Taylor Swift Pairs a $35 Hat and Stella McCartney Dress with Boots From Her “1989” Era

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Swift was spotted wearing the preppy ensemble as she hung out with Blake Lively, Ryan Reynolds and Hugh Jackman on Thursday

Taylor Swift is firmly back in her 1989 era.

Ahead of Friday’s release of 1989 (Taylor’s Version), Swift, 33, was spotted entering a brownstone in New York City with close pals — and fellow visitors to the box at the Jets/Chiefs game — Blake Lively, Ryan Reynolds, Hugh Jackman and Shawn Levy (who made a cameo in the 10-minute version of her “All Too Well” music video). 

For the occasion, the Grammy winner wore a preppy, oversized black polo shirt from Stella McCartney paired with a $2,525 leather micro TOD’s bag (last seen on her girl's night with Selena Gomez and Zoë Kravitz), and oxblood leather knee-high boots. She completed her look with an affordable $35 hat from Polo Ralph Lauren. Around her neck was a choker with a small heart pendant that appeared to read "MOM."

Longtime Swifties quickly clocked the possible 1989 Easter eggs included in her outfit, starting with her boots, which closely resemble a pair she was often seen wearing in 2015. Additionally, the “Anti-hero” singer favored TOD’s purses during her first 1989 era, too. 

Swift’s outfit wasn’t all about 1989 though. In 2019, she collaborated with McCartney on a line of merch inspired by her fourth studio album, Lover.

Related: Taylor Swift and Selena Gomez Twinned in the High-Rise Jean Style That's Here to Stay — Similar Pairs Start at $10

The singer-songwriter’s get-together with friends marks the latest example of her embracing a preppy cool look in recent months. Part of her current style choices likely comes from her preparing to re-release 1989, but it could also be a result of her embracing casual game day looks since she began seeing Kansas City Chiefs tight end Travis Kelce.

Last Sunday, Swift wowed fans in a vintage Kansas City Chiefs sweatshirt and pleated miniskirt as the Chiefs took on the Los Angeles Chargers. The week before, she rocked a red, black and white Chiefs windbreaker from Erin Andrews.

Swift isn’t just showing off her collegiate style on game days though. In early September, she wore a navy blue polo shirt with jean shorts, and that same month, she was also spotted wearing a gray pleated miniskirt to an album release party in New York City. (And let's not forget the New York University sweatshirt from the spring!)

Swift was once again in perfect style sync with her pals; Lively, 36, was also giving off major casual fall vibes on Thursday.

The Rhythm Section actress wore a cozy beige gray cardigan over a ribbed top paired with light-wash mom jeans and gold-framed sunnies. She completed her ensemble with a pop of color from her quilted blue purse. 

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