All of Olivia Rodrigo's most daring looks

Olivia in a black long sleeve minidress with a large lime green bow across her chest and a black mesh neckline and sleeves. She's wearing black sheer knee-high socks and platform boot heels.
Olivia Rodrigo attending Variety's Hitmakers Brunch on December 4, 2021.Matt Winkelmeyer/Getty Images
  • Olivia Rodrigo won three Grammy awards on Sunday — it was the first year she was nominated.

  • The singer wore a black Vivienne Westwood gown with a sparkling body silhouette on it.

  • She is already a fashion icon, wearing many iconic looks since releasing "Drivers License" in 2021.

Olivia Rodrigo wore a bold fluorescent-green Dior dress to her first major award show: the 2021 Brit Awards.

Olivia in a neon green/yellow strapless dress with a full tulle skirt that ends at her ankles. She has a black belt and black platform heels.
Olivia Rodrigo attending the Brit Awards on May 11, 2021.Dave J Hogan/Getty Images

In May 2021, four months after releasing her hit song "Drivers License," Olivia Rodrigo started wearing a string of iconic and daring looks. At the 2021 Brit Awards, the singer wore a custom neon-green Dior Haute Couture tulle ankle-length dress on the red carpet. Paired with black accessories, the look was a mix of hard and soft.

"The timeless silhouette in such a vibrant color felt so youthful and joyful, with a nod to Olivia's upcoming debut album, 'Sour,'" Rodrigo's stylist Anna Hughes-Chamberlain told British Vogue.

Later in the night, she performed in a sheer red dress with a sequin set showing through.

Olivia in a red sheet cape dress overlaying a red sequin miniskirt.
Olivia Rodrigo performing "driver's license" at the Brit Awards on May 11, 2021.JMEnternational/Getty Images

Rodrigo performed "Drivers License" at the 2021 Brits in a second custom Dior look. Her costume had a sheer red cape dress over a sequined bra top and miniskirt. Rodrigo's stylist told British Vogue that red was the perfect color to play off the song's line, "Red lights, stop signs."

Rodrigo added, "Performing live at the Brits was such an amazing moment for me and to do that wearing custom Dior was incredible."

Rodrigo wore a sophisticated Chanel skirt suit and youthful heels to meet President Joe Biden.

Olivia in a pink plaid jacket and matching mini skirt. She's holding a black mini purse, wearing black tall socks and tall cream platform heels.
Olivia Rodrigo on her way to meet President Joe Biden at the White House on July 14, 2021.Chip Somodevilla/Getty Images

One of the most influential Gen-Z figures, Rodrigo was asked to meet with President Joe Biden and Dr. Anthony Fauci in July 2021 to spread awareness about children getting vaccinated.

Rodrigo opted to wear a preppy vintage Chanel skirt suit that was very Jackie Kennedy-esque. This look may not seem particularly daring, apart from the Giuseppe Zanotti platform booties, but when you realize Rodrigo wore the wool set on a 91-degree day, it amps up the drama.

Contrary to popular belief, though, wool can actually be cooling depending on its weight and construction, as Insider previously reported.

The singer also put on a pair of Biden's signature aviator sunglasses with him for a fun Instagram post.

The singer stunned in a bright sherbert and pink gown to attend the MTV VMAs in September 2021.

Oliva posing to show the back of her dress. A sherbert orange strapless floor-length mermaid dress shows a back corset surrounded by dark pink tulle.
Olivia Rodrigo attending the MTV Video Music Awards on September 12, 2021.Jason Kempin/Getty Images

At Rodrigo's first MTV VMAs, she was nominated for five awards. She wore a sherbert-orange and hot-pink Atelier Versace gown.

It had an exposed corset in the back and tulle draped over the gown. Rodrigo also wore dangling butterfly earrings, nodding to the imagery of butterflies in her album art and music videos.

On defining her style, in an August 2021 GQ interview, Rodrigo said, "I've been working on sets for so long, where you go and you're told what to say and told what to wear." She added, "The fact that when you're making a music video or something, people just come up to you and they're like, 'What do you want to make to [wear for] the song that you wrote?' [...] That's the coolest thing ever."

Rodrigo won three Moonmen awards that night, accepting two in this gown.

During the VMAs, she wore a tiered minidress with delicate gloves and hard black boots.

