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Fearless and Fancy-Free
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.
A Purple Princess Dress
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.
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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.
Grabbing Those Grammys
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.
Debuting Straight Locks and Bangs
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.
The Speak Now Dress
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.
Preppy and Perky Street Style
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.
Striking in a Suit
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.
Plaid Coats and Beanie Hats
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.
Bobs and Blank Space
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.
Channeling Fifties Fashion
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.
Sparkly Sets and Slicked Hair
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.
Pleats to a Premiere
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.
Color-Blocked Coolness
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.
Bleach Blonde at the Met
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.
Custom Looks on Tour
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.
Stunning in Silver Balmain
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.
Stunning Street Style
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.
The Colors of the Rainbow
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.
Looking Regal in Ruffles
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.
Looking Classy for Cats
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.
Perfect in Pastels
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.
Always a Cover Girl
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.”
Taylor Swift: Miss Americana
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.
Doing it Herself
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.
She’s Still Changing it Up
In total, Taylor Swift has 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.
