Taylor Swift's Gorgeous Style Transformation
Taylor Swift is many things. She's a multi-award-winning artist, a doting cat mom, a singer, songwriter, daughter, sister — and, of course, one of the entertainment industry's biggest style icons. But with great responsibility comes great power, and Swift has millions of followers in the palm of her hand. Over the years, we've seen Swift transform from a sweet high school girl singing songs about Tim McGraw in cowboy boots to a strong, independent billionaire selling out arenas across the globe. And whatever she's wearing, fans have to have it.
From her staple red lipstick to the sequins synonymous with her "1989" era, Swift has shown us time and time again that she knows how to build an aesthetic. Her fabulous on-stage outfits are one thing, but her casual style is equally impressive — but was it always so?
Just like any famous icon, it took Swift a little while to find her groove with fashion. As her music evolved, so did her look, making the leap from sweeter-than-peach-tea country starlet to bona fide pop princess.
Taylor Swift's 2006 CMT look was plain and simple
It's hard to believe that Taylor Swift has been in the industry for almost two decades. In 2006, she was signed to Scott Borchetta's Big Machine record label, and the song "Tim McGraw" was born. The iconic hit was a country summer bop for the 16-year-old, which meant that she was well on her way to stardom. Because of her newfound success, Swift was invited to the CMT Music Awards that year, gifting us with this unforgettable look from her early days. Swift showed up to the ceremony in a relatively simple white dress with black detailing.
The dress was very age appropriate and classy, but it was Swift's long curls that really stole the show. Her golden blonde tresses were a signature trademark for her back then, cascading down her shoulders and framing her fuller cheeks. Swift's makeup is noticeably minimal when compared to her later style, with no red lipstick in sight. Instead, the singer kept it simple with mascara and a nude shiny lip.
It's giving country girl who is ready to take on Nashville — and, at the time, that's exactly what Swift was gearing up to do.
She rocked cowboy boots and a scarf dress
In May 2006, just a month after attending the CMT Music Awards, Taylor Swift appeared at the 41st Annual Academy of Country Music Awards. Though she was still a new face on the scene at the time, Swift was able to rub shoulders with big names like Carrie Underwood, Dierks Bentley, Eric Church, and Kelly Clarkson. She was just a guest at this event — not a performer like she would be the following year – but she made sure she was dolled up for the occasion. And her outfit is just about as country as it gets.
The bright young teen wore a scarf dress with a floral pattern, pairing it with heeled brown leather cowboy boots and big, gold hoop earrings. It was the aughts, and fashion was a bit different (to say the least), so while it may not seem the most stylish choice now, it was pretty on-trend at the time. Swift seemed to be getting more comfortable on the carpet, going for a more colorful palette compared to her subdued black and white CMT Awards look.
Taylor's signature tight curls are long gone by 2009
Over the next couple of years, Taylor Swift's stunning transformation was well underway. She was busy performing at awards shows and becoming a much bigger name in the music scene, securing her spot as one to watch. Though country music fans may have been well aware of her, it wasn't until the drop of her 2008 album "Fearless," which features songs like "You Belong With Me" and "Love Story," that she transitioned into the mainstream pop world. By the time she appeared on MuchOnDemand Live in January 2009, she was a global sensation, and her style had begun to change considerably.
For this live interview, Swift wore a chic black dress with ruffle detailing and sheer striped tights. The outfit, which resembled something of a gothic Victorian doll, was much more sophisticated and put together than some of her previous looks — but it's her hair that really saw the most change during this time. Swift's super long, tight ringlets disappeared to make way for more refined, shaped, and styled curls. The color was also slightly more golden, indicating that Swift had taken a trip to the salon.
What's more, her cosmetic preferences were also elevated. Her eyebrows and eye makeup were darker, giving her a more grown-up look, while her lips appeared slightly plumper with a darker shade of pink. All in all, Swift appeared to be adopting a more controlled and cohesive look than previously — and it worked!
Taylor's red lipstick makes its arrival
One of Taylor Swift's most iconic looks is, without a doubt, her signature red lip. It's what ice is to tea, what cookies is to cream — we just can't imagine a world where Swift doesn't sport it. However, when she was a youngster making her way in the industry, Swift stuck to neutral tones. That began to change when she was convinced to try red lipstick at a 2009 photoshoot for Allure. As Gucci Westman, the makeup artist for Swift's shoot, told Elle, Swift's management initially refused the red lip but eventually relented It still took Swift a little while to start wearing the shade on the regular, but when she did, there was no stopping her.
