Olivia Rodrigo Tried Fall’s “Prep School Pin” Trend

Alongside the hold “Driver’s License” had on TikTok, the world at large first really met miss Olivia Rodrigo as public school icon Nini on High School Musical: The Musical: The Series. During her actual senior year of high school, she was busy recording an album. Remember Sour? Of course you do.

Still… the singer looks perfectly at home wearing a Prep School Pin in her hair. It’s a look that unites us all, regardless of education trajectory, rivalry (East High vs. West High, obviously), or if you were team Serena instead of Blair.

Olivia Rodrigo’s “Prep School Pin” Hair

Last Thursday, the singer concluded her Guts album era with a surprise show in New York. She took the stage with her famous brown locks elegantly curled and pinned back with a single bobby pin, a style we’re calling the “Prep School Pin” and are happy to educate you on.

Rodrigo’s look was the work of celebrity hairstylist Rena Calhoun. Armed with a cherry red La Bonne Brosse brush and her bobbies, she fixed the Grammy winner’s long hair into a side part and slid the simple hair accessory into place. These two things—the singular clip and side part—are the two biggest markers of the trend, which you can create with any hair texture (though those old Hollywood waves are something special).

The Rest of the Look

The 22-year-old completed the look with a stunning but perhaps not school dress code compliant beaded chartreuse micro mini dress, white knee socks, and similarly prep school-coded green ballet flats, all by Miu Miu.

Melissa Hernandez handled makeup, adding a slight wing to Rodrigo’s black liner and touch of natural-looking blush.

Okay, okay, class dismissed. There’s no homework, but anyone who can tell me when Rodrigo’s third album is coming gets extra credit.