30 Olivia Rodrigo Style Moments That Embody Her Ultra-Cool Gen-Z Energy

While she’s first and foremost one of Gen-Z’s biggest pop stars with two smash-hit albums and several Grammys under her belt, Olivia Rodrigo is also an undeniable rising fashion icon. Her countless best-dressed moments, numerous Met Gala appearances, and edgy street style have helped the musician stand out in a sea of fashion-oriented celebrities. Major credit is due to her stylists as well as to fashion choices that stay true to her personality, be it nods to the grunge aesthetic, Old Hollywood glamour, or archival moments that offer a new spin on ’90s and Y2K favorites. The “Vampire” singer loves an edgy, sheer statement on the red carpet, plus her love for vintage clothing catches the eyes of fashion lovers far and wide. Not to mention, she’s always on the hunt for up-and-coming designers, and it’s guaranteed that Gen-Z will flock to whoever and whatever she wears. Ahead, check out 30 of Olivia Rodrigo’s best style moments, from the red carpet to the streets of New York City and beyond.

Grammy Awards (2023)

For the 2023 Grammys, Rodrigo went for a pared-back "naked dress" moment, wearing a black sheer Miu Miu gown with high-waisted underwear. She accessorized with only a simple pendant-style necklace, allowing the look's understated details to shine.

Governors Awards (2024)

Rodrigo channeled classic glamour for the 2024 Governors Awards, opting for a vintage strapless Yves Saint Laurent black gown and a red lip. Is there a better combination? We think not.

'The Hunger Games: The Ballad Of Songbirds And Snakes' Fan Event (2023)

Rodrigo wrote and performed the ballad "Can't Catch Me Now" for The Hunger Games: The Ballad Of Songbirds And Snakes, adding to her long list of achievements. She attended a red carpet event for the film wearing a black sequined halter gown by Rodarte, which featured pink and purple floral detailing around the neckline.

'Guts' Album Release Party (2023)

What better way to celebrate a sophomore album than with an iconic ensemble? To fête the release of Guts, Rodrigo wore this archival set from Todd Oldham's spring 1995 collection, which combines pieces that Shalom Harlow and Amber Valletta originally wore in a runway moment that made fashion history. We have stylist Jared Ellner to thank for this incredible revival.

MTV Video Music Awards (2023)

To say Rodrigo sparkled at the 2023 VMAs would be an understatement. The “Get Him Back!” singer channeled disco ball energy in a floor-length silver gown by Ludovic de Saint Sernin, made with Swarovski crystal mesh.

Grammy Awards (2022)

For being a first-time nominee, Rodrigo had quite the 2022 Grammys. The "Drivers License" singer took home three big awards (Best Pop Vocal Album, Best New Artist, and Best Pop Solo Performance), plus a well-earned spot on our hypothetical best-dressed list. For the occasion, she slipped into a corseted Vivienne Westwood gown with pink crystal illusion detailing and a pair of on-trend black opera gloves for the evening.

Met Gala After Party (2023)

Rodrigo hit the Met Gala after party in it-girl fashion, opting for a vintage Chanel sequined dress from 1994. She also ditched the micro bangs she sported while walking the Met Gala red carpet, returning to her tried-and-true, free-flowing locks.

Vanity Fair Oscar Party (2023)

For the 2023 Vanity Fair Oscars afterparty, Rodrigo stunned in a floor-length, sequined leopard print gown from Valentino’s Pre-Fall 2023 collection. The musician let the dress take center stage, only accessorizing with a simple pair of sparkly earrings.

Billboard Women In Music (2023)

Of course, a modern style icon like Rodrigo would dare to rock a bold pair of horse print trousers that Stella McCartney created while at Chloé in 2001. The laid-back look was complete with a brown leather strapless tube top, and all in all, this is a horse girl aesthetic we can get behind.

Universal Music Group's Grammys Afterparty (2023)

Fashion girlies can spot this 16Arlington sequined mini dress from a mile away. Rodrigo paired the beloved cutout LBD with a pair of black platform heels.

American Music Awards (2021)

One thing about Olivia Rodrigo is that she loves a sheer moment, especially on the red carpet. She went bold for the 2021 American Music Awards, wearing a David Koma sparkly sheer dress with a feather-trimmed bottom.

Met Gala (2022)

Rodrigo may be relatively new to the Met Gala steps, but her looks have already found a place in best-dressed history, especially this one from 2022. The singer channeled Y2K vibes in the best way possible with a glittering Versace gown, sheer purple gloves, and butterfly hairpins.

Met Gala (2023)

For her most recent Met Gala look, Rodrigo channeled Old Hollywood glamour to a T. Her Audrey Hepburn-inspired updo and black-and-white floral number from Thom Browne fit right in with the evening’s theme: “Karl Lagerfeld: A Line of Beauty.”

