13 Taylor Swift Looks Proving Our Girl Is A Boss

13 Taylor Swift Looks Proving Our Girl Is A Boss

Taylor Swift is an unfaltering icon in fashion. That being said, alongside her obvious 'fashion figure' status is the more important fact of what we refer to as “boss status.” That is, the moments that prove her to be an inspiration; an undeniable force in the music industry; a brilliant creative; a person who speaks out against toxicity and speaks up for those who need a voice; and, a woman who continually shows vulnerability in her music and strength in her actions. Here are 13 times Taylor showed us just what a boss she is, told through the lens of key looks in the last decade of her career.
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Taylor Swift is an unfaltering icon in fashion; her street-style or now rare red carpet appearance is a favorite topic for journalists. That being said, alongside her obvious 'fashion figure' status is the more important fact she has what we refer to as 'boss status.' That is, the moments that prove her to be an undeniable force in the music industry; a constant creative; a person who speaks out against toxicity and speaks up for those who need a voice; and, a woman who shows vulnerability in her music and strength in her actions. So here are 13 times Taylor showed us just what a boss she is, told through the lens of key looks in the last decade of her career.

1. Winning the Pandemic Grammy

Image credit: NME

Taylor has never disappointed when it comes to Grammy dresses. I mean, the origin story of this article is because her style moments are consistently rendered iconic. But this red carpet look takes the cake because of this dress’s obvious beauty, the obvious Album Of The Year win, and this dress's connection to the album that brought her to the red carpet that night. So what's so obvious?

Image Credit: The West Australian

Designed by Laura Kim and Fernando Garcia of Oscar de la Renta, it’s quite possibly the most romantic and ball-in-fabled-town style dress we’ve ever seen. Accessorizing with a matching three-dimensional mask adorned with hand-embroidered flowers, the design is a page ripped from a Victorian journal of pressed flora and totally at home in the lyrical pages of folklore

It paired well with the winner’s podium as Taylor accepted Album Of The Year. That win was for the aforementioned folklore, the surprise album that brought the world together during the height of COVID-19 lockdowns, uncertainty, fear, and unprecedented pause. Written and produced in a matter of months, Taylor stepped into the metaphorical woods and invited us along as she spun tales of vengeful dead wives, exiled lovers, and illicit love affairs. She sung from three perspectives of a teenage love triangle, connected the heartache and hardship of the pandemic ICU with the ghastly beaches at 1942's Guadalcanal Campaign, and altogether delivered the best lyrical examples of her career to date when we needed an escape the most. While most of us were understandably struggling to find the motivation to get off the couch, Taylor was recording a Grammy-winning album remotely from hers.  


2. The All Too Well Short Film

This past Friday night, fans flocked to the AMC Lincoln Square in Manhattan for the premiere of Taylor’s short film for her freshly-released track “All Too Well (Taylor’s Version)." The 10-minute opus is a post-mortem of her short-lived, heart-wrecking love affair occurring over a decade ago. Taylor consistently thanks her fans for resurrecting the song; it was never a single, yet it’s arguably her most beloved track. Taylor directed the film (which is littered with easter eggs, of course) and the fall aesthetic through the lens of 35mm film. 

Image credit: Teen Vogue

For the premiere, Taylor wore a purple velvet Etro suit with black satin lapels, gold buttons, and a double-breasted silhouette. Paired with Alexandre Birman stiletto boots and a pink lip - she certainly proves she is “The Man” (this pun will make sense later). 

And why, pray tell, was this song from a 2012 album re-released? Here’s a crash course on why Taylor is re-recording her masters:

Above image from All Too Well Short Film. Image credit: The Harvard Crimson

Like the majority of record deals, standard legal arrangements give the recording company ownership of the copyrights of musical recordings, also known as a 'masters'. Taylor signed with Universal Music Group in 2018 which gave her ownership over her masters going forward, but she doesn’t own her recordings prior to 2018 under Big Machine Records. Taylor claims she repeatedly tried to buy her masters, but it was instead allegedly sold without her knowledge to Scooter Braun’s Ithaca Holdings for a reported $300 million. 

So for someone like Taylor, who has paved her way as a woman in a male-dominated industry, broken her own records, faced sexism (read on for details), and continues to thrive under media scrutiny, owning her own work is naturally very important. She is re-recording her masters under her new label so she can own her own work. It’s a brilliant business move because she’s including never-before-heard tracks from her past album eras that didn’t make the cut initially. Why wouldn’t you exclusively listen to her re-recorded versions which include new songs instead of the versions Ithaca owns? More royalties into Taylor’s pocket is literally music to our ears.

