25 Pics Of Taylor Swift's Style Evolution (As Seen Through Her Romances)

Taylor Swift is an icon of the music world, a genre-bending musician, and media mogul. She was the first young superstar (who really and truly is a superstar) to gain worldwide popularity with a country music. However, over the last few years, she’s drifted towards pop-focused music, though any good musician will admit that their style and sound naturally shifts as the years go on. They discover new aspects of themselves and want to translate that through music. Sometimes, however, the new discoveries don’t quite harmonize with the old notes. That’s when the change happens, as we saw in Taylor Swift’s case.

Relationships are also a big part of what inspires affect singer/songwriters. As artists who tend to write about their feelings a lot, it only makes sense these artists would be affected by a new beau and the subsequent break-up. It wasn’t just Taylor Swift’s music that was affected by her fleeting relationships. Her style has shifted dramatically throughout her many moments in the sun with various gentlemen callers.

Below we'll break down Taylor Swift’s stylish looks, following the trajectory of her many romances, and we'll figure out if style-wise, she’s actually better off now than she was.

25 Her Girl-Next-Door Style Was Strong During Joe Jonas


Our teenage hearts were all aflutter when we read this news. Billboard reminds us that this Jonas drama happened all the way back in 2008, and while the feelings were fresh at the time they seem to have worked past it now. 2008 was when her style was still very girl-next-door. The blonde curls and the side bangs were quintessential late 2000s T-Swizzle, and were a perfect complement to Joe Jonas’s side part. Was this her ultimate fashion form? We don’t believe so, but it’s certainly a strong place to start.

24 Lucas Till Was A Brief Flash, But Also Featured Soft Styles


This one month of magic was a definite non-issue for Taylor Swift, as Billboard reports. Apparently, this guy, who was the romantic co-lead of her "You Belong With Me" music video, hasn’t even had a song written about him. While they only dated for the amount of time that filming the music took, she seemed to really embrace that sweet, country style of hers while she was with him. We didn’t even know that this was a relationship at the time it happened, which probably means there wasn’t much impact on Taylor either.

23 ...Not To Mention T-Swift's Other Choice 2008 Trends


Can we even talk about these trends without getting a little giggly? It’s awfully difficult, especially when it reminds us so strongly of our own past fashion faux-pas. As we can see here, Taylor Swift was always on top of the current trends. If only those trends back in 2008 suited people better! The fringed suede boots, the gray-washed jeans, the almost-cropped zip-up sweater, that drapey shirt it was paired with in quintessential 2000s turquoise… This is all of our middle school outfits merged into one bold look.

22 John Mayer Marked An Improvement In Her Fashion-Forward Options

bustle.com (Photo by Bryan Bedder/Getty Images)

Luckily John Mayer came along, which we mark as a turning point in T-Swift’s style. Telegraph reports that there was some controversy surrounding the two musical artists’ relationship, as their differences were made pretty public. They seemed happy for the 4 or 5 months they were together, despite the fact that it ended quickly. This is where Taylor Swift started to turn her outfits around. Maybe it was the “older man” or maybe it was the fact that we all realized the late 2008s were not a fashion era we should ever relive. Whatever the reason, her dresses became more grown up and her hair started to get that familiar wind-swept shape.

21 ...But She Still Rocked Those Sweet Boot And Dress Combos


She continued rocking a more grown-up style throughout the next year, transitioning to a minimal elegant silhouette. Her music style at the 2009 mark was still pretty saturated with country influence. While she’s decidedly pop-country, there’s a twang in her voice that pairs perfectly with these high-fashion cowboy boots. Did we really just say that? “High-fashion cowboy boots”? Well, when they’re on Taylor Swift, they just might count as a quality statement piece.

20 Jake Gyllenhaal Was A Surprising Stop, But Swift Certainly Started Rocking Her Look


They definitely deserved the “cutest couple” award, as Swift and Gyllenhaal were seriously adorable together. We would love to date Jake Gyllenhaal, as would most of the world’s population. With a little bit of blank space between her time with Mayer and Gyllenhaal’s introduction, she had time to work on that style. Telegraph says that this was only a three month relationship, but we saw even more growth of her style. She’s still rocking those straight-leg dark wash jeans because they're obviously classic.

