Looking back at Taylor Swift's ‘1989’ era, from the outfits to her dating history

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Taylor Swift is taking listeners back to her "1989" era with the release of "1989 (Taylor's Version)" Oct. 27 — and by "1989," we mean 2014, when the album came out. Swift was 24 years old at the time.

Swift reflected on that time in her life in the 12-paragraph prologue accompanying the album. She said "1989" followed a time of complete "reinvention" for her, starting with her drastic haircut and extending to the city she called home and the sound of her music.

"How does a person reinvent herself, you ask? In any way I could think of. Musically, geographically, aesthetically, behaviorally, motivationally ... and I did so joyfully," Swift writes in the prologue.

Swift's albums are associated with eras, each with a distinct sonic personality, outfits, aesthetics, lyrical themes and romantic inspirations (because while Swift rarely speaks about her dating life in interviews, she does sing about it).

The "1989" era was marked by New York views, girl squad hangouts and seagulls — lots of seagulls.

In the prologue, Swift wrote her friend group photos were also her strategy to deflect the "slut shaming" she said she experienced in the years prior. Instead of dissipating speculation about her love life, she wrote that it created more, in a paragraph that seems to address rumors about her sexuality.

“Being a consummate optimist, I assumed I could fix this if I simply changed my behavior. I swore off dating and decided to focus only on myself, my music, my growth, and my female friendships. If I only hung out with my female friends, people couldn’t sensationalize or sexualize that — right? I would learn later on that people could and people would,” she wirtes.

Her fifth studio album is also known for its full-on shift to pop with an homage to 1980s synth sounds. While Swift began as a country artist, her music became more pop-infused with each album released in the lead-up to "1989."

With five new vault tracks coming out Oct. 27, fans are preparing to look back at a snapshot of Swift's life through a new lens. Here's a review of the "1989" era and what Swift was up to in the years 2012, 2013 and 2014.

What is '1989' about?

"1989" explores the feelings that come after a major move or life change. The songs focus on a young woman exploring freedom (“Welcome to New York”), fun (“Shake It Off") and flirtation (“How You Get the Girl”).

The songs aren't about lasting love — but they are about exhilarating and enlightening love. Many of the romantic songs follow life after a relationship has ended: "Clean" is about gaining closure after a breakup, "I Wish You Would" is about regret, "Bad Blood" is about a dead end. Others, like "Wildest Dreams," are about affairs the singer knows won't last.

In "Blank Space," one of the most popular tracks off the album, Swift also plays with her reputation as a serial dater with a wink through the chorus, "Got a long list of ex-lovers/ They’ll tell you I’m insane/ But I’ve got a blank space, baby/ And I’ll write your name."

Welcome to New York!

Swift moved to New York in early 2014, and her connection to the city is all over the album — most obviously in the opening track, "Welcome to New York."

“I wanted to start the album with this song because New York has been an important landscape and location for the story of my life in the last couple of years," Swift said in a YouTube video she shared in 2014 talking about the track. "I dreamt about moving to New York. I obsessed over moving to New York, and then I did it."

Celebrity Sightings In New York City - June 27, 2023 (Gotham / GC Images)
Celebrity Sightings In New York City - June 27, 2023 (Gotham / GC Images)

She said the city inspired the sound and the theme of the whole album.

“The inspiration I found in that city is kind of hard to describe and hard to compare to any other force of inspiration I’ve ever experienced in my life,” she said in the video. “It’s like an electric city.”

Swift and her girl squad

Her "1989" era was marked by Swift's outings with her friends. Selena Gomez and Gigi Hadid are two of the many who made appearances with Swift at the time and are still seen with her today.

A roundup of her girl squad can be seen in the music video for "Bad Blood," featuring Kendrick Lamar.

The list of features on the video include many well-known names, including Gomez, Hadid, Hailee Steinfeld, Zendaya, Jessica Alba, Mariska Hargitay and Ellen Pompeo.

Friendship with Karlie Kloss

Fans who remember Swift's "1989" era inevitably also recall the close friendship between Swift and model Karlie Kloss.

Kloss and Swift were so close they had a nickname, Kaylor. The model and the singer first met in 2013 after a Victoria Secret fashion show, Swift told Vogue.

The two were inseparable — then they separated, or seemed to. Following a highly publicized friendship between 2013 and 2015, the two have not been seen in public together since 2016. Neither has commented on rumors of their friend breakup.

However, Kloss has dispelled rumors of a feud, saying in a 2018 video interview with Vogue, “Taylor and I are still really good friends.”

2014 American Music Awards -  Backstage And Audience (Kevin Mazur / AMA2014 / Getty Images)
2014 American Music Awards - Backstage And Audience (Kevin Mazur / AMA2014 / Getty Images)

Nonetheless, fans were shocked to see Kloss at the last show of the first North American leg of the “Eras Tour,” where Swift announced “1989 (Taylor’s Version).”

Swift did not attend either of Kloss' two weddings to Joshua Kushner.

The classic '1989' outfit? Short hair and sunglasses

When you think "1989," think bob. She cut her hair around 2014 and styled it into a chopped lob almost 10 years later for the "Eras Tour" concert film premiere.

Red lipstick is another staple for Swift and is featured in "1989" art. Some of her other "1989" outfit staples have stayed in 2014, though, like the sunglasses.

Who was Swift dating back then? Songs were inspired by Harry Styles

Swift's relationship with Harry Styles was no secret. The young couple, often dubbed "Haylor," is still talked about to this day. For example, their brief reunion at the 2023 Grammy Awards sent Twitter spiraling.

Celebrity Sightings - Bauer-Griffin - 2012 (David Krieger / Bauer-Griffin / GC Images)
Celebrity Sightings - Bauer-Griffin - 2012 (David Krieger / Bauer-Griffin / GC Images)

The two dated for a few months in 2012, back when Styles was still part of the boy band One Direction.

Fans think their relationship bled into "1989," most notably in the track "Style," which seems to riff off his last name.

While she hasn't confirmed who the song is about, she has explained the story behind the relationship discussed in the lyrics.

"It’s basically one of those relationships that’s always a bit off. The two people are trying to forget each other, they both have been out with other people and are trying to forget one another. So, it’s like, ‘Alright, I heard you went off with her and you came back, and well, I’ve done that, too,’” Swift said in a 2014 interview with Ryan Seacrest.

She also said the song "sounds like that feeling felt."

"I love it when a sound of a song matches up with the feeling that inspired it," she said.

The reference to "paper airplanes flying" in "Out of the Woods" also seemed to be a nod to Swift and Styles wearing paper airplane necklaces.

Years later, Styles seemed to refer to their relationship in his track "Two Ghosts," with lyrical ties to "Style."

The lines "same lips red, same eyes blue" and "same white shirt, couple more tattoos" in Styles' track closely relate to Swift's lyrics "I got that red lip classic thing that you like" and "You got that long hair, slicked back, white T-shirt."

This article was originally published on TODAY.com