Olivia Rodrigo Toughened Up Her Tiny Linen Short Shorts With Unexpected Summer Boots

Olivia Rodrigo knows her way around the wrong shoe theory, but her latest look took the styling trick to a whole new level.

Prior to her Governors Ball performance on June 7, the 22-year-old pop star was photographed out in wearing a very on-brand pair of shorts in New York City. Known for rocking polka dots dresses when she’s not sporting denim shorts or sparkling hot pants, Rodrigo combined her style signatures with a pair of white linen short shorts with a dainty black polka dot print.

She paired the summery shorts with a black tank top and slouchy black tote with silver hardware, giving the feminine pattern even more edge with her black manicur manicure and beaded lizard bag charm. (Yes, Gen Z has officially adopted the millennial summer camp craft as part of their aesthetic.)

But if that didn’t give the look enough “Brutal” energy to contrast the “Lacy”-esque shorts, the singer added a non-seasonal pair of black leather boots to tie everything together.

Lo and behold, this look was filled with easter eggs for her Governers Ball performance later in the evening. For her set, Rodrigo traded her linen short shorts for an even shorter pair of red hot pants with silver studs—which definitely still count as polka dots —and a matching red bustier. She even kept on her leather calf boots, giving “day to night” dressing a whole new meaning.

Olivia Rodrigo at the 2025 Governors Ball Music Festival held at Flushing Meadows Corona Park on June 07, 2025 in New York, New York. (Photo by Nina Westervelt/Billboard via Getty Images)Nina Westervelt/Getty Images