The Beauty Evolution of Taylor Swift, from Curly-Haired Cutie to All-American Icon

It’s hard to pick Taylor Swift’s most enviable quality. She’s been winning Grammys since the days when most of her peers were in high school, has a knack for penning relatable lyrics, and always rolls up in the best company (with her squad, obv.). Then there’s her style, both on and off the red carpet, that always manages to look equal parts pulled-together and effortlessly cool. Oh, and she also bakes with Karlie Kloss and counts Lorde among her closest friends. No biggie.

Of course, we also have to give a shoutout to her beauty prowess, because she’s definitely come a long way from her “Teardrops on My Guitar” days. Let’s put it this way: When you trade your long, flowing hair for a chic ‘do that instantly earns you comparisons to the hottest supermodel du jour, you know you’re on-trend.

Although most of us equate Taylor with her most frequently worn signature look (her perfectly red pout and next-level hair), she’s switched it up on the red carpet more than you might think. Not one to go by the book, she’s made some non-standard beauty choices, like wearing blue on blue or extending her bangs far past the recommended eyebrow-grazing length. Basically, whether she’s pouring out her heart or trying out a new beauty look, she’s always (to quote a certain album title) fearless.

Click through the slideshow to witness her beauty evolution, and let us know what your favorite looks are in the comments below.

April 200616 year-old Taylor shows up on the CMT Awards red carpet with a fresh face, windswept curls, and a barely-there wash of light blue eyeshadow.November 2006

Half a year later, she’s essentially sporting the amped-up version of her previous look. Think glossier curls, darker lashes, and more defined eye makeup—with the same natural pink cheeks and pink lips.

May 2007At the ACM Awards, she swaps her golden ringlets for a wavy updo and plays up her eyeshadow, keeping it slightly smoky and defining the inner corners with a trace of flattering white shimmer.June 2009Here’s another noteworthy winged liner moment, this time paired with an elegant tucked-and-pinned updo.November 2010Taylor channels Barbie beauty in this red carpet transformation unveiled at the AMAs. Take note: sleek hair, blunt bangs, and fluttery faux lashes make for a head-turning triple threat.

February 2013Back to bangs! She hits two hair trends in one with the addition of a milkmaid braid. Fringe this long tends to overpower eyes, so draw them back out (as Taylor does) with intense black liner blended with navy eyeshadow.December 2014Taylor’s sleek, blunt-cut lob frames her graphic look at KIIS FM’s Jingle Ball 2014. Just an exaggerated winged eye is all it takes to add edge to an otherwise classic style.

July 2015Leave it to Taylor to take a floral embellished headband to the next level. She wears it like a fairytale flower crown and looks just like a princess as she walks the NYC streets. The feline flick only adds to the gorgeousness.February 2016For the better part of early 2016, Taylor showed off her more refined side. With a curled under bob and a classic orange-red lip (that perfectly matched her dress, mind you), Tay would have looked just as at home in a 1950s rom com as she did on the red carpet at the Grammys.

May 2016After debuting white blonde tresses at Coachella, Taylor’s style took a seriously edgy turn. Showing up to Gigi Hadid’s 21st birthday party in L.A. With a dark oxblood lip and minimal eye makeup, the superstar proved she still has a few surprises left in store.

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