20+ Photos of World Famous Taylor Swift Throughout Her Career

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. Check out these pictures of the star throughout her celebrated career.

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.

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.

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.