The world first met Taylor Swift at the tender age of 16, with the release of her self-titled debut album. Notable for making her the youngest person to single-handedly write and perform a No. 1 song on the Hot Country Chart (for "Our Song," the album's third single), the album presented an artist who was firmly entrenched in the world of confessional country music. The lead single was named after Tim McGraw, after all.
Owing to her tender age and her genre trappings, Taylor's look at the start was cutesy cowgirl chic and her hair was all about celebrating those natural cascading curls.
Two years after her auspicious debut, Taylor was back with her next album. And with Fearless, we got our first indication that this career wouldn't stay pure country for very long. Already, the sound has greater pop influences and lead single "Love Story" becomes the first major crossover hit of her career, becoming one of the best-selling singles of all-time internationally. The album is not only the best-selling album of 2009 (making the youngest artist ever to earn that distinction), but it became the most-awarded album in history of country music, earning Album of the Year at the Academy of Country Music Awards, the Country Music Association Awards, the American Music Awards, and the 52nd Annual Grammys, where she becomes the youngest person in the history of to ever win the award.
As seen on both the cover and here, during the Fearless Tour, Taylor's style began to mature as she prepared to leave her teenage years behind. Her natural curls were still a main focal point—the girl could toss them like nobody's business—but there's a hint of glam creeping in everywhere else, from the glitter on the guitar to her chic dresses. She's still rocking the boots as a nod to her roots, though.
By the time her third album was released in 2010, Taylor was teetering into superstar territory. The infamous Kanye West moment at the VMAs had happened the year prior, she'd had some high profile relationships (Joe Jonas, John Mayer) come and go, and she wasn't afraid to nod to all of it in her lyrics. Sonically, we're still in country-pop territory, but with some orchestration and pop-punk influences added into the mix for the first time. With over a million copies sold in its first week, Speak Now lands Taylor the fifth-biggest debut in history for a female artist.
Stylistically, Speak Now is a stop-gap era for Taylor. She's gotten a bit more glam by this point, but she hasn't done much to drastically shake up her look. But it's coming soon.
Inspired by "the kind of tumultuous, crazy, insane, intense, semi-toxic relationships that I've experienced in the last two years" and the emotions they caused her, Red marks Taylor at her most transitional. While ostensibly still a country album, you'd be hard-pressed to find anything that fits purely in that genre of music. Here, she begins working with pop music impresario Max Martin for the first time, creating massive crossover hits like "I Knew You Were Trouble," "22" and "We Are Never Ever Getting Back Together" in the process. Released two months before the end of 2012, Red still managed to become the second best-selling album of the year, with it earning Taylor the distinction of the third-biggest debut for a female artist ever. (For those keeping score, she now has two albums in that top five.)
And it's here that her look gets the biggest overhaul yet. Gone are her natural curls and in their place are some of the breeziest beach waves we've ever seen, along with a blunt bang. And while a lot of people thought she'd begun straightening treatments to calm those curls, she revealed in the April 2019 issue of Elle that that wasn't exactly the case. "From birth, I had the curliest hair and now it is STRAIGHT," she told the magazine as she detailed all the things she'd learned in her first 29 years on the planet. "It's the straight hair I wished for every day in junior high. But just as I was coming to terms with loving my curls, they've left me. Please pray for their safe return." She also began to embrace a retro-cool hipster vibe that involved a lot of black hats and men's style dress shoes. It was like Brooklyn became the biggest pop star in the world and we loved it.
Nearly a decade into her career, Taylor shook it off, alright. With the release of 1989, she had finally completely shed the trappings of country music and went full-blown pop. With Max Martin on board as the album's co-executive producer, sharing the title with her, she embraced the synth-pop sound of her birth year and gave us bop after bop. (Seriously, find us a bad song on 1989. We'll wait.) The album makes her the first artist to achieve three million-selling albums within the first week of release and also earns her second Album of the Year win at the 58th Grammy Awards, making her the first female solo artist to win the category twice.
With her hair the shortest it had ever been, 1989 also saw Taylor go full-blown pop diva in the style department. On her killer world tour, which saw her bring out a new member of her squad each night to share the stage, she embraced crop tops, plenty of color, and a sleekness that hadn't been present thus far. This was Taylor Swift, the woman. And she was here to roar.
The first album to break her previous release pattern of every two years, reputation saw Taylor tackle, well, her reputation head-on. Shifting again into the realm of electro-pop, the album is darker and more dance-oriented anything she'd ever done and it marked a new beginning for Taylor. RIP Old Taylor who can't come to the phone. Once again proving she's one of the biggest forces in music, the album is only released in November and still goes on to become the best-selling album of the year in America.
To go along with the edgy, darker tone of her music, Taylor adopted a radical new look. Embracing an accompanying snake motif and killing off all her old personas in that first video for "Look What You Made Me Do," the new Taylor rocked a lot of black and a darker red lip that all telegraphed the idea that she wasn't taking anyone's crap anymore. It was powerful and edgy, without totally sacrificing her trademark femininity. And it wouldn't last too long.
While we've only got one song to go off of for this new album era, "ME!" finds Taylor returning to the sweeter side of life. The track, a true collaboration with Panic at the Disco frontman Brendon Urie, is an ode to individuality and self-acceptance and has us feeling that Taylor successfully exorcised all her demons with reputation. As a sign of what's to come, it seems as though Taylor is all smiles this time around.
The first indicator that this new era was something a bit lighter was Taylor's look at the TIME 100 Gala, when she stepped out in this fairy-tale J. Mendel gown, looking like a strawberry lemonade sherbet princess. The billowing sleeves hint at a sense of irony about the aesthetic, one that's played up in the "ME!" video as well. If she's going back to her America's sweetheart roots, she's going to have some fun with it at least.