As the youngest songwriter ever hired by Sony/ATV Tree Publishing, 14-year-old Taylor Swift arrived on the scene looking fresh-faced and innocent. She wore little makeup and kept her hair natural in tight curls. And you remember those poufy floral dresses, don't you?

Taylor Swift's 2006 Style At the beginning of her career, Taylor Swift wore flowy dresses and her natural curls, exuding youth and innocence.

The following year, Swift left Sony/ATV because she wanted to write and record her own songs. This bold step was also reflected in her style. She moved away from girlie prints and started to veer toward more sophisticated dresses. She didn't touch her natural curls — and she still had a distinctive air of youth — but there was progress.

With the release of a hot new single, Swift embraced her country roots with bright colors, big patterns and natural looking makeup.

Taylor Swift's 2008 Style After being dumped by Nick Jonas, Taylor Swift began embracing a sexier style, wearing sparkly mini dresses that showed off her killer legs.

Her 18th year was a big one for Swift. After dating for a few months, Nick Jonas broke up with Swift during a 27-second phone call, which inspired her first highly publicized breakup song, a genre she has since become known for. During this time, Swift was also nominated for a Grammy and released her second studio album, Fearless. She started to grow up in more ways than one. Her attitude toward men and her clothes changed. Her dresses were more body-conscious and sophisticated. Yet she always looked age-appropriate.

Taylor Swift's 2009 Style Taylor Swift wore a slinky and sparkly dress to the MTV Video Music Awards in 2009, when Kanye West infamously ditched her on stage while accepting her award.

Swift started to develop a reputation for kissing and writing — about breakups, that is. Some critics disliked the fact that she aired her dirty laundry in her songs. But Swift continued to soar in her musical career. Her singles topped the charts.

During that same year, Swift scored her first film role and became the first country artist to win an MTV Video Music Award. When accepting her award, Kanye West rushed to the stage, saying that Beyoncé should have won. This impulsive and insensitive move by West catapulted Swift into the spotlight.

Fans were unequivocally on her side this time. And Swift started to gain more confidence. She felt comfortable enough to experiment with straight hair, lower necklines and lots of sequins. She wanted to get noticed. And her clothes were doing the trick.

Taylor Swift's 2010 Style By 2010 Taylor Swift began experimenting with a bold red lip, and trying out chic hairstyles that looked more mature.

In 2010, Swift dated a series of high-profile men, including John Mayer, Cory Moneith and Jake Gyllenhaal. She also won four Grammys!

During the ceremony, she performed with Stevie Nicks. Surprisingly, the performance garnered negative reviews and an unexpected backlash. Her "Speak Now" album was released with enormous success and became one of only 16 albums to sell more than a million copies in the first week.

Swift was now a huge success. And her clothes on the carpet reflected that. She started wearing fire-engine red lipstick, sleek, pulled-back hair, and second-skin dresses. There was no young wallflower here!

Taylor Swift's 2011 Style Taylor Swift's red lips became a signature staple for the singer by 2011, and she opted for more sexy ensembles like this super-short mini dress paired with gold stilettos.

After a world tour, Swift's song "Mean" won Best Country Song and Best Country Solo Performance at the Grammy Awards. Older and more mature, scarlet lips and sexier silhouettes became the norm, not the exception.  But there was still a dichotomy between the sweet, young girl and the sex symbol. She had bits of each, and they were both coming through loud and clear.

Taylor Swift's 2012 Style While dating Conner Kennedy, Taylor Swift began wearing more retro-inspired outfits, both on the street and the red carpet, possibly in a bid to win over the famous family.

Swift began dating Conor Kennedy. Suddenly, she was photographed in more conservative, almost retro dresses and makeup. Some wondered if she was trying to fit in with the Kennedys. Many speculated that she was veering from her own style in order to win over potential in-laws. Did she give up parts of herself to fit in with the iconic family?

But the fairytale romance soon came to an end and Swift moved on to Harry Styles, the much-loved boy-band hottie from One Direction. Once again, Swift was almost five years older than the 1D star. Her hair, makeup and clothes varied widely during this time. Fans felt she was trying to mold her look to her new man. But the quick changes didn't do the trick, and soon Swift was single again.

Taylor Swift's 2013 Style In 2013 Taylor Swift went back to her roots, frequently choosing white dresses that looked less innocent in chic styles.

After much media scrutiny about her high-profile romantic relationships and breakups, Swift is single again. But we're sure this country crooner won't be single for long.

Dr. Jenn Berman is a licensed therapist in private practice in Beverly Hills. She is the host of VH1 Couples Therapy and The Love and Sex Show with Dr. Jenn on Cosmo Radio on Sirius XM. She is the author of two best-selling parenting books and one children's book. Dr. Berman is the creator of the No More Diets app, which is available for the iPhone and iPad. She also has an eco-friendly clothing line called Retail Therapy.