Olivia Rodrigo’s Style Evolution: From Disney Cutie to Pop Sensation

Before Olivia Rodrigo was a Grammy-winning superstar who broke our collective hearts with her relatable songwriting and vulnerability, she was a child actress who rose to fame with her role as Nini in the popular Disney+ show High School Musical: The Musical: The Series. 

Her breakthrough debut album, 2021’s Sour, spent five weeks atop the weekly Billboard 200 in June-July 2021 and launched a pair of Hot 100 No. 1s in “Drivers License” and “Good 4 U.” The set finished at No. 2 on the year-end Billboard 200 Albums tally in 2021, while “Good” and “License” are Nos. 5 and 8, respectively, on the same year-end Hot 100 Songs recap.

Rodrigo was also No. 1 on Billboard’s 2021 year-end Hot 100 Artists, Hot 100 Songwriters, Billboard Global 200 Artists, Streaming Songs Artists, Pop Airplay Artists and Billboard Canadian Hot 100 Artists rankings. She was honored as Woman of the Year at the 2022 Billboard Women in Music ceremony.

And while she has always been talented, she has also always been stylish. Just like the rest of us, Rodrigo used to experiment with her style before landing on her envy-worthy punk rock-meets-Y2K looks that she brings to red carpets, interviews, onstage and beyond — trying out everything from patterned minidresses to sleek jumpsuits.

See below as we take a trip down memory lane to relive her complete style evolution stemming all the way back to 2016, when a then 13-year-old Rodrigo walked the red carpet for the premiere of Adventures in Babysitting.