Relive the Biggest Moments From Taylor Swift's Red Era, From Maple Lattes to "Haylor"

We don't know about you, but we're feeling super nostalgic over the release of Taylor Swift's rerecording of her 2012 album Red, so we're looking back on that era of her life.

By Tierney Bricker Nov 12, 2021 12:00 PMTags
Watch: Taylor Swift Teases New Short Film for "All Too Well"

No, we are not well.

Taylor Swift fans, the time has finally come to begin again, with the superstar's rerecorded version of her 2012 album Red dropping on Nov. 12. We don't know about you, but we're feeling all the feels like they are brand-new thanks to her updated takes on classic such as "I Knew You Were Trouble," "We Are Never Ever Getting Back Together," and, of course, "All Too Well," her epic ballad about her romance with Jake Gyllenhaal

Returning to Red, Swift's fourth studio album released when she was just 22 years old, felt whimsical and nostalgic—or dare we say "happy, free, confused, and lonely in the best way"?—and had us reminiscing about that era of the singer's storied career. The scarves, the lattes, the clapbacks, the rise and fall of "Haylor," we remember it all, all, all...too well.

Taylor Swift's Cutest Cat Photos

Remembering Red comes in flashbacks and echoes, tell ourselves it's time now, gotta look back on all of Swift's biggest moments from that era.

Burning Red

The year before Red's debut, Swift teased her fourth studio album in an interview with Vogue

"There's just been this earth-shattering, not recent, but absolute crash-and-burn heartbreak," she said, "and that will turn out to be what the next album is about. The only way that I can feel better about myself—pull myself out of that awful pain of losing someone—is writing songs about it to get some sort of clarity."

And in 2020, when she reflected on the album with Rolling Stone, she admitted it was her "true breakup album. Every other album has flickers of different things. But this was an album that I wrote specifically about pure, absolute, to the core, heartbreak."

Swift was able to take that devastation and turn it into a declaration of her star power, with Red debuting at No. 1 and selling 1.21 million copies in its first week. Swift became the first artist since the Beatles—and the only female artist ever—to have three consecutive albums spend six or more weeks at No. 1 on the Billboard 200. Red also earned four Grammy nominations and its world tour grossed $150 million, becoming the highest-grossing tour by a country artist of all time.

Shutting Down Her Critics

So it might be hard to remember, but it was with Red that Swift's critics started writing her off as too "obsessed" with boys and labeling her as a serial dater, something she was definitely aware of.

"I'm sure if I looked up the latest Google Alerts rumor it would say I'm chasing somebody who doesn't like me as much as I like him," Swift told Elle in 2013. "People love that angle on me. They're like, 'Oh Taylor, coming on too strong again, chasing boys.' I never chase boys. They don't like it!"

But it was during her interview with Vogue the same year that she really fired back, calling out the misogyny within Hollywood and tabloid culture. 

"For a female to write about her feelings," she told the magazine, "and then be portrayed as some clingy, insane, desperate girlfriend in need of making you marry her and have kids with her, I think that's taking something that potentially should be celebrated—a woman writing about her feelings in a confessional way—that's taking it and turning it and twisting it into something that is frankly a little sexist."

That Golden Globes Moment

Let us set the scene for you: The year is 2013 and Tina Fey and Amy Poehler are hosting the 70th annual Golden Globe Awards. During one bit, the duo singled out the "We Are Never Ever Getting Back Together" singer for her seemingly endless boyfriends, and Fey joked, "You know what, Taylor Swift, you stay away from Michael J. Fox's son," then continued, "She needs some 'Me Time' to learn about herself."

Swift, who was a nominee but was not in the audience for the playful dig, was not amused by the shoutout, later telling Vanity Fair, "You know, Katie Couric is one of my favorite people because she said to me she had heard a quote that she loved"—from former Secretary of State Madeleine Albright—"that said, 'There's a special place in hell for women who don't help other women.'"

And she would go on to address why exactly the joke from Fey and Poehler crossed the line. 

"I was just sort of like, Oh well, you know, I can laugh at myself," Swift explained to Vogue. "But what it ended up adding to was this whole kind of everyone jumping on the bandwagon of 'Taylor dates too much'—which, you know, if you want some big revelation, since 2010 I have dated exactly two people."

And hey, if she were a man, as she would later sing on 2019's Lover, "They would toast to me, oh, let the players play. I'd be just like Leo, In Saint-Tropez."

