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

<p>Raymond Hall/GC Images</p> Taylor Swift wears $34 hat in New York City

Raymond Hall/GC Images

Taylor Swift wears $34 hat in New York City

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 gameBlake 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."

<p>Raymond Hall/GC Images</p> Taylor Swift steps out in $34 hat in New York City

Raymond Hall/GC Images

Taylor Swift steps out in $34 hat in New York City

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.

<p>Raymond Hall/GC Images</p> Taylor Swift in New York City on Oct. 26

Raymond Hall/GC Images

Taylor Swift in New York City on Oct. 26

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!)

<p>BlayzenPhotos / BACKGRID</p> Taylor Swift and Blake Lively

BlayzenPhotos / BACKGRID

Taylor Swift and Blake Lively

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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