Olivia Rodrigo’s Hottest Fashion Moments—From Performing on Stage to Walking the Red Carpet

There’s no denying the singer has guts, often taking just as many risks with her fashion as she does with her music.

Allie Hayes | 21 Hours Ago

Olivia Rodrigo / Kevin Mazur/Getty Images/Live Nation

It’s safe to say Olivia Rodrigo has guts—and that goes for both the title of her latest album and her awe-inspiring wardrobe.

The 22-year-old actress and singer got her start starring on Disney+’s humorously titled hit show High School Musical: The Musical: The Series before positively taking over the music industry (and the entire world) with her debut single “drivers license” back in 2021. Her star was catapulted further with the release of her debut album, Sour, which she followed up with an equally beloved sophomore effort, Guts—the latter of which also received the concert film treatment courtesy of Netflix.

While her career has been incredible so far, so have her fashion choices, often serving as one of the most stylish celebrities on any red carpet or at any event she attends. So, with that in mind, let’s take a look back at just 10 of the superstar’s hottest moments over the years:

Lollapalooza, 2025

Kicking things off with a recent viral moment, we have Rodrigo’s custom red leather bodysuit by Ludovic de Saint Sernin, which she wore while headlining Lollapalooza for the first time. This outfit broke the internet the second she took the stage, shocking fans with the risky rock n’ roll-inspired look, which consisted of a cherry-red, high-cut leather bodysuit that appeared all-but-molded to her form, with strategically placed straps hugging her hips and the dipping neckline. She paired the bodysuit with black knee-high, lace-up combat boots, committing fully to the grunge aesthetic.

The Grammy Awards Red Carpet, 2025

Next up on our list is this breathtaking vintage cutout gown by Versace, which Rodrigo wore to the 2025 Grammy Awards. The top of the piece began in a choker-style around the neck, careening down the body before criss-crossing, overlapping and connecting to the mermaid-style skirt, leaving the back of the gown open for a truly sultry look. This Old Hollywood-inspired glam was finished off with a classic cat-eye makeup look, teardrop earrings and a matching bracelet.

The Premiere of Her Concert Film for Guts, 2024

There’s no way we can move any further down this list without chatting about this vintage Christian Dior by John Galliano number, which Rodrigo donned for the premiere of her Guts concert film. Appropriately worn in her signature purple shade, this sleek and sensual lingerie-inspired dress featured an all-over print reminiscent of lace with a flattering band design around the waist, giving Rodrigo an effortlessly cool look for what was surely one of the most exciting nights of her career.

The Rock N’ Roll Hall of Fame Induction Ceremony, 2022

Let’s dig a little farther back into Rodrigo’s fashion history for this next entry on our list, which is, of course, this must-see dark gray mini-dress with side and back cutouts by Shushu Tong. Rodrigo donned this stylish ensemble while inducting icon Carly Simon into the Rock N’ Roll Hall of Fame back in 2022, where she also sang a rendition of Simon’s hit, “You’re So Vain.” She paired the sweet mini-dress with black thigh-high stockings to add a touch of sex appeal, completing the look with a chunky heel and choker necklace.

Her 21st Birthday Party, 2024

Playfully captioning this photo set, “today is my last day of being able to underage drink (hypothetically) !!!!” the next entry on our list saw Rodrigo go all out for her 21st birthday back in 2024, sporting the ultimate little black dress and stiletto heel combo. This mini-dress featured a plunging neckline and cutouts all over, giving off the aura of a punk rock Greek goddess, with Rodrigo’s updo, hoop earrings and red lip the perfect accessories to finalize the ‘fit.

The American Music Awards Red Carpet, 2021

And who could forget this delightfully funky gown by David Koma, which Rodrigo wore for the 2021 American Music Awards? The semi-sheer periwinkle dress hugged Rodrigo’s figure in a stunningly snug fit, her darker, high-waisted undergarments visible beneath the heavily sequinned fabric. With the dipping neckline left bare to allow the dress to fully shine (literally—it was so sparkly!). With a halter-style neckline and mermaid silhouette, the real star of the gown was, of course, the thick band of blue feathers running around the hemline.

Her Appearance on The Tonight Show Starring Jimmy Fallon, 2024

And here we have another Ludovic de Saint Sernin number to add to the list, as Rodrigo sported this strappy red mini-dress from the brand while being interviewed by Jimmy Fallon on The Tonight Show to promote her aforementioned Guts concert film. The glossy get-up was constructed in a way that almost made it look like stacked studded belts, which was enough to make any retired emo kid swoon, and it proved to be the perfect choice for chatting with Fallon about that time she was almost arrested after being confused with a criminal (no, really, check out the interview).

The Academy Museum of Motion Pictures Opening Gala, 2021

There was likely some kind of earthquake back in 2021 as a direct result of so many jaws dropping to the floor when Rodrigo stepped out in this gown by Saint Laurent for the Academy Museum of Motion Pictures Opening Gala. The breathtaking strapless black number was equal parts sexy and sensual, featuring a truly unique cutout in the front to create a daringly deep neckline, which the singer chose to keep bare to fully embrace the risqué look.

Her First Met Gala, 2021

And speaking of Saint Laurent, Rodrigo started her first-ever Met Gala appearance in 2021 on a high note, donning this sheer lace catsuit by the designer brand rather than going for the typical themed gown. Accented with a gorgeous off-the-shoulder feather neckline with high-waisted black panties peeking through the lace, this outfit cemented Rodrigo as one to watch out for at future Met Galas. Hey, speaking of...

And Finally: The Met Gala (Again!), 2022

Ending our list on the highest note possible with my personal favorite Olivia Rodrigo look of all time (yes, me—hi, hello, I’m the real-life human writing this article): her 2022 Met Gala ensemble. From head to toe, this look is the definition of “ethereal.” The sparkling purple gown by Versace was positively to die for, and the matching sheer gloves and butterflies in her hair—which were revealed to be a last-minute addition during her Vogue “Get Ready with Me” video—were inspired decisions by her stylists, further putting this already gasp-worthy glam over the top. She quite literally looks like a real-life fairy princess. It’s been three years, and I’ve yet to recover from this one (just in case that’s not abundantly apparent).

Published 21 Hours Ago

ALLIE HAYES

Allie Hayes is an experienced pop culture staff writer and editor specializing in movies, TV and celebrity news. Before joining the Sports Illustrated Swimsuit team as a Breaking/Trending News Editor, she worked at several outlets including BuzzFeed, The Daily Dot, and Newsweek. When she’s not writing for work (or writing for fun), you’ll find her curled up on the couch reading yet another romance novel, obsessively watching pro wrestling with her friends, or taking blurry photos of her two adorable cats.