Taylor Swift is seen in the West Village on October 26 2023

Taylor Swift’s prep-school-inspired fall wardrobe just got a lot more daring.

On October 26, the 33-year-old pop star was photographed in New York City’s West Village with Deadpool 3 director (and Chiefs-Jets suite attendee) Shawn Levy. In the snaps, Swift can be seen wearing Stella McCartney’s oversized Pony Club rugby top with her favored Ralph Lauren baseball cap, a camel-colored Tod’s mini satchel, and some rich reddish-brown riding boots (the 2010s are truly back, baby). The oversized “jumper” (read: this is not a shirtdress) retails for $850 and runs from XXS to XL.

This look says, “I grabbed my boyfriend’s shirt on my way out the door,” in the chicest way possible, even though it surely came from Swift’s own closet. Of course, her loose blonde waves, orange-red lip, and refined accessories give the ensemble a polished finish, practically screaming quiet luxury.

Taylor Swift is seen in the West Village on October 26, 2023

Raymond Hall

Taylor Swift was pretty far down on my list of celebrities expected to embrace the ongoing pantsless trend, but she truly showed us all how it’s done. She doesn’t even seem to be faking the aesthetic with short shorts or a tights-as-pants moment. Later in the day, she removed the hat—fully showing off her famous bangs and solidifying this look as her best of the season.

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