Taylor Swift Broke a Long-Standing Fashion Rule Twice in One Outfit

Taylor Swift’s new style era may be prep-school-inspired, but that doesn’t mean she’s a teacher’s pet.

Okay, that was cheesy, but her latest look was anything but. On the evening of the 1989 release, the 33-year-old pop school stepped out in New York City wearing an ensemble that fits perfectly into her light academia aesthetic while breaking a longstanding fashion rule. Swift styled a black top with not one but two brown-toned pieces: a rich leather blazer and a corduroy miniskirt. She brought the whole thing together with her signature red lip, a pair of rich burgundy ankle booties, and gold accessories—including mismatched, asymmetrical earrings for an added touch of rebellion.

Taylor Swift is seen in the West Village on October 27, 2023.


This comes one day after Taylor Swift embraced the no-pants trend during a supposed visit to Bradley Cooper’s home in the West Village. Though Swift’s close friend (and Cooper’s rumored girlfriend) Gigi Hadid was not photographed, Swift was spotted arriving with Deadpool 3 director Shawn Levy and leaving around the same time as Blake Lively. Interesting!

In the photos, Swift could be seen wearing Stella McCartney’s oversized Pony Club rugby top—which is now largely sold out—with her favored Ralph Lauren baseball cap, a camel-colored Tod’s mini satchel, and reddish-brown riding boots. Styled like a true woman of the 2010s!

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