Taylor Swift's Best Short Hair Moments

When it comes to how Taylor Swift presents herself to the world, she tends to play it safe. Unlike other celebrities, most notably Zendaya and Florence Pugh, the latter of whom went so far as to shave her head for a role, Swift seems to prescribe to the idea that not rocking the boat, especially when it comes to fashion and style, is best. This also might explain why Swift continues to miss the mark when it comes to her outfit choices, despite all her fame, money, and access to the world's top designers.

So when Swift cut the long natural curls for which she'd become known, it was fairly shocking. "I actually cut my hair here [in London], in the O2 arena backstage," Swift told Kiss FMUK in 2015, per People. "All my friends watched, including Ellie Goulding. I was planning it for six months. I was like, I'm doing it. I'm cutting my hair. I'm changing my hair for the first time ever." Granted, Swift had played with bold hairstyles in the past, but in many of those cases, those were wigs. Because a wig can be just as quickly taken off as it can be put on, it's not exactly a daring approach.

While Swift's short hair era was fairly short-lived, she appeared to have fun with it and there were a lot of great looks because of that. If you're a Swiftie who's thinking of cutting your hair, let Taylor be your inspiration.

In 2016, Taylor Swift attended the "Manus X Machina: Fashion In An Age of Technology" Met Gala rocking a short, shaggy platinum 'do. As co-chair for the Met Gala that year, Swift went above and beyond sticking to the theme of the night in her custom Louis Vuitton dress — mostly because Anna Wintour was behind the scenes, pulling the strings.

"We thought that we could take Taylor — who is a beautiful, beautiful girl but has been a little bit more conservative in her fashion choices and turn her into a Hedi Slimane rock n' roll girl," Wintour said of Swift on Vogue's podcast, per Haute Living, shortly before the gala. "What was so great was that she was completely up for it and loved it, and is going to hopefully continue with this look." As we know now, Swift didn't continue the look for very long.

Taylor Swift attended the 2015 iHeart Radio Music Awards, with a wavy, mousy blonde lob. Also known as a long bob, the lob is the perfect gateway to short hair. Or in Swift's case, it's a baby step toward going much shorter and much blonder, and all at the behest of Anna Wintour for the following year's Met Gala.

Although Taylor Swift has a gorgeous natural curl pattern in her hair, when she committed to the iconic, classic bob — the one that Anna Wintour has had since she was 15 — it was a fantastic choice. While anyone can cut their hair into a bob, it doesn't mean that everyone is going to pull it off and look amazing in the process. However, Swift was able to do just that, so when she showed up at the 58^th Grammy Awards in February 2016 with this cut, jaws dropped in the best way possible.

The thing with cutting your hair short is that you then need to grow it back out — or just keep it short forever to avoid those in-between awkward stages. But when Taylor Swift was spotted in September 2016 in Tribeca, just a few months after that year's Met Gala, it was clear that she was flawlessly navigating the growing out process. Swift was blonder than she usually is, probably due to the brief platinum era, and her side-swept bangs with the shoulder-length bob complemented each other perfectly, in a low-key, casual way.

In 2014, Taylor Swift took to the stage at the 2014 iHeartRadio Music Festival in Las Vegas. At this point she had a lob, but with some heavy French bob vibes thanks to her natural curls and bangs. It was a fun and playful look that, like all haircuts that linger just above the shoulders, was destined to get shorter — which it did in the two years that followed.