But don't worry, there was no lingering bad blood between Swift and the hosting duo, with Swift and Poehler presenting an award together and showing off their comedic chemistry at the 2020 ceremony. 

Harry Styles Romance

Oh, Haylor. What a time.

Back in 2012, the Internet nearly combusted when it was reported that one of the world's biggest pop stars and the most popular member of One Direction were dating. The pair celebrated her 23rd birthday in London, they hit the slopes in Utah, they shared a New Year's Eve kiss in NYC and he met Swift's mom, Andrea. 

But after two months, Swift and Styles abruptly split in early 2013, with Swift later authorizing an anonymous friend to shed light on the breakup for Vogue

The situation was misreported in the media, the confidante insisted, and it was actually Styles who "chased" Swift for a year and "wore her down" before they began dating. But, the insider said, Swift initially ended their relationship when photos of Styles allegedly "making out" with someone while he was on tour in Australia surfaced online. 

Eventually, after Styles continued to pursue her, Swift got back together with him, "but the whole time she says she feels like he's looking at every girl and thinking about hooking up with every girl," the friend claimed, going on to say Styles basically ghosted Swift only to start texting her again. (Styles' rep at the time denied Swift's friend's account of the situation.)

Still, their shortlived romance lives on in infamy, thanks to several songs on 1989, including "Style," "I Knew You Were Trouble," and "Out of the Woods," which were reportedly inspired by the "Watermelon Sugar" singer. 

Styles weighed in on the songs in a 2017 interview with Rolling Stone, saying, "I mean, I don't know if they're about me or not…but the issue is, she's so good, they're bloody everywhere. I write from my experiences; everyone does that. I'm lucky if everything [we went through together] helped create those songs. That's what hits your heart."

And almost a decade after their relationship, Swift and Styles appear to be on friendly terms, with the famous exes sharing a candid moment at the 2021 Grammys, delighting Haylor fans. Glad to see they made it out of the woods!

The Jake Gyllenhaal Of It All

While they dated for a few months in late 2010, Swift remembered their relationship all too well, their shortlived romance reportedly inspiring many of the songs on Red, including "All Too Well," arguably her most lauded number.

It was the first song Swift wrote for the album after suffering for six months from writer's block caused by a breakup. "There's a kind of bad that gets so overpowering you can't even write about it," she admitted to USA Today.

It was also the "hardest" for her to write, with Swift telling Good Morning America, "It took me a really long time to filter through everything I wanted to put in the song without it being a 10-minute song, which you can't put on an album. I wanted a story that could work in the form of a song."

Other songs inspired by her split from Gyllenhaal include, "I Knew You Were Trouble," "Treachorous" and "We Are Never Ever Getting Back Together."

Swift would later reveal in an interview with New York that her ex called her after listening to the album and told her it was a "bittersweet experience." But did he keep that old scarf from that very first week? The world will never know...

The Start of a Beautiful Friendship

Swift performed at the 2013 Victoria's Secret Fashion Show, which is when she met supermodel Karlie Kloss, with the two becoming instant BFFs and once again sharing the stage at the lingerie brand's 2014 runway event.

They'd also go on to share the cover of Vogue in March 2015, inspired by their road trip to Big Sur.

"We were just like, 'You. My friend. Now,'" Swift told the magazine of their immediate connection. Kloss gushed, "You know, real friends are hard to find—and Taylor's a real friend. There's nothing better."

The pair were inseparable for years, but rumors of a falling-out ran rampant in 2018, which Kloss shot down at the time, telling The New York Times, "Don't believe everything you read."

Still, they have not been spotted together since that year and Swift was noticeably absent when Kloss married Joshua Kushner in 2019. But Kloss subtly supported Swift's 2020 album folklore, though fans are convinced a song on evermore is inspired by their allegedly fractured friendship. 

Reading Between the Lines

Arguably one of the most fun aspects of Red's rollout for fans were the hidden messages within the liner notes of the album, offering clues about each song's inspiration.

The most notable was, of course, was "MAPLE LATTES" in "All Too Well," which was a reference to the Thanksgiving date in which Swift and Gyllenhaal both ordered the autumnal beverage at a Brooklyn coffee shop. 

Other hidden messages include "WHEN I STOPPED CARING WHAT YOU THOUGHT" in "We Are Never Ever Getting Back Together," "I LOVE YOU DOESN'T COUNT AFTER GOODBYE" in "State of Grace" and "HYANNIS PORT" in "Everything Has Changed." More on the latter in a moment. 

