By Neia Balao
10:59am PDT, Aug 27, 2022
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Olivia Rodrigo has evolved from Disney darling to three-time Grammy-winning pop star at just 19. As her music career grows and flourishes, fans have taken an interest in not just Olivia's hit songs but her fashion choices, which often combine girlie silhouettes with a glamorous grunge vibe — an homage to the styles of the late '90s and early '00s. Join Wonderwall.com as we take a look at Olivia's best — and weirdest — fashion moments, starting with this look… Olivia was spotted leaving a New York City recording studio in August 2022. The "brutal" singer wore a black baby tee, a red plaid miniskirt and Doc Marten boots. She finished off her grungy laidback look with two simple braids and a canvas tote bag.
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In March 2022, Olivia Rodrigo attended the premiere of her movie "Driving Home 2 U (A Sour Film)" in a pink-and-black ensemble — a corset adorned with bows, matching opera gloves and a miniskirt courtesy of Fancí. Chunky platform heels with a rounded toe from GCDS and knee-high stockings from Wolford completed the look. The ensemble perfectly embodies Olivia's sartorial DNA — femininity with just the right amount of edge.
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In March 2022, Olivia Rodrigo attended the Billboard Women in Music Awards where she accepted the Billboard Woman of the Year honor. For the occasion, the "deja vu" singer wore a gorgeous Area maxidress with crystal detailing on the bodice. She added extra oomph to the look with a chunky three-piece Area leather belt featuring crystal-embellished statement buckles and further accessorized with GCDS lace-up platform boots and rings from Pandora.
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Olivia Rodrigo attended the season 3 premiere of "High School Musical: The Musical: The Series" in July 2022 in a look that was true to her eclectic style — a strapless Nensi Dojaka minidress featuring a cutout and sheer panel below the bust. She paired the edgy LBD with black patent platforms and Y2K-themed jewelry including a Dior choker and dangling earrings.
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In May 2022 following the Met Gala, Olivia Rodrigo switched out of her slinky Versace gown and into another frock for an afterparty. She's seen here out and about in New York City in a pink-and-red houndstooth-patterned Versace minidress paired with Wolford tights and Versace Medusa platform pumps. While the look definitely encapsulated her nostalgic spirit, we could've done without the braided pigtails!
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At the MTV Movie & TV Awards in June 2022, Olivia Rodrigo showed her love for vintage when she stepped out in a 1990s Jean Paul Gaultier corset gown. She paired the ultra-feminine, figure-flattering frock with Alexander Wang sandals and earrings by Outhouse.
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At the 2022 BRIT Awards, Olivia Rodrigo put the perfect spin on a slip dress when she arrived in this jaw-dropping Alexandre Vauthier piece embellished with delicate square sequins. The pop prodigy paired her glamorously grunge dress with Stefere earrings, Djula and Poche rings and Giuseppe Zanotti wedges.
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In April 2022, Olivia Rodrigo attended her first Grammy Awards, where she took home three honors: best new artist, best pop album and best pop vocal performance. The singer-actress showed up in an off-the-shoulder Vivienne Westwood confection embellished with a glittery pink outline of her silhouette that seemed in line with Olivia's aesthetic but wasn't one of our favorite looks on the star.
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Olivia Rodrigo, seen here in April 2022 ahead of her performance at Radio City Music Hall in New York City, has certainly proven that her street style is just as worthy of attention as her red carpet fashion! The "SOUR" songstress donned a Heaven by Marc Jacobs vest, a Praying plaid miniskirt, TUKskin creepers and a classic Chanel flap bag.
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OK, so maybe she wasn't totally on theme… but does that really matter when she looked this good?! Second-time Met Gala attendee Olivia Rodrigo showed up to the May 2022 event — which featured the theme "In America: An Anthology of Fashion" — in a shimmery lavender metal-mesh Versace dress. She finished off the look with sheer purple gloves, sparkly heels and an array of De Beers jewelry.