3. Taylor X Stella McCartney Collab


As if one album wasn’t surprising enough, in December 2020 Taylor released another LP, just a mere five months after dropping folklore. As she puts it, her and her musical collaborators “just couldn’t stop writing songs.” Evermore is her 9th studio album and a storybook of wintery-witchy-wonderous examples of superior production, easter-egg-trails intertwining with earlier albums, and creatively-spun insight into the perspectives of other people - something Taylor is eerily good at. Two albums, one year; and that year was 2020? What a boss. For the album cover and artwork, she wears Stella McCartney. Quick story on that:

Image credit: New York Post
For Taylor’s 2019 album Lover, Stella and Taylor partnered for the Taylor X Stella merch collection, a lookbook of pastels based on tracks from the album. It’s not a surprise that Taylor, someone in tune with style trends, would break into the fashion industry. We wouldn’t be surprised if she dropped a Swift brand clothing line one of these days. Get us on a list for a folklorian summer dress stat!

Image credit: Vogue

4. From Silence to Sundance

In 2018 Taylor opened the American Music Awards during her reputation album era. Wearing a silver “disco ball” Balmain dress and matching thigh high boots, the ensemble came together with square Ofira jeweled earrings and Lorraine Schwartz rings. In the couple years leading up to the reputation era, Taylor was noticeably absent from red carpets following widespread media scrutiny over that infamous Kim-Kanye phone call that we won’t give power to by validating in text. Long story short, news outlets have done what they often do and that is paint Taylor as America’s sweetheart turned dangerously savvy business woman. Wait, shouldn't a successfully strategic business person be, oh we don't know, celebrated? But as is the pattern, when a woman exercises power, they almost always face backlash. 

Image credit: Pop Sugar 


So in 2020, Netflix premiered Miss Americana, the first in-depth, behind-the-scenes documentary of Taylor’s life during the years she disappeared. The film documents her battling an eating disorder caused by harmful representations and expectations of women’s bodies; her decision to finally take a public stance politically and fight for gay rights and women’s rights; and, somehow finding legitimate romance within that. It takes a respectable amount of strength to invite the world into the small slice of life they haven’t taken over already. But this is Taylor's approach since she started dropping real-life love stories into her songs; a sharing strategy that's built her a loyal and global fanbase. 

Image credit: Billboard 


5. (Trade)mark My Words

You may recognize this iconic short-hair style Taylor debuted just before the launch of her most successful selling album to date: 1989. The look will forever be synonymous with her breaking into the pop-genre world with a whopping seven synth-pop singles and grabbing the title for highest grossing tour of 2015. But 1989 was also foreshadowing for Taylor's efforts to own what she creates. 

Image credit: Entertainment Tonight

In January, 2015, many of Taylor's lyrics were filed with the U.S. Patent and Trademark Office, preventing the use of these particular phrases printed on anything from clothing, printed publications, recordings, and a whole cast of objects you could possibly put words onto. An initial reaction to this might be: who does she think she is, owning English words? But let us paint you a picture. You've worked your life to build a career in music, you've slaved over the right words for a high pressure album, you've put time and money into those words you wrote by your own hand, and a third party company uses your lyrics to then sell their own products. And as we know, association sells; just read up on the famous red sole shoe battle between Christian Louboutin and Yves Saint Laurent. A red sole equals a high end shoe. A recognizable lyrics equals a popular selling shirt. This is just her effort to own what she creates. 

Image credit: Wikipedia


6. Met Gala X Bleachella 

Finally, we’ve arrived at Bleachella. We are, of course, quoting Taylor’s now-deleted instagram post at Coachella with Lorde and Jack Antonoff sitting poolside, debuting freshly bleached bob. She really can pull off any style. Her platinum 'do' has since been her own song’s easter egg (your buzz cut and my hair bleached) which fans speculate depicts the night of the 2016 Met Gala, which Taylor was co-chair for. Her custom Louis Vuitton-designed look leaned into that year’s technology theme, with lace up sandals and an edgy look not seen on Taylor before. Call it a prelude to the darker wardrobe and marketing for 2017’s reputation and the beginning of Taylor purposely shattering the "America's Sweetheart" image the media gave her. 

Image credit: Vogue

7. She's "The Man"

“When everyone believes you, what’s that like?” Taylor asks in the lyrics of her single “The Man” from 2019’s album Lover. For the single’s music video, Swift completely transforms into a Wolf Of Wall Street high roller with a tendency to 'man-spread' and take names. Taylor directed the video and donned an impressive amount of makeup for the role, pinpointing gender stereotypes and the encouragement of toxic masculinity in the industry. She’s been in this business since she was 13; so she knows as well as anyone that the constant magnifying glass and scrutiny the public puts towards her love life is not seen when a male singer, for example, reaches the same amount of fame. “I’m so sick of running as fast as I can, wondering if I’d get there quicker if I was a man,” she sings. 

Image credit: Rolling Stone


8. Entering the Political Stage

The “You Need To Calm Down” music video is one for the books. There’s a cameo at every turn of the camera with appearances by the cast of Queer Eye, Ryan Reynolds, and Katy Perry. It’s a fun bop calling out homophobes and haters (which we all know Taylor has done before, queue “Shake It Off”) but it’s the first of her song’s to dial in on a specific human rights issue.

Image credit: Billboard

The video ends by calling viewers to support Taylor’s Senate petition to pass the Equality Act at the time in 2019. She also joined GLAAD’s “Summer of Equality” campaign urging the U.S. Senate to pass the act which ensures comprehensive protections against discrimination for LGBTQ Americans. You can read more about it here.  

