Olivia Rodrigo’s best fashion looks, from Vivienne Westwood at the Grammys and Chanel to meet Joe Biden, to posing with Taylor Swift in Dior and giving retro 2000s style a Gen Z update

Apr 6 , 2022

Olivia Rodrigo, winner of the awards for best pop vocal album for “Sour,” best new artist and best pop solo performance for drivers license, poses in the press room at the 64th Annual Grammy Awards at the MGM Grand Garden Arena on April 3, in Las Vegas. Photo: AP Photo

Rodrigo takes an unconventional approach to fashion, donning noughties looks that take us back to the heydays of Paris Hilton and Britney Spears

The teenage pop sensation and Disney alum wore an iconic vintage Chanel suit when she met President Joe Biden at the White House to promote Covid-19 vaccinations

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.

1. She made her Grammys debut in Vivienne Westwood

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

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.