In 2011, Swift wore a little black dress to a Covergirl event. The strapless number showed off her porcelain skin that was only accentuated by a bold lip and peachy blush. Her heavy eye makeup and cute updo created an old Hollywood vibe that the singer would lean into several times throughout this era. This same year, she won the CMA Entertainer of the Year award, proving she was still straddling the line between country starlet and pop artist.
Swift was still quite young, but her style was beginning to mature.
Her on-stage outfits get a makeover
If you were to take a deep dive into every one of Taylor Swift's eras, you would see just how much the singer has evolved. If you haven't guessed already, Swift has never shied away from change. Just like any young woman in the spotlight, Swift's style began to drastically alter as she made her way into her 20s. In 2012, she kickstarted her "Red" era, as she dropped the album that year. "Red" is a fan favorite for a number of reasons, not least because it contains smash hits like "I Knew You Were Trouble," "22" and "We Are Never Ever Getting Back Together."
The front cover of the album is a close-up of Swift's face and her prominent red lips, which wasn't entirely surprising considering her lipstick was a near-constant presence by this time. With that being said, these years were really important for Swift's style, especially on stage. To perform at the 2012 BBC Radio 1 Teen Awards in London, the hitmaker wore a sheer bejeweled black top tucked into high-waisted silver shorts. She also sported a fuller finger and darker blonde locks for the occasion, which gave her an edgier appearance.
If Swift's early style was a testament to her country girl start, then this was a reflection of where she was — goodbye Nashville, welcome to New York!
Taylor sports an edgy jumpsuit in 2014
Considering just how long she's been in the business, it's only natural that Taylor Swift's best — and worst outfits – aren't easily forgotten. Some of them are so iconic we'll never get over them, while the less said about others, the better. Even so, we have to respect the fact that Swift has always played with fashion. In 2014, she attended MTV's Video Music Awards wearing a seriously short jumpsuit. While Swift's endless legs looked phenomenal, fashion pundits weren't exactly sold, with HuffPost dubbing it "interesting" and " a bit ... different.' Make of that what you will!
By this point in her career, there was no stopping Swift. She was selling millions of records worldwide and was on top of her game, which might be why she opted for this power outfit. The romper, made by Mary Katrantzou, was paired with leather cut-out heels by Elie Saab and simple yet effective jewelry by Lorraine Schwartz and Ofira.
Perhaps Swift's most important accessory here is her attitude. Posing for photos with one hand on her hip and a bold stance, Swift can almost make us believe that this outfit was the right choice. Even if it's not a firm favorite, we have to appreciate just how far Swift's style had evolved by 2014.
1989 meant Taylor Swift's style went big
Diehard Swifties know that "1989" marked a much bigger transition into pop than the singer had ever done before. While the meaning behind "Wildest Dreams" might be pretty clear now, back then, we were singing our hearts out, wondering who it was about and wishing we looked half as cool as Swift in sequins. The album is named after Swift's birth year, and she milked the aesthetic to the core. In true '80s fashion, the Grammy winner blew out her bob and made sure her on-stage costumes were glittery and nostalgic.
While performing in Australia during her "1989" World Tour, Swift made sure her look was fun and to the point, pairing the crop top and skater skirt with a blue sequin bomber jacket and white Wayfarer sunglasses. Tom Cruise himself would have been envious! If there was ever any doubt that Swift was unsure of how to dress for the occasion, then this cleared it right up. By this point, she was a pro at switching it up.
Taylor's street style gets edgier and moodier in 2017
By mid-2017, Taylor had made a triumphant return with "Reputation", shedding her good-girl image once and for all. We all know that the infamous feud between Kanye West, Kim Kardashian, and Swift fueled this new era, prompting Swift to take some time out of the spotlight while she planned her next move. When she came back, her aesthetic was a lot darker than it had been previously, perhaps to match the content of her "Reputation" album, which included hits like "Bad Blood" and "Look What You Made Me Do."