Image credit: The Boston

9. A 19-year Old Hosts SNL 

In November 2009, a 19-year old Taylor hosted Saturday Night Live, her musical monologue of witty words fired at an ex are a forever pick-me-up when you need to remember your own power and make clever comebacks at the media’s portrayal of you - and as we’ve learned in this article, that's a constant effort for Taylor. 

 Image credit: Billboard 

10. To Apple, Love Taylor

It’s June 21st, 2015, and you’re an exec at Apple who just received a letter. You're presumably panicking because one of the most popular musician’s catalogue, which includes her hit new album 1989, isn’t going to be available on your streaming service, something you've promised your customer base. At least, this is how we imagine it played out. Taylor’s massively hit album 1989 has since returned to streaming platforms, but at this time, it was a dim prospect.

Image credit: Pinterest

That fateful morning, Taylor posted her open letter to Apple Music on her Tumblr (whoa, blast from the past!) detailing her issues with the fact that artists and labels would receive no royalties for their music during Apple Music’s three-month free trial. “Three months is a long time to go unpaid, and it is unfair to ask anyone to work for nothing...we don’t ask you for free iPhones,” the letter reads. The letter prompted an immediate response from Apple, because this is a woman with an incredible amount of influence. Their response read: “We hear you, Taylor,” and the rest is history.

1989 went on to win Album Of The Year and Best Pop Album at the Grammys. Pictured above is Taylor owning the Oscar photo booth in an Atelier Versace coral crop top and billowing hot pink skirt. This look is visually on theme with the bright colors of the 1989 tour wardrobe, and that expression is the look of someone who has protected the royalties of that album and the albums of many artists. 

11. "Big (reputation) Influence"

Taylor performed at the 2019 Time 100 Gala wearing a strapless pink and yellow J. Mendel dress and pairing the red carpet look with Lorraine Schwartz jewels and  Chloe Gosselin shoes. As per Taylor’s style, her instagram gave us major fairytale-"Love Story" vibes as she ran through the gardens in this flowing gown. A royal-esque fit makes sense for her given title of “Icon” at the event and being named one of the 100 Most Influential People of 2019 by Time

Image credit: E!Online




12. A Silence Breaker

Taylor was one of Time’s "Persons of the Year" in 2017 as part of their “Silence Breakers” issue. This article is a heartbreaking, inspiring, sickening, and all around groundbreaking piece spotlighting many anonymous, many famous victims of assault following the #MeToo movement. Spearheaded by the hashtag started by actor Alyssa Milano, the movement spurred unprecedented repercussions for harassment and assault at the hands of people in positions of power globally. 

Image credit: Time

In an interview with Time, Taylor opened up about her assault trial concerning a 2013 incident where a Denver radio DJ David Mueller reached under her skirt and grabbed her rear end. Mueller sued her for millions in damages after he was fired. She sued back for $1 and testified in a Denver court. After being asked by Mueller’s lawyer on the stand whether she felt bad for getting Mueller fired, she said: "I'm not going to let you or your client make me feel in any way that this is my fault. I'm being blamed for the unfortunate events of his life that are a product of his decisions. Not mine," (Time, 2017).

Taylor told Time “I figured that if he would be brazen enough to assault me under these risky circumstances, imagine what he might do to a vulnerable, young artist if given the chance," (Time, 2017). She won the case, and in turn, gave hope to countless sexual assault victims who are refusing to be silenced, who don’t receive widespread media attention, who don’t believe they can speak up.

Image credit: Time

13. Woman of the Decade

And we arrive at the 2019 Billboard Women In Music Event, where Taylor wore a navy blue jumpsuit with gold Oscar de la Renta embellishments to receive the award for Woman of the Decade. Taylor started out in Nashville in 2006 and since then has become one of the most successful musicians of our generation. She has five number 1 albums, done three global stadium tours, and broken numerous records, including her own, for album sales and awards won. At the event, Swift spoke about the obstacles she had to overcome as a woman in music and encouraged artists in the audience to keep working.

Image credit: E!Online

"I saw that as a female in this industry, some people will always have slight reservations about you. Whether you deserve to be there, whether your male producer or co-writer is the reason for your success, or whether it was a savvy record label." She said in her acceptance speech. "I saw that people love to explain away a woman's success in the music industry, and I saw something in me change due to this realization. This was the decade when I became a mirror for my detractors. Whatever they decided I couldn't do is exactly what I did….Whatever they criticized about me became material for musical satires or inspirational anthems...basically if people had something to say about me, I usually said something back in my own way."

Image credit: Glamour

She continues: "At that time I couldn't understand why this wave of harsh criticism had hit me so hard….And now I realize that this is just what happens to a woman in music if she achieves success or power beyond people's comfort level...I will say that in 10 years I've seen forward steps in our industry, in our awareness, our inclusion, our ability to start calling out unfairness and misconduct...And as for me, lately I’ve been focusing less on doing what they say I can’t do and more on doing whatever the hell I want."

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