Olivia Rodrigo Is in Her Preppy School Girl Era With Latest Mini Dresses

The pop star leans into a school girl aesthetic with these stylish looks.

Olivia Rodrigo attends the 2025 Vanity Fair Oscar Party in Beverly Hills, California in March 2025. / Phillip Faraone/VF25/Getty Images

Olivia Rodrigo is taking her fans back to school with her latest preppy looks. The singer-songwriter put her spin on a classic style with various accessories that not only spruced up her dresses but also could serve as a hint of what theme her upcoming era will follow.

Rodrigo took to Instagram to post snaps of three lovely outfits. The first consisted of a black short-sleeved collared dress with a circle skirt. She paired this with black sunglasses, a red purse and black over-the-ear headphones. Her dark red puffer iPhone case made an appearance for this ‘fit as well, adding a pop of color.

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For her second outfit, the black headphones showed up once more, complementing a pale blue plaid dress. She opted for black dress shoes and a black purse as accessories.

Last but certainly not least, Rodrigo finished off the school girl aesthetic post with a red, white and blue look. Her navy blue cardigan was ultra chic, even more so when she styled it over her burgundy plaid dress. And, of course, the black headphones made this bathroom selfie worth a double tap on the screen.

The inclusion of the color red in this post has fans raising eyebrows. Red has been popping up throughout her social media posts, including her birthday celebration post in February. Her fans are convinced that her third studio album will have some sort of red theme, especially after hearing her “In the Bag” video with Vogue.

“I have a Pinterest board full of all the bags that I want,” Rodrigo shared. “Beautiful red—deep red Chanel ones. I have my eye on those and I’m waiting for the right one. It has to be the right size and the right color. And I don’t like gold. I never wear gold, so all of the hardware has to be silver.”

She added, looking amongst a sea of her mostly red items, “Yeah, I love red. It’s my new favorite color.”

Although there’s no word on when her third album is coming up, fans believe they may have cracked a code ahead of the release.

“yeah 0r3 will be red,” one fan wrote underneath a post compiling Rodrigo’s new love for red.

“ohh so she was teasing that with her red bra for guts (spilled) cover,” another fan pieced together.

“RED IS GONNA EAT FOR OR3,” one fan exclaimed.

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