Olivia Rodrigo's Best Outfits of All Time

Since releasing her debut single "Drivers License" in January 2021, Olivia Rodrigo has become one of the biggest names in music. At the same time, she has also made an impact in the style world with her Y2K-inspired looks, glamorous red carpet outfits, and sustainable fashion. Take a look back at her best outfits

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Olivia Rodrigo's Black Outfit at the HSMTMTS Season 3 Premiere

OLIVIA RODRIGO, “HIGH SCHOOL MUSICAL: THE MUSICAL: THE SERIES” SEASON 3 RED CARPET PREMIERE EVENT - The cast of “High School Musical: The Musical: The Series” attends the Season 3 red carpet premiere at The Walt Disney Studios in Burbank, Calif. on Wednesday, July 27. The new season is now streaming exclusively on Disney+.

At the HSMTMTS season 3 premiere, where Rodrigo reunited with costar and rumored ex Joshua Bassett, the actress sported a Nensi Dojaka bodysuit with a matching mini skirt. She accessorized with some chunky jewelry by Dior and Bebe platform heels.

02 of 23

Olivia Rodrigo's Versace Gown at the 2022 Met Gala


At the 2022 Met Gala, the singer dazzled in a sparkling purple Versace gown, complemented with matching Jennifer Behr x Betsey Johnson butterflies in her hair and De Beers Jewellers diamonds, as a tribute to the silent film stars of the Gilded Age.

03 of 23

Olivia Rodrigo's Feather Dress

Olivia Rodrigo/Instagram
Olivia Rodrigo/Instagram

During an appearance on The Late Late Show With James Corden, Rodrigo sported a feathery AREA dress in bright neon colors.

04 of 23

Olivia Rodrigo's Dress at Billboard Women in Music in 2022

Olivia Rodrigo
Olivia Rodrigo. Amy Sussman/FilmMagic

In March 2022, Olivia Rodrigo wore an Area maxi dress with huge black boots as she attended the Billboard Women in Music event, where she was honored with woman of the year and gave a special performance of "Deja Vu."

05 of 23

Olivia Rodrigo's Alexandre Vauthier Gown at the 2022 BRIT Awards

The BRIT Awards 2022 – Red Carpet Arrivals
Gareth Cattermole/Getty

Rodrigo wowed at the 2022 BRIT Awards as she wore a silver gown by Alexandre Vauthier paired with black Giuseppe Zanotti wedge sandals.

06 of 23

Olivia Rodrigo's Saint Laurent Gown at the Opening Gala for the Academy Museum of Motion Pictures

Olivia Rodrigo attends The Academy Museum of Motion Pictures Opening Gala at The Academy Museum of Motion Pictures on September 25, 2021 in Los Angeles, California.
Amy Sussman/Getty

Rodrigo turned heads as she attended the Opening Gala for the Academy Museum of Motion Pictures in this strapless Saint Laurent column dress (which was also seen on Emily in Paris season 2). From the plunging neckline to the high slit, it was certainly one of her most daring looks yet.

07 of 23

Olivia Rodrigo's Lace Saint Laurent Catsuit at the 2021 Met Gala

The 2021 Met Gala Celebrating In America: A Lexicon Of Fashion

In yet another bold look, Rodrigo wore this sheer black lace off-the-shoulder Saint Laurent catsuit as she attended her very first Met Gala in 2021.

"I think Saint Laurent does a great job of making punk rock feminine, so that is what I was going for," Rodrigo told Vogue on the red carpet.

08 of 23

Olivia Rodrigo's David Koma Dress at the 2021 American Music Awards

Olivia Rodrigo attends the 2021 American Music Awards at Microsoft Theater on November 21, 2021 in Los Angeles, California.
Olivia Rodrigo. Matt Winkelmeyer/Getty

The High School Musical: The Musical: The Series star looked like a Disney princess (Ariel to be exact) as she sported this sequinned purple dress by David Koma at the 2021 American Music Awards, which she attended with singer and close friend Conan Gray.

09 of 23

Olivia Rodrigo's Versace Gown at the 2021 MTV VMAs

Olivia Rodrigo
Taylor Hill/FilmMagic

As Rodrigo walked the red carpet at the 2021 MTV VMAs, she looked stunning in a Versace gown with pink detailing. She accented the bright colors in the dress with pink lipstick and butterfly earrings, a nod to the imagery featured in her Sour album.

10 of 23

Olivia Rodrigo's Heaven by Marc Jacobs Dress at the 2021 MTV VMAs

Olivia Rodrigo performs onstage during the 2021 MTV Video Music Awards at Barclays Center on September 12, 2021 in the Brooklyn borough of New York City
Kevin Mazur/MTV VMAs 2021/Getty

As Rodrigo performed "Good 4 U" at the 2021 MTV VMAs, she sported a custom Heaven by Marc Jacobs lilac dress paired with matching gloves and butterfly clips in her hair. Going full riot grrl for the performance look, she pulled the entire ensemble together with fishnet tights and black Doc Martens.

