Olivia Rodrigo’s latest street-style moment is a nostalgic take on ’90s grunge, with her outfit looking straight out of 10 Things I Hate About You.

The “Love Is Embarrassing” singer stepped out with friends Conan Gray and Madison Hu in New York City on Sunday. For the occasion, she dressed in a low-key look composed of a vintage ’90s graphic T-shirt paired with a green plaid miniskirt, ripped sheer black tights, white ankle socks, and Mary Jane loafers from Dr. Martens.

Rodrigo stayed warm with a black single-breasted wool coat from Acne Studios, and rounded out the outfit with an array of designer accessories, including Khaite sunglasses and and a black leather JW Anderson crossbody bag, which she simply slung over one shoulder.

Rodrigo is in the midst of the Guts World Tour following the release of her Grammy-nominated sophomore album, Guts, last September.

“I took quite a long time making this record, Guts. It took maybe a year or a year and a half of truly working on it,” she said in an interview with The New Yorker last year. “And I had a lot of reservations when starting out the album-making process. Coming off of the very unexpected, very appreciated success that [debut album] Sour had, there was so much pressure on what would come next. I had all these voices in my head—what I thought people would like, not wanting to let people down. And so it took me a while to get to a place where I finally felt like I could be creative and just start writing songs that I wanted to hear on the radio, which should always be your paramount focus when you’re making anything.”

As an associate editor at HarpersBAZAAR.com, Chelsey keeps a finger on the pulse on all things celeb news. She also writes on social movements, connecting with activists leading the fight on workers' rights, climate justice, and more. Offline, she’s probably spending too much time on TikTok, rewatching Emma (the 2020 version, of course), or buying yet another corset.