GQ Men of the Year Party (2023)

Here, Rodrigo embraced her inner flapper girl with a fringed Tom Ford LBD that would have us twirling all night long. She went low-key on the accessories front and paired the flirtatious dress with black platform heels.

MTV Movie & TV Awards (2022)

Rodrigo ruled the red carpet yet again at the 2022 MTV Movie & TV Awards, when she arrived in this vintage black corseted Jean Paul Gaultier dress. The dress oozed cool in itself, but Rodrigo brought the look to the next level with a spiky hairdo and black strappy heels.

White House Visit (2021)

While visiting the White House to encourage young people to get vaccinated, Rodrigo traded her edgy aesthetic for a more presidential vibe. The singer opted for an on-trend tweed skirt suit from the Chanel archives (so chic), but of course, she put her own spin on the preppy look with Giuseppe Zanotti white platform heels and a micro Amina Muaddi black purse.

Met Gala (2021)

Rodrigo's 2021 Met Gala debut belongs in the punk princess hall of fame. The musician honored the evening's theme, "In America: A Lexicon of Fashion," in an off-the-shoulder Saint Laurent catsuit that featured sheer lace fabric and a feathered neckline. She accessorized the punk moment with a pair of platform heels and lots of jewels.

Interscope Records and LACMA Art Presentation (2022)

Rodrigo honed in on Gen-Z style while attending an art presentation for Interscope Records and LACMA. The singer's sweater, camo skirt, and sky-high boots were all courtesy of the Heaven by Marc Jacobs spring 2022 collection.

Grammy Awards Performance (2022)

If you're performing at the Grammys, you have to bring your fashion A-game—and naturally, Rodrigo did during her 2022 Grammy Awards performance. The star embodied pop-punk with a flowy dress, fishnet tights, and a pair of black platform combat boots.

MTV Video Music Awards (2021)

Rodrigo's 2021 MTV Video Music Awards look was straight from the archives, as many of her best looks are. She chose a corseted orange-and-fuchsia vintage Versace gown from the Spring 2001 Atelier Collection, pairing it with pink dangle earrings and platform heels.

Academy Museum Opening Gala (2021)

Rodrigo attended the star-studded Academy Museum of Motion Pictures Opening Gala in this daring YSL number. The strapless black gown featured a plunging neckline and a high slit.

Brit Awards (2021)

For the 2021 Brit Awards, Rodrigo opted for another sheer moment—but this time in ruby red. While performing her song “Drivers License” on stage, the singer wore a custom Dior couture dress with sequined undergarments and a sheer overlay.

Billboard Women in Music (2022)

Rodrigo channeled her inner punk rocker again for the 2022 Billboard Women in Music event. She wore a white crystal-embellished maxi dress by Area, featuring three black belts wrapped around the dress's bodice.

Brit Awards (2022)

While attending the Brit Awards for the second time, Rodrigo shimmered in a sequined Alexandre Vauthier dress. She went minimal on the accessories, allowing the dress to shine on its own.

'Olivia Rodrigo: Driving Home 2 U (A Sour Film)' Premiere (2022)

Rodrigo embraced all things coquette with her look for the premiere of her film with Disney+. The black-and-pink bow look was courtesy of the brand Fancì Club, a Gen-Z-loved brand Rodrigo has been spotted in before.

Out in NYC (2022)

Rodrigo is the queen of Gen-Z street style, and that's just a fact. While out and about in NYC, the singer wore a silky black lingerie-style mini dress, expertly styled with a pair of black loafers and white ankle socks.

Sour Prom Concert (2021)

While Rodrigo was too busy becoming famous to attend her own prom, she threw one in honor of her first album, Sour, and of course her look was cooler than any other high schooler's. She wore a pink vintage Betsey Johnson dress paired with bright blue platform heels and bubble braids.

Variety's Hitmakers Brunch (2021)

While attending Variety’s Hitmakers Brunch, Rodrigo went for another bow moment in a Calvin Luo minidress with sheer black knee-high socks and a pair of platform Mary Janes.

Art Basel Event (2021)

Rodrigo channeled her inner Wednesday Addams while at the Saint Laurent Rive Droite event at Art Basel in 2021. She paired her sparkly LBD with sheer black tights, black pointed-toe heels, and a few statement necklaces, then finished the look with her long locks tied into two pigtail braids.

People Now Appearance (2019)

Before Rodrigo became the mega-star we know her as now, she still had a knack for style. While on a press trip in NYC, the HSMTMTS star wore a red, black, and white striped cardigan with flared jeans and pointed-toe heels featuring red accents.