Celeb Style
Olivia Rodrigo's Fashion Evolution Will Have You Singing “Jealousy Jealousy”

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Despite only skyrocketing to mainstream music fame in 2021, Olivia Rodrigo has already undergone such a style evolution. From her days on High School Musical: The Musical: The Series (and even before that) to now serving as a fashion staple on red carpets, Rodrigo is a powerhouse of vocals and fashion, especially when it comes to her amazing Y2K aesthetic and unending ability to rock everything she touches.

Ever since the initial release of “Driver’s License,” Rodrigo’s life has been on a fast track. Now she’s a three-time Grammy winner with two record-breaking albums.

“Driver’s License” may have been her nationwide debut, but Rodrigo has been in the public eye much longer than you might have realized. In fact, her red carpet looks go all the way back to 2015. And when it comes to her fashion, her penchant for patterns, bright colors, and unflinching ability to remain unique and creative have only become more potent over the years.

Below, you’ll find Rodrigo’s ever-changing, yet always on point, style evolution. If you thought you knew all of her best ‘fits over the years, prepare to be surprised — there are for sure some amazing looks you’ve definitely have not seen before.

Olivia Rodrigo In April 2024: There’s No Doubt About Her Style

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Coachella 2024 was all about faves, old and new. Kesha joined Reneé Rapp on stage, Will Smith performed “Men in Black” during J. Balvin's set, and No Doubt — yes, the beloved pop punk band from the ‘90s and ‘00s — brought out Gen Z icon Olivia Rodrigo.

In the midst of OR’s headlining tour, she sung alongside Gwen Stefani, wearing a red bra and white tank top that read “I [heart] ND” as a shoutout to the group. She paired the look with winged black eyeliner, a bright red lip, and the blonde’s more signature hair buns.

Olivia Rodrigo In February 2024: Bringing Back Old Hollywood Glam

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Ahead of music’s biggest night — where she was nominated for six awards, including Record of the Year and Album of the Year — Rodrigo hit the red carpet looking like the epitome of Old Hollywood glam.

The singer wore a hip-hugging white Versace gown dripping in sapphires from top to bottom. The floor-length dress was originally worn in 1995 by supermodel Linda Evangelista, making this a serious throwback moment. (Rodrigo was born in 2003.)

Olivia Rodrigo In May 2023: Met Gala Round 3

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For her third Met Gala appearance, Rodrigo channeled her inner Audrey Hepburn in a custom black and white gown adorned with roses by Thom Browne.

Olivia Rodrigo In May 2022: Hello Met Gala Part Two

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Keeping things very Y2K at the 2022 Met Gala, Rodrigo decorated her hair with butterflies clips, and, no, they’re not the plastic ones from your childhood. She also went with a flowing, lilac gown designed by Versace that had it all. The dress featured sparkles, a slit, and a backless design with chains decorating it. Naturally, she had purple, platform heels to finish it off.

Olivia Rodrigo In April 2022: Modern Hollywood Glamour

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Olivia Rodrigo turned the glamour up to a 10 on the Grammys red carpet. Nominated for seven awards, Rodrigo donned over-the-elbow gloves and a gorgeous Vivienne Westwood gown that highlighted her figure with neon pink sparkle detailing. It’s giving old-school glamour with a little bit of cheeky sourness.

Olivia Rodrigo In February 2022: Cut Outs & Lace

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Who knew Rodrigo had a punk, goth side? Her party dress with the cut outs and garter effect is so intricate it almost looks like a spider had to have woven that webby design.

Olivia Rodrigo In January 2022: Crop Tops & Camo

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There’s so much to love about Rodrigo’s outfit from Jan. 2022. Her platform boots are so cool, and her pattern mixing with the camo skirt and patchwork shirt is both funky and perfectly executed.

Olivia Rodrigo In December 2021: Pumped-Up Platforms


The bow on Rodrigo’s black dress from 2021 is everything. With such an eye-catching pop, she hardly needed any other accessories, but that didn’t stop her from styling this look with a pair of trendy platforms. Ugh, she’s a woman after my own heart.

Olivia Rodrigo In November 2021: AMA Glam

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This sheer, Very Peri dress from the 2021 American Music Awards was such a moment for Rodrigo. The sequins caught the light perfectly, and the feathers around the skirt are add a fun, unexpected twist.

Olivia Rodrigo In October 2021: Y2K Fashion

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From the satin skirt to the corset to the beaded necklace, Rodrigo nailed the Y2K aesthetic with her streetwear look in October 2021. Is she going to give a master class or something? Because if so, you already know I’m taking notes.

Olivia Rodrigo In September 2021: Full-On Feathers

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In a Yves Saint Laurent lacy catsuit, Rodrigo blessed the Met Gala with her feathered-up ‘fit. As if that weren’t enough already, her dripping, sparkling earrings packed such a statement.

Olivia Rodrigo In July 2021: Commander In Clueless

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Who could ever forget Rodrigo’s Chanel tweed suit that she wore to the White House in 2021? It’s giving Cher from Clueless if she was tapped to speak about vaccines.

Olivia Rodrigo In May 2021: Eye-Popping Patterns

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This slip dress may be the best thing Rodrigo has ever worn. The print is loaded with hearts, cats, kiwis, and so many other items that’s a feast for the eyes to look at.

Olivia Rodrigo In 2019: High End High School

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Her look for the premiere of HSMTMTS in 2019 was a perfect mix of casual and dolled up. The tulle skirt and white t-shirt are fancy, yet you know she was comfortable at the end of the day.

Olivia Rodrigo In 2017: Bright Red Ruffles

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I’m obsessed with Rodrigo’s striped jumpsuit from 2017. The bright red ruffled collar and bold color make this a perfect look for summer. It’s not completely clear from here, but I think it even has pockets.

Olivia Rodrigo In 2016: Funky Florals

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In 2016, Rodrigo took to the red carpet in a vibrant, embroidered dress. The flowers are popping and vibrant. And to think, even all those years ago, she knew how to rock a red lip moment.

Olivia Rodrigo In 2015: Middle School Prep

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What a baby! In 2015, at just 12 years old, Rodrigo rocked a classic preppy-inspired outfit. Her jeans, denim top, and mustard sweater pair so well together. I was I was this well dressed in middle school.

No matter what year it is, you know Rodrigo’s bringing the drip.

Additional reporting by Elite Daily editors.

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