Ask any Gen Z-er and they’ll tell you: Olivia Rodrigo is the people’s pop-punk princess.

An icon of Y2K-revival style, the 21-year-old actress and singer has had a meteoric rise to fame sparked by the internet craze that ensued after the release of her 2021 single “drivers license.” Two studio albums and three Grammy awards later, Rodrigo is a bona fide pop star. All along the way, we’ve admired her signature sense of style.

The hallmarks of a true Rodrigo ensemble include (but are not limited to) serious sequins, playful prints, and splashes of purple (the colour of both her SOUR and GUTS albums) with an overarching pop-punk influence.

On tour, she’s partial to rocker-chic fishnets, plaid, bedazzled bralettes and hot pants. Off stage and on to the red carpet, she frequently taps stylists Chloe and Chenelle Delgadillo as well as Danielle Goldberg to put together Y2K-inspired looks that always turn heads.

In celebration of the Canadian leg of her GUTS world tour kicking off this week in Montreal, we’re looking back at some of Rodrigo’s best looks ever.

Olivia Rodrigo’s Best Style Moments

 

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The pop star made her Met Gala debut at 2021’s In America: A Lexicon of Fashion-themed event wearing a lacy Saint Laurent jumpsuit complete with a chic feather trim.

For her first American Music Awards appearance, the “deja vu” singer stepped out in a semi-sheer sequin gown designed by David Koma with another fun feathered bottom.

 

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The feather obsession continued when Rodrigo wore a fitted pink, blue and purple houndstooth patterned mini dress on The Late Late Show couch in March 2022.

Bringing Y2K back like it never left, Rodrigo’s custom 2022 Grammy’s after-party dress by Blumarine was a total nod to Paris Hilton with its layered ruffles and plunging neckline.

 

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A vision of ethereal beauty, Rodrigo walked the 2022 Met carpet in a glitzy purple Versace gown paired with matching platform heels and sheer lilac opera gloves.

 

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Well ahead of the leopard print renaissance, the “obsessed” singer donned a floor-grazing halterneck number in fashion’s favourite animal print at the 2023 Vanity Fair Oscars Party.

 

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Never one to shy away from a bedazzled moment, Rodrigo arrived at the 2023 VMAs wearing a custom Ludovic de Saint Sernin gown made of 150,000 Swarovski crystals.

At the 2024 Grammys in February, Rodrigo went the Old Hollywood route with a cream-coloured archival Versace dress from the 1995 Spring Summer collection.

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