walked the carpet with luxury label’s creative director, Demna Gvasalia, who was also shrouded in a similar blackout look.

Cardi B

Cardi B turned heads in an archival Mugler “Venus” gown—a true masterpiece. The dramatic sculptural skirt, the pearl accents, and old-Hollywood allure made her look like a living statue of Aphrodite, redefining red carpet elegance with a bold avant-garde edge. It was one of Cardi's softer looks, juxtaposing the grit of her raps.

Solange

Solange brought avant-garde drama to the 2015 Met Gala in a sculptural Giles dress. The swirling pattern and over-exaggerated, blobby silhouette made her a walking piece of modern art, proving she’s always a fashion trailblazer. It's the best game of peek-a-boo we've ever played.

Zendaya

Zendaya’s sculptural Mugler bodysuit for a Dune: Part Two premiere was the robot suit of our fashion dreams. The futuristic design, with intricate cutouts and flowing fabrics, was pulled by Zendaya and long-time stylist Law Roach from 1995 Thierry Mugler archives, and a hope that they could get her to fit in the outfit—it wasn't designed to be actually worn by anyone. But they got lucky: Zendaya shared in a video for Vogue: “One of the men who originally made it was with us and he was like, ‘You know, we can try it, but there's also a world where certain parts won't fit,’” she finished. “We tried it on, It fit like a glove, and I was like, ‘This is so crazy.’ And everybody was like, ‘Oh!’ It just felt very meant to be.”

Irina Shayk

Irina Shayk made a daring statement at the 2015 Vanity Fair Oscars Party in a sheer, body-hugging Atelier Versace gown. With bold cutouts and shimmering details, the look was unapologetically glamorous and daring—the mesh cutouts leave absolutely nothing to the imagination in the very best way.

Kendall Jenner

Kendall Jenner’s crystal-covered La Perla gown at the 2017 Met Gala left little to the imagination. With a thigh-high slit, glittering mesh, and a daring cut through her abdomen, she confidently embraced the night’s “Rei Kawakubo/Comme des Garçons” theme, proving less can indeed be more.

Ciara

Ciara was a vision of daring elegance at the 2016 Grammys. Her Alexandre Vauthier gown, featuring a dramatic slit and bold asymmetry, walked the perfect line between revealing and refined, making her a standout on music’s biggest night. Loosen up her buttons? I don't see any buttons to be loosened, there's barely any fabric!

Kim Kardashian

Kim Kardashian stunned at the 2019 Hollywood Beauty Awards in a vintage Thierry Mugler gown from the designer's Spring/Summer '98 collection. The vampy black body-hugging design left absolutely nothing to the imagination courtesy of strategic cut-outs and a thigh-high slit, making it one of her most daring red carpet looks, of which Kardashian has many.

Doja Cat

As double-duty host and performer (and winner!) at the 2021 MTV Video Music Awards, Doja Cat put on a true fashion parade with six extremely different looks throughout the evening. In a night where she rocked avant-garde styles, including a literal chair hat by Vivienne Westwood, this Gustav Klimt-inspired hooded gown from Thom Browne's 2018 Spring/Summer ready-to-wear collection will always stand out as one of her most daring looks.

Gwyneth Paltrow

Gwyneth Paltrow took a gothic turn at the 2002 Oscars in a sheer Alexander McQueen gown. The edgy bodice comprised of a sheer mesh sleeveless bra-free top, rumpled skirt and dramatic eyeliner were polarizing at the time. Paltrow even admitted to making a fashion faux pas in a QA post on Goop in 2013: "There were a few issues; I still love the dress itself but I should have worn a bra and I should have just had simple beachy hair and less makeup," she wrote. "Then, it would have worked as I wanted it to — a little bit of punk at the Oscars."

Nicki Minaj

Nicki Minaj roared onto the 2011 Grammys red carpet in a head-to-toe leopard Givenchy look. It's like if Cruella De Ville wanted leopards instead of Dalmatians. From the dramatic Bride of Frankenstein wig to the fierce gown, she turned a wild print into a high-fashion moment only she could pull off. It may have not been a hit with fashion critics, but it solidified Minaj's place as someone who isn't afraid of a risk.

Rihanna

Rihanna’s Swarovski-crystal-encrusted gown at the 2014 CFDA Awards was unapologetically bold. The sheer backless and bra-less dress, paired with a matching durag headscarf and fur stole, showcased her fearless approach to fashion and solidified her as an undeniable style icon. She took Old Hollywood into the modern age, and then sent it right back—it's one of her best looks ever.

Christina Aguilera

There are some iconic MTV Video Music Awards looks, and this one from the 2002 VMAs from Christina Aguilera is absolutely one of them. A look that would define fashion for an era, Aguilera turned heads at the 2002 VMAs in a barely-there scarf top, white pageboy top, and a denim micro-mini skirt. She would later present an award to her then-rival, Eminem, and her delivery of "Interesting, Eminem," cemented this look and that award as one of the best moments in the award show's history.

Jennifer Lopez

There are rare moments where fashion creates technological innovation, but this iconic Versace look from Jennifer Lopez changed the internet forever. Lopez' Versace dress rewrote fashion history: The daringly plunging neckline and bold tropical print became so iconic, it inspired the invention of Google Images. J.Lo didn’t just wear a dress; she created a moment.

Toni Braxton

Toni Braxton’s white Richard Tyler gown at the 2001 Grammys was the epitome of bold minimalism. The white floor-length gown featured cut-outs and dangerously high slit turned heads, showing that simplicity and risk can go hand-in-hand on the red carpet.

Björk

Come on, it's Björk’s swan dress. We all know it, we all love it. This dress has to be one of the most unforgettable moments in Oscars history, leading to dozens of parodies and attempts at recreation. The avant-garde Marjan Pejoski creation, complete with a faux bird wrapped around her, blurred the lines between costume and couture. Love it or hate it, it was pure Björk.