Photos of Taylor Swift, Through the Years

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Taylor Swift has had as many reinventions as she’s had albums. While the singer first appeared on the music scene as a curly-haired teenager, she’s evolved into a true musical powerhouse. With nine albums under her belt, the singer-songwriter has managed to capture the attention and emotions of millions of fans. Once a country singer strumming an acoustic guitar, Taylor Swift has now veered into the worlds of electro-pop, alternative rock, and folk. Check out these pictures of the star throughout her celebrated career.

At 14 years old, Taylor Swift became the youngest artist to sign with Sony. However, she opted for the indie label Big Machine Records instead. Her early singles were true country songs, and with “Our Song,” the singer became the youngest person to write and sing a number one song.

Swift’s second album Fearless included classic songs like “Love Story” and “You Belong with Me.” This image of the singer is from the Fearless tour at Madison Square Garden in 2009.

During this era, Taylor Swift still embraced a country aesthetic. She was always seen with her classic tumbling blonde ringlets, and usually opted for fairytale-style dresses. In this picture, the “Back to December” singer is attending her very first Grammy Awards, in 2008.

Taylor Swift was nominated in the Best New Artist category, but lost out to Amy Winehouse. The Fearless tour ended up grossing over $63 million, and the three-part documentary — Journey to Fearless — was aired on TV.

The next time Taylor Swift showed up at the Grammys, she took home four awards. The singer won Best Female Country Vocal Performance, Best Country Album, Best Country Song, and Album of the Year. At the ceremony, Swift performed “You Belong with Me” and “Rhiannon” with iconic musician Stevie Nicks.

Around this time, the infamous Kanye West incident occurred. The rapper interrupted Taylor Swift during her acceptance speech at the MTV Video Music Awards, spawning years of memes, arguments, and rumors.

For the 2010 American Music Awards, Taylor Swift debuted straight hair, bangs, and cat-like eye makeup. She took home the award for Favorite Country Female Artist, and performed at the ceremony.

As well as writing and releasing her own albums, Swift also collaborated with other artists. She co-wrote and featured on “Half of My Heart” with John Mayer, and “Two Is Better Than One” with Boys Like Girls. The artist also contributed songs to Hannah Montana: The Movie and Valentine’s Day, both of which she also starred in.

Fans of Taylor Swift – known as Swifties – instantly recognize the singer’s iconic dress from the Speak Now tour. Swift wrote and co-produced every track on her third album, and it became the fastest-selling digital album by a female artist. Songs from this album include “Mean,” “Sparks Fly,” “The Story of Us,” and “Mine.”

Following the success of the Speak Now tour, the singer contributed two original songs to The Hunger Games soundtrack. At this stage in her career, Taylor Swift was only 20 years old.

Taylor’s first red carpet appearances were filled with Nashville innocence. This photo, from her first time attending the Academy of Country Music Awards in May of 2006, is a perfect example of her style at the time.

The floral, flowy maxi dress — along with her cowboy boots and loose curls — perfectly exemplifies her arrival as a young artist at the time. While she wasn’t a winner that year, the following year she won the Top New Female Vocalist award at the ACMs.

In 2007, still very much at the beginning of her career, Taylor proved that she wasn’t just a talented singer and songwriter. Her skills also extended to creating captivating music videos. That year, at the CMT Music Awards, she won the Breakthrough Video of the Year award.

Clearly, even back then, she knew she would become a musical queen as she wore a regal sea-green gown that looked absolutely stunning with her gold ringlets.

For the 2010 ACM Awards, Taylor went all out with a beautiful gown from Marchesa. She paired it with perfect Christian Louboutin heels. Now, being that she won four awards that year, we think it’s safe to say that lilac is Tay’s color!

But, the true stars of this look (besides the music star wearing it) were her diamond accessories from Neil Lane — which included a pair of diamond earrings, a diamond ring, and a sparkly diamond bracelet.

Although she wouldn’t commit to the bob fully until her 1989 era in 2014, it seems like Taylor Swift did try out the look several times over the years. This faux-bob perfectly complemented her golden Zuhair Murad dress.

She completed the glam and chic look — which she wore to the 2011 Vanity Fair Oscars Party — with a similarly sparkly Jimmy Choo clutch and some gold, peep-toe heels. This was certainly the beginning of an edgier Taylor Swift.

As well as romantic red carpet dresses and fierce on-stage looks, Taylor Swift is well known for her street style. This picture was taken during the Red era, after the singer released her fourth studio album. During this time, Swift was living in New York City and working on her next project.

The singer was regularly snapped leaving her building in adorable preppy outfits. Swift’s style choices from this period include lots of ditzy patterns, kitten heel pumps, and satchels.

