Olivia Rodrigo always understands the assignment.
On Friday, January 19, the singer enjoyed a girls night out watching the Los Angeles Lakers take on the Brooklyn Nets alongside BFF and fellow entertainer, Tate McRae.
In true Rodrigo fashion, the "bad idea right?" singer rocked her signature preppy look, wearing a simple black vest over a plain white tee. She paired the chic ensemble with a short black miniskirt, white ankle socks, and large black, lace-up loafers.
For a bit of feminine flair, Rodrigo wore small jeweled earrings, a quartz bead bracelet, several dainty silver rings, and a small black purse. To complete her '90s preppy vibe, Rodrigo stuck to minimal makeup in the form of her signature black winged eyeliner and a soft red lip.
Rodrigo is known for her throwback fashion sense, often wearing '90s and early-aughts fashion pieces.
In the wake of her Saturday Night Live performance in December 2023, Rodrigo wore a Y2K-like outfit featuring a fuzzy green crop top and low-rise pants.
She singer paired the end-of-the-world-inspired top with a pair of black, closed-toe platform stiletto pumps in black suede and a sleek patent leather shoulder bag.
And at the 2022 Grammys, Rodrigo stunned in a '90s-Meets-Gen-Z look, featuring a breathtaking black and pink, punk-inspired gown by Vivienne Westwood and the ultimate nod to the '90s: Black and pink sparkly chokers.
In an interview with British Vogue, Rodrigo told the publication that she tires to "shop vintage, mostly."
“I love a Depop or The Real Real purchase,” she told the publication at the time. “I look for quality, and I like pieces that are kind of funky and weird.”
Sustainability also plays a major role in Rodrigo's fashion choices. In an interview with Schön! magazine, the entertainer revealed that she watched the documentary The True Cost on Netflix, which introduced her to the concept of sustainable fashion.
"If you haven't seen it, you should totally check it out," she told the publication at the time. "At the time, I was starting to think about how my personal actions affected our environment for the first time. It's sort of a scary thing to be 14 and realize your generation is nearing tipping points for irreversible damage to the planet."
Rodrigo went on to say that until she watched the documentary her "favorite thing was to go to the mall and buy clothes that were way too cheap and wear the item once."
"I realized I couldn't keep up those habits if I truly cared about the planet," she continued. "The fashion industry is also notorious for taking advantage of women and children in less-developed countries. All that to say, I've spent the last few years trying to keep my clothing consumption as sustainable as I can."
We stan a '90s fashion-loving, environmentally conscious queen!