19 Taylor Lautner Was A Time For Hats


Remember this cutie? Taylor Lautner was the first Taylor Swift relationship we really and truly followed. Maybe that’s because we always felt we should be dating him. Who doesn’t want a piece of Jacob the werewolf, right? Telegraph reports that this was another short-lived relationship, which sparked after the two met on the set of a movie. This was one of those fall-to-winter flings, which meant we saw her rocking a whole lot of flannel and hats. She also rocked that beautiful smile quite a lot, which might have been the only reason she pulled the styles off.

18 And Also For Getting A Little More Grown Up


Hats and jackets aside, she really did start to look a little more grown-up in this timeframe. While the John Mayer era saw her dressing up a little more, this was the rise of her casual clothing getting more grown-up. Graphic shirts, skinny jeans, and heels began to be seen on the singer/songwriter. She’s also starting to play around with other hairstyles, which we totally see as foreshadowing to her current styles. She didn’t know this at the time, but the low bun was eventually going to become a go-to style.

17 Cory Monteith Might Have Been Brief, But Big Changes Took Place


2010 was definitely another shift. Swift’s career is bubbling, and she’s starting to be seen more and more publicly as a powerful woman. Billboard tells us that this relationship with Monteith lasted but a single month. However, it sounds like there was at least one song that he inspired, solidifying him as a tried-and-true T-Swift boyfriend. While the one month likely had a negligible impact on her style as a whole, we are seeing some development here. She’s starting to embrace a more polished look and is shedding her girl-next-door style.

16 Just Look At This Hair!


See? Sleek and stylish! This is one of the first times we started to see Swift embrace a straighter hairstyle, which elevated her from sweetie to suave. The chic look that we know and love on Taylor Swift is certainly not present in her previous outfits. Today’s Taylor Swift seems to embrace a lot of classic lines, mono-colors, and clean looks. This hair is the beginning of her chic era. There’s still a long way to go, though. Let’s look at her forays into this world of elegant adult style.

15 Eddie Redmayne Brought Us Into T-Swift's 2012


This adorable guy is everyone’s favorite fantastic beasts catcher. He was also on the hook for dating Taylor Swift back in 2011, though Billboard says that he spent a while denying the relationship. To be fair, Swift didn’t seem inspired enough to write a song for him. The seeds of her grown-up style have sprouted, but have resulted in a color palette we seldom see her in now. The lines are the same, though: A-line skirt, a well-fitted sweater, and heels.

14 And She Brought In The Bangs-And-Bold-Lips Look


This is the Taylor Swift we all know! Red lips, slick hair, and a white and black outfit that’s totally classic. Even her song Wildest Dreams referenced the fact that she wants to be remembered in nice clothes and red lips. Okay, we’re paraphrasing a bit there. But it’s still true that she and the three most classic colors definitely fell in love in 2011. Red, white, and black, just pop against her blonde hair, and make her look so put-together.

13 There Was A Brief Fling With Efron...


Zac Efron was the most famous relationship of Swift’s that was never actually a relationship. Not only did they deny dating rumors left, right, and center, but Billboard reports that they even wrote a parody song together whose message was very clear: they’re not dating! That being said, the rumors were enough for us to include him in the article. After all, who could ignore this white dress? It’s a great attempt from Swift to explore more experimental red carpet looks, but we’re kind of glad this dress was never seen again. It made space for much better styles!

12 ...But We Paid More Attention To Her Suddenly Amazing Looks


See? Efron was a flash in the plan, but Swift’s style was growing every day. This gorgeously patterned dress might be a little out of the norm for her current style, but back then it was the cream of the crop, fashion-wise. The duster jacket is still popular, proving that Swift might have even been ahead of the curve. The color palette is questionable, but for a spring/summer look we actually think it’s kind of cute. The guitar is a quintessential Swift accessory that warmed our hearts to see coming back too!

11 Next Was When She Matched Her Red Album


Red is a relationship unto itself. She skyrocketed with this album, at least in our minds. Her fashion choices around this time were more linked to her album rather than her current partner, which was a very smart move for all those red carpet interviews. For an album that seemed more like a tell-all about her relationships than about anything else, we think that the Red era deserves a spot alongside all the boyfriends it was about. Taylor Swift is a powerhouse, and Red proved that for us.