Olivia in a purple and baby plue strapless minidress with a a tiered skirt. She has purple gloves, flowers in her hair, sheer black tights, and chunky black boots on.
Olivia Rodrigo accepting the song of the year Moonman award after performing "good 4 u" at the MTV Video Music Awards on September 12, 2021.Kevin Mazur/MTV VMAs 2021/Getty Images

For her very naughts-inspired style and performance of "Good 4 U" at the VMAs, Rodrigo wore a light-purple and baby-blue minidress with a tiered skirt from the Heaven collection by Marc Jacobs. It was styled with purple satin gloves, a black bralette, sheer black tights, and Doc Marten boots.

For her first performance since the release of her album "Sour" in May 2021, Rodrigo kept on theme and had metallic butterfly clips in her hair.

She also wore the look to accept her song of the year award for "Drivers License."

In September, for her first Met Gala, Olivia Rodrigo channeled old Hollywood glamour in YSL.

Olivia in a black lace catsuit with a large black feather off the shoulder shall and black high-waisted underwear showing underneath the lace. She's wearing black platform heels.
Olivia Rodrigo attending the Met Gala on September 13, 2021.Arturo Holmes/MG21/Getty Images

The 2021 Met Gala's theme was "In America: A Lexicon of Fashion." Rodrigo attended the event for the first time wearing an Yves Saint Laurent lace catsuit. The sheer material revealed high-waisted black underwear underneath, and the off-the-shoulder feather boa punctuated the look with extra drama.

It was styled with dangling earrings and platform heels. While not created by an American designer, the look was a modern take on old Hollywood glamour.

Speaking to Keke Palmer during Vogue's red-carpet coverage, Rodrigo explained her fashion choice, saying, "I personally love American punk music, and I think Saint Laurent does a really good job of making punk rock feminine. So that's what I was going for tonight," as per Billboard.

She had a unique plunging neckline on her gown for an Academy Museum of Motion Pictures gala.

Olivia in a black strapless gown with a dramatic curving neckline that shows off her cleavage and swoops to her upper abdomen. She has a leg slit and is wearing black strappy heels.
Olivia Rodrigo attending the Opening Gala at the Academy Museum of Motion Pictures on September 30, 2021.Amy Sussman/Getty Images

Also in September, the singer attended the opening gala for the Academy Museum of Motion Pictures in her most revealing look yet. This elegant gown was her second daring Yves Saint Laurent dress.

Looking like a femme fatale, Rodrigo's dress featured a curved plunging neckline and a high leg slit that showed off the singer's black strappy heels.

A shorter version of the dress was previously worn by Hailey Bieber and by the character Camille in the second season of "Emily in Paris" before Rodrigo wore it.

Rodrigo cemented her place in the fashion world with a shimmering periwinkle dress at the 2021 VMAs.

Olivia in a sequin and sheer periwinkle dress with a v-neck. You can see high-waisted underwear underneath. The bottom of the dress has a thick purple feather trim. She's wearing metallic strappy heels.
Olivia Rodrigo attending the 2021 American Music Awards on November 21, 2021.Amy Sussman/Getty Images

Rodrigo packed a punch in her 2021 AMAs look in November 2021. It had everything from a bright color and sequins to a sheer material and feather trim to a plunging neckline and exposed undergarments.

The periwinkle David Koma dress shimmered on Rodrigo and helped her stand out from other attendees. She paired it with metallic strappy heels.

That night, Rodrigo accepted the new artist of the year award in this dress and performed her song "Traitor."

An oversized bow was the highlight of her look at Variety's Hitmakers Brunch in December 2021.

Olivia in a black long sleeve minidress with a large lime green bow across her chest and a black mesh neckline and sleeves. She's wearing black sheer knee-high socks and platform boot heels.
Olivia Rodrigo attending Variety's Hitmakers Brunch on December 4, 2021.Matt Winkelmeyer/Getty Images

Olivia Rodrigo proved that she's a trailblazer in music and in fashion at Variety's 2021 Hitmakers Brunch. To be honored as the songwriter of the year, Rodrigo wore a fun Calvin Luo spaghetti-strap minidress with an oversized pistachio-green bow across her chest.

The singer styled it with a mesh long-sleeve shirt underneath, sheer black knee-high socks, and velvet Mary Jane platforms by Nodaleto.

Glamour and grunge blended in this mirrored dress at the 2022 Brit Awards.

Olivia posing to show her profile. Her silver dress with a cowl neckline and low back is covered in shimmering mirrored scales.
Olivia Rodrigo attending the BRIT Awards on February 8, 2022.Mike Marsland/Getty Images

Rodrigo often expertly balances on a fine line between glamour and grunge. She achieved this again in a silver slinky dress at the 2022 Brit Awards in February. The flowing Alexandre Vauthier gown had a cowl neckline and an exposed back. The fishtail dress sparkled from every angle with diamond-shaped sequins that had a mirror effect.