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As for Olivia Rodrigo's first Met Gala in 2021? Well, her look wasn't quite as big of a hit. The "drivers license" singer took to the steps of the "In America: A Lexicon of Fashion"-themed event wearing a sheer black lace Saint Laurent jumpsuit with feathered trim at the neckline plus diamonds and platform peep-toe heels.
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Olivia Rodrigo showed up to the 2021 American Music Awards in a stunning sheer periwinkle frock that was absolutely to die for. The sequined design by David Koma also featured a plunging neckline and statement feather trim.
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There's something delightfully quirky about what Olivia Rodrigo donned for the Variety Music Hitmakers Brunch in December 2021 — a Calvin Luo slip dress with a statement olive green bow, which she wore over a Tankair mesh top. She accessorized with crystal-embellished Wolford x Amina Muaddi socks and Nodaleto platform Mary Janes.
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Olivia Rodrigo rocked head-to-toe Saint Laurent when she attended the luxury fashion house's Rive Droite Art Basel event in November 2021 — a silk Georgette dress, Viper pumps and an Emmanuelle bag.
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At the Academy Museum of Motion Pictures opening gala in September 2021, Olivia Rodrigo stepped outside of her comfort zone when she debuted a skin-baring Saint Laurent look. The "brutal" songstress donned a black floor-length design by Anthony Vaccarello with a thigh-high slit and cutouts along the bodice. While we commend her for donning her most risqué look yet, we wish we could've seen her in a different silhouette.
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Olivia Rodrigo showed off her love for aughts fashion in January 2022 as she left a Spotify party — with bestie Conan Gray — in a black silk bustier corset from Alexander McQueen's Fall 2002 collection, a pale green ballerina-themed skirt from Jean Paul Gaultier and leather platform buckle-embellished boots from Marc Jacobs.
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Olivia Rodrigo in vintage Atelier Versace?! We love to see it. At the 2021 MTV Video Music Awards, the three-time Moon Person trophy winner — who took home honors for best new artist, song of the year and PUSH performance of the year — wore a romantic peach satin gown with a boned bodice covered in draped fuschia tulle.
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At the 2022 iHeartRadio Music Awards, Olivia Rodrigo hit the red carpet in a purple Versace minidress paired with latex leggings. The frock featured Olivia's signature corset bodice and gave off an '80s rocker feel.
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Olivia Rodrigo headed to an appearance on "Jimmy Kimmel Live" in October 2021 in an adorable getup consisting of a plaid corset top, a bright green satin skirt and Dr. Martens platform boots.
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Olivia Rodrigo showed her love for chunky knits as she left New York City's American Girl store in April 2022. The "good 4 u" rocker — who starred in the 2015 movie "American Girl: Grace Stirs Up Success" — sported the Heaven by Marc Jacobs' brace face sweater, a blue plaid skirt and combat boots.
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Not all vintage pieces should come back! While we adore Olivia Rodrigo's love for all things '90s and early aughts, this Betsey Johnson frock she wore after performing at Radio City Music Hall in New York City in April 2022 looked peculiar at best.
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How darling is she?! At the 2021 BRIT Awards, Olivia Rodrigo donned a neon yellow tulle gown from Dior. She finished off the look with black platform sandals.
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In July 2021, Olivia Rodrigo looked all sorts of sophisticated when she arrived at the White House to promote COVID-19 vaccinations. For the high-profile appearance, she went for a polished and chic look in a vintage black, white and pink Chanel tweed suit, white Giuseppe Zanotti platform heels paired with black socks and an Amina Muaddi purse.
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Happy Birthday, Olivia! In February 2022, Olivia Rodrigo left her birthday party in Los Angeles wearing a black lace-trimmed pink camisole top and matching skirt from No Dress, black platform heels from Naked Wolfe and a glittery "Birthday Girl" cowboy party hat.
