Fans expect to see her in Kansas City at the Chiefs game on Sunday, New Year’s Eve, since she took her immediate family — mom, dad and brother dressed as Santa — to that unfortunate game on Christmas Day. Maybe, just for grins, she’ll wear a costume? On Dec. 31, 2018, Swift, known for hosting great parties, threw what is still discussed as an “epic” New Year’s party at her New York City home. The party came after a two-year drought in which the singer did not post any photos of her famous, celebrity-studded Fourth of July parties at her Rhode Island mansion.

“The parties were famously splashed across Instagram in a choreographed display of #content. So when we were deprived of the party in 2017 and again in 2018, we assumed the hostess with the most had stopped, well, hosting,” Vogue wrote on Jan. 1, 2019. “But lucky for us, that all changed on New Year’s Eve, when Swift hosted a dress up party to ring in 2019 and flooded our feeds with new photos of her friendship circle.” For the costumed affair, Swift donned a Little Mermaid costume, wearing a red wig and a lobster-shaped purse slung around her neck.

“Mary Poppins, Audrey, Ariel, Ms. Frizzle, Cinderella, Gwen, Mr. Toad, Avril, Nancy Drew, Posh Spice, Rizzo, Frida Kahlo, Steve Irwin, Dorothy,” she wrote on Instagram. “This new year we decided to dress up as our childhood heroes. “Sending you all love and hope going into 2019.”

Swift’s BFF Blake Lively, dressed as that Dorothy girl from Kansas, was there. Squad member Gigi Hadid went as Mary Poppins. Lively’s husband, Ryan Reynolds, was in a suit and tie dressed as … himself?

Two years later, as the world lurched into 2021 after the first year of the pandemic, Swift’s mood matched the moment and she climbed inside a furry brown bear costume with big, scary teeth to kick 2020 to the curb. “Bye 2020, it’s been weird,” she wrote on Dec. 31, 2020, to her Instagram followers, nearly 4 million of whom “liked” the quirky adieu.

New Year’s Eve can leave a person feeling downright bittersweet or bitter. We’re not sure which it was for Swift on New Year’s Eve in 2008, but we can make an educated guess. She performed on “Dick Clark’s New Year’s Rockin’ Eve With Ryan Seacrest.” It’s part of Swift infamy because the Jonas Brothers performed that night too — and she and Joe Jonas had just gone through a messy, headline-making breakup. Something something about him breaking up with her during a 27-second phone call. E! News called the show “the most awkward New Year’s Eve TV moment of all time.”

That night Swift sang one of the songs the breakup inspired — “Forever & Always” from her “Fearless” album. Fast forward to 2017 and Swift embraced the hope of the holiday in her song “New Year’s Day,” the closing track on her sixth studio album, “Reputation.” Reviews like this one in Glamour magazine described it as “the most lyrically poignant song on the record.”

“The majority of Reputation features Swift lamenting about love, drinking, and settling scores over large, bombastic beats — but not ‘New Year’s Day,’” Christopher Rosa wrote. “Here, she talks about the aftermath of a wild New Year’s Eve — the bottles on the floor, girls walking with their heels off — and how she’s lucky to have someone to help her navigate the next day. “It’s not about partying and fun anymore; it’s about beginning the next chapter of her life with a clean slate.” There’s glitter on the floor after the party Girls carrying their shoes down in the lobby Candle wax and Polaroids on the hardwood floor You and me from the night before Fans, though, know that “New Year’s Day” is another song tinged with heartache.

Swift has said she was inspired by a special moment she shared with her then-boyfriend, British actor Joe Alwyn, her last long-term relationship before Kelce. ”We threw a big New Year’s Eve party in London this year, and I was thinking about how everybody talks and thinks about who you kiss at midnight. Like it’s this big romantic idea of like, ‘Who are you gonna kiss at midnight, like ring in the new year.’ And I think that is very romantic,” she told fans at an iHeartRadio release party for “Reputation.” “But I think there’s something even more romantic about who’s gonna deal with you on New Year’s Day. Who’s willing to give you Advil and clean up the house? I think that states more of a permanence. So I was thinking about that, and I wrote this song called ‘New Year’s Day.’” The hit was the final “surprise song” of the U.S. leg of her Eras Tour this year. It was around that time she and Kelce started secretly hanging out.