10 Swift's Girl-Next-Door Style Really Solidified In That Era Too


Once the media fervor for Red diminished (though let’s be real, it’s still one of our top-played albums on Spotify) Taylor Swift went back to her old style ways. This time around, however, she seemed to embrace her girl-next-door looks a little more. 2012 was a time of change for most of us, including stars like Swift. She started appearing more and more in sweet dresses and sensible shoes but kept that red lipstick perfectly placed. Maybe that’s why she ended up in the arms of…

9 The Hottest Couple Award Went To Her And Harry Styles (Thanks In Part To Her Fashion Choices)


That’s right. Harry Styles. Styles and Swift were so adorable together and were the pinnacle couple of 2012-2013 pop. With him in One Direction and her running quickly towards superstardom, this was a power couple that truly stole our hearts. Apparently, this short relationship had a rough ending, which was all the fuel Swift needed for her later album, 1989. That’s some hot gossip, just like her fashion choices at this time. And we’re not just talking about her winter wear, which was almost exclusively what we saw these two in.

8 And Then It Was Back To Classic Black And White Looks


Taylor came out the other side of that relationship refreshed and relaxed. She’s really rocking those red accents against her black and white base. This is the Taylor Swift many of us know as adults. She’s a rocked a similar style for a few years now, and we think that the next couple relationships have really solidified this as her signature style. It’s almost impossible not to imagine Taylor Swift in one of those three colors. We can’t help but picture what she looks like in the next photo...

7 She REALLY Embraced That Classic Chic Style


This is the classic look that we fully expect from Taylor Swift nowadays. While we sometimes see her in some fun and flirty styles, the haircut and the classic clothes are truly defining features of Taylor Swift. This is the outfit that defines her style for sure. Tight leggings, a powerful faux blazer, perfectly blown-out hair, and those luscious red lips. No matter how hard we try we just can’t emulate this style. It’s so Swift, and she’s going to rock it for a long time.

6 And Her Most Prolific Relationship (Calvin Harris) Also Caused A Big Change


Just because she’s so super powerful doesn’t mean that she has to dress like it all the time. We all remember the situation that was the ending of Taylor Swift and Calvin Harris’ relationship. Telegraph mentions how they were together for a little over a year before things ended between the two of them. Throughout her time with Harris, she seemed to unlock her fun side, featuring overalls, crop tops, and a more youthful approach to style. She integrated these into her classic-chic color palette, as well as her other grown-up clothing items.

5 She Cut Her Hair!

time.com (Photo by James Devaney/GC Images)

That “fun” side was definitely full of some bold choices. Not only did she seem happier when she was with Calvin Harris, but she also ended up making a drastic decision that changed the course of Taylor Swift style history: she cut her hair! Her short hair became the stuff dreams are made of, flirty and fully curled the many times we saw it. She added more diversity to her style by throwing in some colorful combos but kept them in her realm of well-polished style by ensuring that they were always matching.

4 Tom Hiddleston Was When She Brought Out That Practical Fashion


Just two years ago Swift and Hiddleston were seen on social media snuggling and snorkeling, travelling and trailblazing in their chosen career paths. Telegraph, however, reminds us that this only lasted about 3 months. The two of them were surprisingly not as serious as some of Swift’s other relationships, making us unsure if she’ll ever write any songs about him. Her style seemed to slip back into old habits here, though she still had a few fun and young pieces mixed in her wardrobe.

3 But Swiftly Ditched It After, Instead Rocking A More Daring Design


After those three months, Taylor Swift’s style became a little more daring. She’s managed to find her edge, which is a style we’ve never actually seen on her before these last couple of years. She styled her bleached platinum hair with a light tousle, and when paired with her shiny leather jackets and favorite colors (red, white, and black), it’s a powerful and saucy look. It seems like a natural evolution. There’s no going back from that Look What You Made Me Do music video!

2 Her Most Recent Styles Have Been Giving Us Life


It’s not all edge for Taylor Swift, keep in mind. She’s still that sweet girl who got her start in the pop-country realm, pulling off the girl-next-door look perfectly. Now, however, it’s more of a… Young-woman-who-owns-the-penthouse look. She’s indisputably looking more and more adult, with a gorgeous style that’s a combination of creative, classic, and cute. That boldly striped bodysuit is giving us life, and her short hair makes her look even leaner and taller than she already is. 

1 Could It Be Thanks In Part To Her New Boy?


We don’t want to assume, but we think Joe Alwyn has been a great guy to Taylor Swift. Sure, he lives at home (according to Telegraph) but many of us do that in order to truly pursue our art. This is the most low-key relationship Swift has had, which makes us curious about what’s going on. Telegraph speculates that they’ve been together since 2017, potentially putting them almost at the year mark, if not more. Her style has been on point lately, so whatever they’re doing… Keep doing it.


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