For a "Saturday Night Live" afterparty in November of that year, Swift wore a black satin bomber jacket with combat boots, which was a big departure from her style just a few years earlier. Her on-stage outfits from this period were also void of bright colors, with the singer opting to stick to dark hues to suit the mood. Considering what was happening at the time, who could blame her?
Swift ditches black and does fairytale classic
Following up "Reputation" was always going to be difficult, but Taylor Swift made it look easy peasy. In 2019, Swift released her album "Lover," which couldn't have been further from "Reputation" aesthetically, as it paid homage to Taylor Swift's then-boyfriend Joe Alwyn and their relationship. Though it's over and done with now, Swift was head over heels for her London boy at the time, which was reflected in her playful style. She ditched the black and went for pastels, often appearing at events and performances wearing shades of purple and pink.
Her look for the Time 100 event in April of that year was ethereal. Swift wore a gorgeous pink and yellow gown, complete with puff sleeves and floral embroidering, paired with a subtle headband. She glowed like a fairy princess. While this choice was reminiscent of some of her earlier looks, it brought a modern twist. The easy, breezy, bright, colorful, and carefree style from this time suited the songs she was singing perfectly, proving that Swift's music doesn't have to be centered around failed relationships to be successful, but happy ones, too!
Taylor Swift's hairstyle shifted
For a time in the 2010s, Taylor Swift's hair didn't change that much. She maintained her blond waves and shaggy fringe, sometimes glamming it up with a cute updo for an event. By the time she released her "Folklore" and "Evermore" albums, though, she had changed it up again, opting for a messier, dirtier blond curly 'do with a wavy fringe. Swift also stripped back her makeup at this time, ditching her red lip and sticking to nude tones with minimal eye makeup. Once again, her style evolved to match the music she was releasing.
These albums presented a more natural, less poppy and more folky sound, which Swift matched with her aesthetic as 2020 progressed. For the 55th ACM Awards at the Grand Ole Opry, Swift wore a deep red sequined top with high-waisted beige chinos. Her laid-back look gave her the appearance of a mature country star who had nothing left to prove — which wasn't far from the truth.
Her chainmail dress turned heads
By 2022, Taylor Swift was a fully-fledged adult in her 30s. As she said goodbye to the "Folklore" and "Evermore" era, the singer-songwriter began to pull out all the stops for events, sporting a tan and a fuller fringe. For the MTV European Music Awards, the hitmaker wore a black dress with chain mail detailing, pulling off the risqué look with supreme confidence.
The peachy-fresh makeup look she wore just a couple of years prior was nowhere to be found. Instead, Swift wore heavy winged liner and a blunt fringe. Of course, as a style chameleon, this wasn't unexpected, though some fans may have preferred the "Lover" aesthetic.
Swift also won an award that night — no, not for best dressed — but for Best Artist. Was anyone surprised?
Taylor's NFL wife look is as chic as it gets
Taylor Swift's past relationships have always been headline-grabbing, but none more so than her romance with NFL star Travis Kelce. By the tail end of 2023, Taylor was a fixture at Travis Kelce's ball games following her split from longtime love Joe Alywn. Her off-duty style largely consisted of jeans and a simple top, with her hair pulled back, making for a more relaxed look — though the red lip was still in place.
At the Super Bowl, Swift could be seen wearing a black top and black jeans combo with subtle gold jewelry and slightly frazzled ponytail. Even though it's a pretty basic look, it went down a storm, proving that Swift can do off-duty style even better than the next pop star.
Though she kept her trademark red lip, there was something about this look that showed just how refined her casual aesthetic can really be — and just how far the star has come in recent years.
Swift's eras tour style is unmatched
No breakdown of this popstar's style would be complete without a look at "The Eras Tour" wardrobe. Taylor Swift has an intense workout plan for these non-stop shows to keep her in peak condition, and it's not hard to see why. The costume changes alone are enough to leave us breathless. Swift looked more confident and stronger than ever, sporting a more muscular frame and a series of bedazzled leotards coupled with custom-made Louboutin boots.
Though Swift's show sees her wear outfits from every era of hers over the years, it's the leotard that has gotten the most attention. The rhinestone number sparkles perfectly in the light and is the perfect reflection of what she's achieved over the course of her career, adding yet another iconic look to the list.
Fans the world over have scrambled to make their own version of it, with some painstakingly gluing sequins together for hours to pay homage to the best in the business — Taylor Swift.