11 of 23

Olivia Rodrigo's Pink Mini Dress at an MTV VMAs Afterparty

olivia rodrigo

The star's VMA afterparty look was equally eye-catching. She attended a party with friend Iris Apatow in a floaty pink mini dress paired with pink heels. In a separate image, she paired the look with some extravagant purple platform boots.

12 of 23

Olivia Rodrigo's Black Beret and Corset Top

olivia rodrigo

In an Instagram post, Rodrigo seemed to channel her American Girl character, Grace Thomas, as she wore a black beret. She pulled the whole look together with some graphic pants and a bustier corset.

13 of 23

Olivia Rodrigo's Calvin Luo Slip Dress at Variety's Hitmakers Brunch

Olivia Rodrigo
Rodin Eckenroth/FilmMagic

When Rodrigo was honored with the the Songwriter of the Year award at Variety's Hitmakers Brunch in December 2021, she kept things relatively simple with a black slip dress featuring a big green bow by Calvin Luo, strappy heels, and black stockings.

14 of 23

Olivia Rodrigo's Vintage Chanel Skirt Suit at the White House

Pop Star Olivia Rodrigo Arrives At The White House To Record Videos Promoting Covid Vaccinations
Chip Somodevilla/Getty

Rodrigo looked like Elle Woods herself as she wore a vintage plaid pink tweed skirt suit from Chanel during her 2021 visit to the White House. Of course, she made it perfectly Gen Z with towering Giuseppe Zanotti platforms.

15 of 23

Olivia Rodrigo's Custom Dior Haute Couture Outfit at the 2021 BRIT Awards

olivia rodrigo

For Rodrigo's debut performance of "Drivers License" at the BRIT Awards in 2021 (where she met music idol Taylor Swift backstage), the singer wore a custom Dior Haute Couture ensemble.

16 of 23

Olivia Rodrigo's Saint Laurent Dress at Saint Laurent Rive Droite Art Basel

Olivia Rodrigo
Alexander Tamargo/Getty

When Rodrigo attended the Saint Laurent Rive Droite Art Basel in Miami Beach in November 2021, she played up her little black dress with some playful braids and silver jewelry.

17 of 23

Olivia Rodrigo's Ashley Williams Dress

olivia rodrigo

Rodrigo looked pretty in pink as she sported this off-the-shoulder dress from Ashley Williams. She pulled the whole look together with a heart necklace by Stinky Jewelz.

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Olivia Rodrigo's DSQUARED2 Dress

olivia rodrigo

Rodrigo looked like the sixth member of the Spice Girls as she wore this mini plaid dress by DSQUARED2 paired with buckled platform boots and pigtails.

19 of 23

Olivia Rodrigo's Vintage Betsy Johnson at Sour Prom

olivia rodrigo

For the celebration of her Sour Prom concert, Rodrigo wore a vintage Betsey Johnson pink lace slip dress paired with glittery blue sandals, pearl necklaces, and bubble braids.

20 of 23

Olivia Rodrigo's Réalisation Par Dress

Olivia Rodrigo/Instagram
Olivia Rodrigo/Instagram

Further proving that she's a style icon in training, this Réalisation Par dress, the item quickly began selling out online after Rodrigo shared a photo of her wearing it online. Giving us major early 2000s vibes, she even paired the outfit with a vintage Twilight bag and some edgy jewelry.

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Olivia Rodrigo's Vivienne Westwood Set on Saturday Night Live

Olivia Rodrigo
Will Heath/NBC/NBCU Photo Bank via Getty

It was only fitting that for the debut performance of her punk rock hit "Good 4 U" on Saturday Night Live, Rodrigo wore an equally edgy outfit. She seemed to channel pop icons Avril Lavigne and Gwen Stefani as she sported a plaid corset top and trousers by Vivienne Westwood.

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Olivia Rodrigo's Floral Yellow Set at a HSMTMTS Press Conference

olivia rodrigo
Mark Von Holden/Invision/AP/Shutterstock

Proving that she has always had a major eye for fashion, Rodrigo wore this cute yellow floral oversized suit as she attended a press conference for High School Musical the Musical the Series season 1 in 2019.

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Olivia Rodrigo's Cardigan on People Now

Olivia Rodrigo
Jason Mendez/Getty

When Rodrigo and the rest of the HSMTMTS cast stopped by People Now in 2019, the singer seemed to channel her inner Wildcat as she wore this cute red and black cardigan with flared jeans and red heels.

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