The Kennedy Connection

Even before her brief romance with Conor Kennedy, the then-teenage son of Robert F. Kennedy Jr., Swift had a deep fascination with the famous family. 

"I'm just so obsessed with the whole history of J.F.K. and R.F.K," she told The New Yorker in 2011, adding she had read Laurence Leamer's 900-page The Kennedy Women. And, according to her 2013 Vogue profile, Swift's parents knew Rory Kennedy, Conor's aunt, which is how they met, and she accompanied Rory and his grandmother Ethel Kennedy to the Sundance Film Festival in 2012.

Soon after, Swift was invited to family parties at their home in Hyannis Port and she was photographed kissing Conor several times in the summer of 2012. She even received the ultimate blessing, Ethel saying they "should be so lucky," to have Swift one day becoming a member of the Kennedy dynasty.

Alas, their relationship was short-lived, with Swift and Conor calling it quits by the fall, though it did inspire the ballad "Begin Again" on Red, while Conor's grandparents' love story was the inspiration for "Starlight." 

Her Rhode Island Estate

In the spring 2013, Swift purchased her beachfront mansion in Watch Hill, reportedly paying $17.75 million in an all-cash deal after selling her Hyannis Port home earlier that same year. The property, which is known as High Watch, is "a rambling, white clapboard 1920s 'cottage' that sprawls atop the bluff that gives this town its name," according to The New York Times

It would also become the setting for many of Swift's infamous Fourth of July parties and the house would be the inspiration for her song "The Last Great American Dynasty," with the folklore tune telling the tale of the home's previous owner, socialite and philanthropist Rebekah Harkness.

"I got the house when I was in my early twenties as a place for my family to congregate and be together," Swift told Entertainment Weekly. "I was told about her, I think, by the real estate agent who was walking us through the property. And as soon as I found out about her, I wanted to know everything I could. So, I started reading. I found her so interesting.

She continued, "And then as more parallels began to develop between our two lives—being the lady that lives in that house on the hill that everybody gets to gossip about—I was always looking for an opportunity to write about her. And I finally found it."

Hey Girl!

In a truly adorkable moment, Swift guest-starred in a season two episode of Fox's hit sitcom New Girl

In a winking homage to her song "Speak Now," Swift played Elaine, the longtime love of Cece's fiancé Shivrang who ultimately elopes with him after their wedding is called off at the altar. 

"She was amazing. She's a fantastic actress. She did such a good job," the show's creator Liz Meriweather told E! News back in 2013. "Our set is a fun set to come to, but it's also a little bit crazy because there's a lot of improv and people shouting out extra jokes and she completely held her own and did such a great job with it. She fits in great."

In 2014, Swift also had a supporting role in the film adaptation of The Giver and received a "Best Original Song" nomination at the Golden Globe Awards for "Sweeter Than Fiction," the tune she co-wrote with longtime friend and collaborator Jack Antonoff for the One Chance soundtrack. 

The "Red" Look

Swift is known for changing up her fashion game for each album and Red proved to be her most autumnal. (Sure, folklore and evermore are also very fall-inspired, but dare we say the first is cottage-core while the latter is more wintery.) Think cozy scarves (including The Scarf), fitted peacoats, midi shift dresses and tights with boots all paired with a '70s-esque wispy bangs, straightened blowout and red lipstick, with the statement lip becoming a focal point of her 1989 look. Her accessory of choice was usually a coffee cup. 

A Peek Inside Wonderland

Pre-1989's famed listening parties held at Swift's various properties, fans were only given details of her whimsical home decor style courtesy of various magazine profiles.

When asked by Vanity Fair to describe her aesthetic, Swift answered, "Tim Burton-Alice in Wonderland-pirate ship-Peter Pan." 

Given a tour of her Nashville home, the writer offered crumbs, including that her foyer was "covered with frames of brightly colored paper flowers" and that "inside, you're greeted by a six-foot topiary rabbit." There were also " antique birdcages everywhere and mobs of crocheted throw pillows. There's a koi pond in the middle of the living room." We discover that she collects "old bottles, antique books, and precious little knickknacks" and that her bedroom was "white and fluffy."

Her walls were lined with photographs of her with her famous friends, including Emma Stone and Selena Gomez, and she also had a photo of the infamous moment at the 2009 MTV Video Music Awards when Kanye West interrupted her acceptance speech for best female video.

Red (Taylor's Version) is streaming now. 

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