Taking a step away from her usual red carpet looks, Taylor Swift appeared on the 2012 MTV Video Music Awards red carpet in a striking white suit. A fan of red lipstick, Swift debuted her now-classic look in this era. References to red lips are peppered throughout her music.

With the Red album, Swift veered into heartland rock and dance-pop, including songs like “I Knew You Were Trouble.” During performances, the singer often wore high-waisted shorts, a red striped top, and a ponytail.

2012 was a very good year for Taylor Swift. Her international success took center stage in Frankfurt, Germany at the MTV EMA awards. She gave an incredible performance of her song “We Are Never Ever Getting Back Together”.

Plus, she flew home with three impressive awards for Best Female, Best Live, and Best Look — which were voted for by audiences all around the world rather than a panel of judges. She definitely stood out with her many awards and her beautiful J. Mendel geometric gown.

Being invited to the Met Gala is how you know you’ve made it big as a star. But, it’s not enough to just go. You have to know how to fit the theme and rock an awesome outfit, too!

Taylor certainly proved over the years that, unlike some celebs, she knows how to perfectly fit a theme. We especially love the “Punk” J. Mendel gown she wore to the 2013 Met Gala, which perfectly matched the rock sounds of Red.

At the age of 24, Taylor Swift set out on an international tour after her album Red became a massive success. Like its namesake, the show featured Taylor in various red outfits.

This gown was worn on her show in London at the time. As part of the show, she also wore a shirt with a bedazzled Union Jack (the flag of England), as she performed alongside her good friend Ed Sheeran.

Between Red and 1989, Taylor’s edgier looks also made their way off the red carpet and into her day-to-day life. She transitioned from sweet dresses and funky patterns, to classier and more mature styles.

This picture of the singer was caught in early 2014 while she stayed in Los Angeles. While still preppy, the pressed button-up and plaited black skirt was definitely bolder than the romantic dresses of her late teens.

Red came with a song that has been a fan favorite for years. “All Too Well” has long been believed to be about her famous ex, Jake Gyllenhaal. So, it’s no surprise that before playing it live during the 2014 Grammy Awards, Taylor dressed for battle.

Her silver Gucci dress, which looks like a glam version of chainmail, was reportedly really heavy. Taylor described it as armor. This was certainly an impressive and intimidating look.

Here we have another picture of a casual Taylor Swift on the streets of New York City. In this case, the star stepped with a plaid duffel coat, a woolen beanie, and a gorgeous vintage-looking purse. During this time, Swift was working on her fifth album, 1989.

For the synth-pop-inspired record, Swift worked with a group of producers, including Jack Antonoff. This would prove to be a successful collaboration, as the pair continue to work together. 1989 was marketed as Swift’s first official pop album.

During the 1989 era, a 24-year-old Taylor Swift cut her hair into a shoulder-length bob. In this picture, the singer performs new single “Blank Space” at the 2014 American Music Awards. The song makes fun of Swift’s media persona, and in this performance, she fully embraced outlandish rumors about herself.

Other songs from this album include “Shake it Off,” “Bad Blood,” and “Wildest Dreams.” The accompanying tour was the highest-grossing tour of the year, making $250 million.

How incredible is this Taylor Swift look? Channeling 1950s fashion, the singer stepped out in this gorgeous vintage-inspired pastel look. This is another of the singer’s New York City street style outfits, and included a lemon houndstooth crop top and a pastel green fit and flare miniskirt.

This same year, Swift was named Billboard’s Woman of the Year. Around this time, Swift removed her catalog from Spotify and criticized Apple Music. In response, Apple changed their policy and Swift agreed to work with them.

For the 2015 MTV Video Music Awards, Taylor Swift wore a slightly different red carpet look. Rather than donning a dress or a slick suit, the singer-songwriter rocked a two-piece Ashish houndstooth set. Swift is certainly a fan of two-piece sets, and can be spotted wearing numerous coordinating outfits around this time.

The singer paired her Ashish outfit with slicked hair and smoky eyes. At the awards, Swift won Video of the Year for “Bad Blood” and presented an award to Kanye West.

For the premiere of 2014’s The Giver, Taylor Swift returned to her red-lipped, classic aesthetic. Wearing a Monique Lhuillier color-blocked gown, the singer looked like an old Hollywood star. The dress has a full, draped, pleated skirt, and a boat neck red top. Swift paired the gown with nude Casadei heels.

Considering that Swift wore this outfit shortly after donning her sequined Ashish two-piece, it’s clear that she’s a true fashion chameleon. For this look, the star was sure to add her customary red lipstick.

“Bad Blood” has been one of Taylor Swift’s biggest successes, with the music video being an instant hit thanks to the many celebs who joined her on it. So, it’s no wonder that after its debut, Taylor won big.

