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.


(Image credit: The Image Direct)

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

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

Allyson Payer
Senior Editor

Allyson is a senior editor for Who What Wear. She joined the company in 2014 as co-founder Katherine Power's executive assistant and over the years has written hundreds of stories for Who What Wear. Prior to her career in fashion, Allyson worked in the entertainment industry at companies such as Sony Pictures Television. Allyson is now based in Raleigh, North Carolina, and is originally from Baton Rouge, Louisiana. She holds a BFA in theater. Her path to fashion may not have been linear, but based on the number of fashion magazines she collected as a child and young adult, it was meant to be.