The 64th annual Grammy Awards took place on April 4 this year at Las Vegas’ MGM Grand Garden Area. Though the Oscars’ Will Smith chaos from the week before continues to loom, the Grammys appeared free from drama and focused on celebrations of the best of new and old talent. Among the newbies, teenage pop sensation Olivia Rodrigo stole the spotlight, taking home three awards including best new artist and best pop vocal album. One unfortunately broke when she was backstage with reporters, but we’re sure there will be plenty more to come. The breakout star has risen to meteoric fame over the past couple of years thanks to the success of her song drivers license , a throwback to adolescent heartbreak, and acting gigs with Disney. At only 19, Rodrigo’s influence reaches over 23 million followers on Instagram, 13 million on TikTok and eight million on YouTube – and with celebrity status comes a fashionable wardrobe. The superstar’s adoption of 90s and 2000s inspired looks has sparked attention from designers worldwide as she revives Y2K trends – think cropped tees, plaid miniskirts and platform boots. Here, we take a look at Rodrigo’s best fashion moments to date. The luxury lives of Kourtney Kardashian’s children 1. She made her Grammys debut in Vivienne Westwood View this post on Instagram A post shared by Olivia Rodrigo (@oliviarodrigo) Rodrigo opted for a Vivienne Westwood off-shoulder black dress with pink and black crystal detail to accentuate her figure, accessorised with black opera-length gloves and layered chokers. Glamour called the ensemble a look fit for Bridgerton – and we could definitely see Rodrigo playing a pretty damsel in distress in the series. 2. The Gen Z pop star accepted her Billboard award in an Area dress View this post on Instagram A post shared by Olivia Rodrigo (@oliviarodrigo) On March 2, when accepting the Billboard Woman of the Year award, the High School Musical: The Musical: The Series sensation rocked a flowing white maxi dress from New York-based label Area, strapped at the waist with a three-belt crystal-embellished harness and black buckled straps to lend something of a dominatrix twist. Rodrigo paired the dress with grungy combat boots – all contrasting, or perhaps complementing, her oh-so-sweet persona. How rich is Lady Gaga really? Inside her gigantic net worth 3. She was a sparkling mermaid at the American Music Awards Dazzling in a sequinned lilac halter gown with a feathered hem, Rodrigo stunned in a mermaid-like ensemble for her first appearance at the AMAs in November 2021. The gown, designed by David Koma, was paired with silver heeled sandals. She returned home with multiple awards from the ceremony, including best new artist. 4. Her show-stopping plunge Saint Laurent dress View this post on Instagram A post shared by Olivia Rodrigo (@oliviarodrigo) Then 18, Rodrigo turned heads at the Academy Museum of Pictures Opening Gala in September 2021 in her sultry black slit-detailed dress. The Saint Laurent custom piece was from the luxury French house’s spring 2020 collection. 9 Oscar-nominated child stars and where they are now 5. A vintage Chanel suit when she met President Joe Biden View this post on Instagram A post shared by Olivia Rodrigo (@oliviarodrigo) As the unofficial spokesperson for millennials and Gen Zs in the United States, Rodrigo was invited to the White House to use her voice to encourage Covid-19 vaccinations among the youth in July 2021. Arriving in a feminine-chic pink tweed Chanel blazer-skirt combo from 1995, the artist looked marvellous in what has been dubbed a graceful Jackie Kennedy-meets-Cher Horowitz (Clueless) interpretation. 6. Off the red carpet, Rodrigo goes for noughties looks olivia rodrigo at a grocery store is my favorite aesthetic pic.twitter.com/IOZ04u3YdP — dani ⋆*. (@livsholIand) August 5, 2021 Baby tees with a miniskirt and combat boots are a regular go-to look for Rodrigo, reviving an aesthetic mastered by the queens of the noughties, Paris Hilton and Britney Spears. For a trip to the supermarket in July 2021, she stepped out in a Marilyn cropped T-shirt from Mimi Wade with a grey low-waist pleated miniskirt by No Dress. And let’s not forget the 90s sunglasses. Not just Jada Pinkett Smith – 10 celebrities who suffer from alopecia 7. She pulls off grunge, but makes it cute View this post on Instagram A post shared by Olivia Rodrigo (@oliviarodrigo) The style icon has a flair for punk – and a good eye for old-school looks with a generational update. In June 2021, she posted an Instagram shot of her in a Dsquared2 red plaid print dress with knee-high platform heels from Marc Jacobs for a playful outfit that Sk8er Boi ’s Avril Lavigne would probably approve of. 8. Rodrigo met her idol Taylor Swift in a custom Dior View this post on Instagram A post shared by Olivia Rodrigo (@oliviarodrigo) Think … disco diva meets boho. The American singer, who has Filipino, German and Irish ancestry, took to the stage to perform her hit single drivers license at the BRIT Awards in May 2021 in a gorgeous custom red gown by Dior created in part by British stylist Anna Hughes-Chamberlain. The head-to-toe crimson-coloured goddess stunned in the sheer piece, which revealed a matching sequin bra and shorts underneath. A bold look indeed, but classy nonetheless. It was also the day she got to meet her idol, Taylor Swift. Want more stories like this? Follow STYLE on Facebook , Instagram , YouTube and Twitter .