All of Olivia Rodrigo's most daring looks

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.

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."

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.

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.

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."

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.

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 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."

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.

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."

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."

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.

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."

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.

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."