Showing up to the 2014 Billboard Music Awards in a foxy Balmain jumpsuit, Taylor returned home with eight awards! Those include the awards for Top Artist, Top Female Artist, Top Billboard 200 Artist and Album, and Tip Streaming Song for “Shake it Off”.

The 2016 CMAs were made extra special when Taylor Swift appeared on stage to give away the award for Entertainer of the Year (which she had won twice before) for the ceremony’s 50th anniversary.

Taylor absolutely shined in a Gatsby-reminiscent art deco Julien Macdonald dress. She certainly had come a long way since her 2009 win of that award for her Fearless album.

Following the success of 1989, Taylor Swift took home another armful of Grammy Awards. At the 2016 ceremony, at age 26, Swift won Best Pop Vocal Album, Best Music Video, and Album of the Year. Interestingly, this would be the last time she attended the awards.

As part of her acceptance speech, Swift encouraged girls and young women to take credit for their accomplishments. This was partly related to the ongoing feud between the singer and rapper Kanye West.

In 2016, before the release of sixth album Reputation, Taylor Swift stepped out in a bold look at the Met Gala. The singer was a co-chair for the fashion event and wore the bleach blonde bob that she had previously debuted on the cover of Vogue.

This bold look is a custom cut-out Louis Vuitton dress, worn with dark lipstick and lace-up shoes. This was the last time that Swift was seen in public for around a year.

The first single from Swift’s new album Reputation, “Look What You Made Me Do” topped charts in multiple countries. Other songs from the album include “Delicate” and “Getaway Car.” With her next tour, Swift would break her own previously held record for the highest-grossing US tour for a female artist.

For this tour, Swift’s costumes were designed by Jessica Jones. For her performance of “Don’t Blame Me” and “Long Live”/“New Year’s Day,” Swift wore this custom embellished gown.

With Reputation, Taylor Swift asserted her independence and artistry. Swift’s fashion choices around this time were edgier than her usual looks, and her music played with her celebrity persona. In the music video for “Look What You Made Me Do,” Swift dresses as herself from all of her previous eras, and stages amusing conversations between her prior selves.

For the 2018 American Music Awards, the singer wore this incredible holographic silver Balmain minidress with matching thigh-high boots. The musician shone like a disco ball.

Here’s another stunning street style shot of Taylor Swift in New York City. Moving away from the grungier vibe of Reputation, the singer stepped out in this bright pink NYC sweatshirt. While it might look like something a tourist would pick up in the city, this hoody is actually $895 from Balenciaga. Hey, she’s a superstar.

For this playful look, Swift wore Alexander Wang denim shorts, Guiseppe Zanotti boots, and a Christian Louboutin black backpack. Altogether, this outfit cost almost $4,ooo.

Following the success of the Reputation tour and album, Taylor Swift wasted no time in moving onto her next era. With Lover, all 18 of the album’s tracks charted simultaneously, setting yet another record for the musical powerhouse. Swift’s seventh album contained the singles, “The Man,” “You Need to Calm Down,” and “Me!”

The aesthetic for the Lover era was brightly colored and dreamy. In her live performances, the artist wore rainbow-colored looks complete with fringes and tie-dye.

Taylor Swift attended the 2019 Billboard Music Awards wearing a gorgeous lilac ruffled minidress. The gown is by Raisa and Vanessa, and almost nods back to Swift’s country roots. Taylor paired this dress with a studded ear cuff, an up-do, and natural makeup.

Lover ended up being 2019’s best-selling studio album, and Taylor Swift scooped up yet more awards for her songwriting, performing, and directing. Despite this, Swift was having issues with her label, which would only end up worsening.

2019 not only saw the release of her seventh album Lover, but it also had Taylor releasing one of her most successful collaborations alongside Panic! at the Disco singer, Brendon Urie. The music video for the song features both artists decked out in pastels.

The album, like the single, was deemed a triumph and whimsical. That’s also a great way to describe Taylor’s fashion at the time as she shined in light and fun pinks and pastels.

Taylor is clearly no stranger to winning big at award ceremonies. In fact, at the 2019 American Music Awards (AMAs), she walked away not only with five awards (including Artist of the Year) but also with the record of the most AMA wins.

She beat out Michael Jackson’s previous record. The late pop icon held a whopping record of 24 wins. But, with the AMA awards she received that year, she now stood at 28 wins!

At those same AMAs, Taylor performed in one of the most unique and iconic outfits, not because of its style exactly (although that too is as flawless as always). Instead, this look has been seen as an act of defiance.

The white jacket, adorned only with the name of her past albums has been seen as a protest against Big Machine Records holding the rights to the singer’s many songs. She also performed her song, “The Man” in this look.

Swifties know that Taylor Swift is a cat person. The artist has three cats named Meredith Grey (after the Grey’s Anatomy character), Olivia Benson (after the Scandal character), and Benjamin Button (after the Brad Pitt character).