Up against 13 other artists, Rodrigo won the award for best international song of the year for "Good 4 U."

She wore a witchy Winona Ryder-esque look for a Billboard after-party.

Iris in a black spaghetti strap mini dress and bright pink tights. Olivia in a black crotchet spiderweb-like off-the-shoulder long sleeve dress with garter leg straps. She's wearing black knee-high platform boots.
Iris Apatow (left) and Olivia Rodrigo (right) attending a Billboard Women in Music Awards after party on March 2, 2022.Neil Mockford/Ricky Vigil M/Getty Images

In March, after winning Billboard's Women in Music Awards' coveted women of the year award in a white Area dress with black platform boots, Rodrigo went to celebrate her achievement at an after-party with her best friend, Iris Apatow.

The singer kept on her boots but changed into a web-like crochet off-the-shoulder dress. The sultry look with leg garter straps gave Rodrigo a witchy appearance.

"I love Winona Ryder — she's my favorite ever," Rodrigo previously told GQ about her fashion inspiration. "I've watched all her movies and look at all of her style references and stuff like that."

For a fun interview with James Corden, Rodrigo wore an equally fun and colorful tweed and feather minidress.

Olivia Rodrigo backstage of "The Late Late Show with James Corden" on Tuesday, March 22, 2022.
Olivia Rodrigo backstage of "The Late Late Show with James Corden."Terence Patrick/CBS via Getty Images

Rodrigo is unafraid of color or playing with prints and textures. In an interview on "The Late Late Show with James Corden" in March, Rodrigo mixed all three, wearing a baby-blue and pink houndstooth tweed minidress with feather straps.

The vibrant Area dress was whimsical and youthful. She styled it with her signature sheer black tights and platform heels.

After filming the show during the day, she attended the iHeartRadio Music Awards at night in another daring look.

Her purple bustier dress and latex leggings formed a structured and shiny look for the iHeartRadio Music Awards.

Olivia in a bright purple strapless minidress with boning. She has black latex tights on and pointed black heels. She's holding three awards.
Olivia Rodrigo posing with her three awards at the iHeartRadio Music Awards on March 22, 2022.Steve Granitz/Getty Images

The singer wore a daring off-the-runway Versace ensemble to attend the 2022 iHeartRadio Music Awards, where she was nominated in many categories. Her violet structured bustier minidress was paired with latex leggings and pointed platform booties.

She wore the sleek and sultry look to pick up her awards for female artist of the year, best new pop artist, and TikTok bop of the year for "Good 4 U."

The singer wore a dramatic and romantic ensemble for the March premiere of her documentary, "Olivia Rodrigo: Driving Home 2 U."

Olivia in a black corset with pink bows and a pink miniskirt. She's wearing black gloves with matching pink bows, black sheet knee high socks and black platform heels.
Olivia Rodrigo attending her movie premiere for her Disney+ documentary "Driving Home 2 U" on March 24, 2022.Tommaso Boddi/Getty Images

For the Los Angeles premiere of her Disney+ documentary, "Olivia Rodrigo: Driving Home 2 U," the singer showed out in a black corset and pink miniskirt. The Fancí ensemble included a bow-adorned corset with matching opera-style gloves and skirt.

The modern coquette-inspired look was paired with black knee-high sheer socks and GCDS platform heels.

Rodrigo's documentary was released for all to see on March 25, 2022.

Wearing custom Vivienne Westwood, Rodrigo stole the show in this optical-illusion dress at the 2022 Grammys.

Olivia in a black off-the-shoulder satin gown showing off her cleavage. The dress has a faux outline of breasts and a silhouette of a body in pink sparkles. She's wearing black off the elbow gloves and two choker necklaces.
Olivia Rodrigo attending the 64th Annual Grammy Awards on April 3, 2022.Frazer Harrison/Getty Images

Walking into her first Grammys with seven nominations, Olivia Rodrigo didn't come to play with her accomplishments or her outfit.

The singer graced the red carpet in a custom Vivienne Westwood Couture black satin gown. Clusters of pink crystals created an outline of an hourglass silhouette on the front and back of the dress. She styled it with two '90s choker necklaces and opera-style satin gloves.

When talking to Laverne Cox on the "E!" Red Carpet, Rodrigo said, "I wanted to do something fun and young but also we're at the Grammys, you know, it's glamorous, it's classy."

After opening the show with a performance of "Traitor," Rodrigo won three Grammy awards: best new artist, best pop solo performance for "Drivers License," and best pop vocal album for "Sour."

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