Olivia Rodrigo Wore the Chic Basic That Instantly Upgrades Skinny Jeans

Gen-Z queen Olivia Rodrigo just did the unthinkable and wore skinny jeans (I apologize for the hyperbole). It’s not something we’re used to seeing the Y2K-loving musician wear. But rumor has it that skinny jeans are coming back with a vengeance in 2023, so perhaps she’s getting a head start.

The outfit I’m referring to is one Rodrigo wore while out this week in NYC. She paired the aforementioned skinny jeans with a ribbed gray sweater and her go-to Converse Chuck Taylor high-tops. What took the outfit from cool to chic was the addition of a leather blazer, a trend that’s been percolating for several seasons now. Having polished basics that go with everything (like a leather blazer) is key because you can wear them with easy, casual pieces and look like you made an effort every single time.

Scroll to shop Rodrigo’s casual-chic look, along with some of my favorite leather blazers on the market.

On Olivia Rodrigo: Converse Chuck Taylor All Star High Top Sneakers ($65)

Next up, the best winter shoes to wear with skinny jeans.