Olivia Rodrigo Proves a Pleated Skirt, Graphic Baby Tee and Loafers Are the Best Fall Outfit While It’s Still Hot Out

The singer and actress loves a good ’90s-inspired look.
Olivia Rodrigo.

Olivia Rodrigo.


Olivia Rodrigo is our latest fashion icon and she’s constantly pulling from stylish, comfortable and classy ’90s trends. The “drivers license” singer, who dropped her highly-anticipated sophomore album, GUTS, on Sept. 8, was spotted in New York City earlier this week wearing a fun sporty look. The 20-year-old donned a white graphic baby tee with a woman’s face printed in red and a pleated white micro tennis skirt. She completed the look with ankle crew socks and sophisticated black keyhole loafers, a chunky statement ring and a bold red-orange lip. Her long brown locks were smooth and loosely curled at the ends.

The three-time Grammy Award winner and California native wore the outfit to the SiriusXM broadcasting studio on Sept. 6

The High School Musical: The Musical: The Series star, who has six Video Music Award nominations this year for her July-released single “Vampire,” is set to perform at the event on Sept. 12. 

Olivia Rodrigo.

Olivia Rodrigo.

“There’s a sort of wide-eyed innocence to the first album that lots of people picked up on, and I kind of freaked out this time being like, ‘Oh my god, I don’t have this 17-year-old heartbreak that everyone’s had. My life is different now.’ This sounds weird to say, but I think over time, I’ve realized that I’m really not that special,” Rodrigo said about how this album differs from her overnight-viral debut, Sour. “My life is just so—I was home-schooled and all of this stuff happened in my career, but then I really boiled my problems down and I’m like, ‘Oh, they’re just 19-year-old, 20-year-old problems in a different environment.’ If you speak honestly about any experience, then someone is going to find truth in it.”

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Ananya Panchal
ANANYA PANCHAL

Ananya Panchal is a writer on the Lifestyle and Trending News team for SI Swimsuit, where she covers fashion, beauty, pop culture and the internet’s favorite personalities and trends. She joined the brand in 2022 after roles at Bustle, the San Francisco Chronicle and the TODAY Show. Panchal loves to write about fashion in all its forms—from standout runway moments and evolving street style to the best accessories to elevate each season’s wardrobe (she rarely goes anywhere without a stack of jewelry and a coffee in hand). A self-proclaimed beauty fanatic, she’s always on the hunt for must-have products and loves breaking down viral trends. Her favorite series at the moment is spotlighting female founders and the stories behind the brands they’ve built—especially those shaping the future of fashion, wellness and tech. She is based between New York City and San Francisco and, when she’s not writing, can be found rewatching One Tree Hill, playing sudoku, trying new restaurants or ranking her favorite Disney Channel Original Movies. She holds a bachelor’s degree in communications and journalism with a minor in criminal justice from Boston University.