As a result, the singer was thrilled to land a part in the 2019 film adaptation of the musical, Cats. Swift played Bombalurina, sang “Macavity,” and contributed an original song, “Beautiful Ghosts.” For the premiere, the star wore this floral, floor-length Oscar de la Renta gown.

For the 2019 Time 100 gala, Taylor Swift returned to her princess-style “Love Story” roots. Wearing a stunning custom J. Mendel dress, the singer was pretty as a picture in pastels. The singer wore her hair in a tousled updo and kept jewelry to a minimum.

Most excitingly, the gown’s sleeves are detachable, so Swift removed them for her performance. As many fans do, Swifties started speculating about whether this floaty look was in reference to an upcoming album.

At the beginning of 2020, Taylor Swift appeared on the front cover of Vanity Fair. In the accompanying interview, the artist commented on her ongoing issues with her music label. All of Taylor Swift’s back catalog is owned by her recording label, leading her to rerecord all of her albums so that she owns her property.

For this photoshoot, Swift wore her iconic red lipstick and a range of ski wear. According to the article, the singer no longer wished to be “polite at all costs.”

Another subject of the Vanity Fair article was Swift’s upcoming Netflix documentary, Miss Americana. For the premiere of the movie, Swift wore this gorgeous plaid suit to the Sundance Film Festival in 2020.

The houndstooth suit is by Carmen March, and Tay wore it with a belt, trench, and even matching shoes. The doc was directed by Lana Wilson, and followed several years in Swift’s life — from the Reputation tour to the release of Lover.

In 2020, Taylor Swift delighted fans with two surprise albums in quick successions. Folklore and Evermore were released five months apart and described as sister albums. They are both indie-folk records, making another stylistic departure from Swift’s earlier work.

For her performance at the 2020 Academy of Country Music Awards, Taylor Swift had to do her own hair and makeup. She opted for a Stella McCartney ensemble, including a sequined turtleneck, khaki pants, and black heels with gold chain ankle straps.

Taylor’s international success is well-documented, but it’s still truly amazing to see how beloved she is all around the world. Not only that but she’s been honored internationally, too! In May of 2021, she received the Global Icon Award at the BRITs.

With the award she made history! Not only is she the first non-British artist to receive the award in the show’s history, but she’s also the very first woman to be given this impressive award!

As the names of her two indie-folk albums suggest, Taylor’s outfits during her folklore / Evermore era were just that — folksy, floral, and flowy. 2021 also saw the singer take to the stage of the Grammy awards.

During the ceremony, she changed to a different flowy dress and performed a set including the songs “August” and “Willow” from atop a woodsy set. She also took home another Grammy for Album of the Year — her 11th!

Besides her two new albums, Taylor also managed to find the time in 2021 to re-record her previous album and release Red Taylor’s Version. The album also came with the 10-minute version of “All Too Well” alongside a short film.

Taylor adorned her own All Too Well premiere in a classy and suave dark purple velvet suit (alongside bright red nail polish). Taylor not only wrote the music but also wrote, directed, and acted in the short film.

Thanks to the singer releasing many of her “Taylor’s Version” albums in recent years, fans of Taylor Swift who tuned in to watch the 2022 VMA were hoping to hear when Reputation would be getting the same treatment. Instead, fans got a massive shock.

The award-winning artist instead shared at the awards that she was about to release a brand new album at midnight. This turned out to be her newest album, Midnight — which became an instant hit!

The last few years have been the most prolific in Taylor Swift’s impressive career. Not only did she release five albums in three years (three with brand new music), but she’s also released more new signals than the entirety of her career.

So, it’s no wonder she won the Artist of the Year award at the 2022 AMAs (alongside several other awards). She shined as bright as her many awards with a sparkly ‘70s-inspired jumpsuit by the Blonds. It seems her Midnight era is all about disco!

Taylor really has been into the disco glitter look in recent years, and it definitely works for her. Surrounding the hype of All Too Well: The Short Movie, the artist has been making the rounds at film festivals.

She wore this impressive piece by Lous Vuitton to the premiere of her short film/music video at the 47th Toronto International Film Festival (TIFF). Fashion icon that she is, Taylor also matched her sandals, jewelry, and nail polish to the beautiful gown.

In total, Taylor Swift has over 10 Grammy Awards, an Emmy, 27 Guinness World Records, 32 American Music Awards, and 23 Billboard music awards. The lead singles from her recent albums, “Cardigan,” and “Willow” each topped the charts, and Swift released a self-directed concert movie, Folklore: The Long Pond Studio Sessions.

Taylor Swift has now rerecorded and released her second album Fearless, and continues to do so with her other work. Always keeping it fashion fresh, the singer wore this Monse deconstructed short suit to the 2020 NME awards.