The Best And Worst Outfits Worn By Taylor Swift

Whether she's rocking a Kansas City Chiefs sweatshirt or donning a sequin mini dress, Taylor Swift and her sartorial choices are always a topic of discussion. While she now croons about "dressing for revenge," Swift once revealed that it's her famous gal pals who inspire her the most when it comes to fashion. In a 2014 interview with ASOS Magazine, she explained that they are the true force behind her style decisions. "When I'm getting dressed, it's always based on what my friends will think," she told the magazine (via Glamour). "They are my number one priority, and the opinions of girls are more important to me at this point in my life."

However, the singer went on to say that, at the end of the day, comfort is the main factor she looks for in clothing. "Being comfortable means that no one's going to be able to pull a fast one and take a picture of me that they'll deem to be embarrassing," she declared. Arguably, this mindset is a huge part of her overall appeal. When taking a quick glance at candid paparazzi photos of Swift, she looks the way the rest of us would while waiting for a coffee in the Starbucks line or going on a morning power walk. That said, most of her event looks are meticulously put together. Let's take a look at the ones that worked — and the ones that didn't.

Worst: Her first ACMs dress

Taylor Swift first stepped onto the scene in 2006 when she released her single titled "Tim McGraw." She emerged as a 16-year-old country singer who had the look of a young Nashville sweetheart. "I wrote [the song] in my freshman year of high school," Swift told CMT back in 2006. "I got the idea in math class. I was just sitting there, and I started humming this melody. I kind of related it to this situation I was in." She continued, saying, "I was dating a guy who was about to go off to college. I knew we were going to break up. So I started thinking about all the things that I knew would remind him of me. Surprisingly, the first thing that came to mind was that my favorite country artist is Tim McGraw."

The debut hit song earned Swift a spot at the 2006 Academy of Country Music Awards, where she appeared on the red carpet dressed in a boho handkerchief hem dress paired with bedazzled cowboy boots. It's hard to picture Swift wearing something like this today — especially on the red carpet. Thankfully, the singer has made an incredible transformation since her first ACM Awards appearance.

Best: The 2013 CMAs red gown

In 2013, Taylor Swift was just 23 years old and already defying the odds and crushing the music industry so hard that she became the second-ever performer to win the Country Music Association's Pinnacle Award at the CMAs. The win moved her to tears as some of the biggest names in entertainment commended her on the achievement. The award was created to celebrate "an artist who has achieved both national and international prominence through concert performances and record sales at levels unique in country music."

Swift attended the event in an Elie Saab floor-length red gown that featured meticulous embroidery and a fitted waist. Combined with Swift's hair and makeup, the dress subtly channeled Old Hollywood glamour and evoked the classic spirit and boldness of rich shades of red. In fact, after the ceremony, Today named Swift as one of the top four best-dressed in attendance, alongside Carrie Underwood, Miranda Lambert, and Kacey Musgrave. The dress was also a nod to her 2012 album "Red," which helped the singer break into the pop music scene.

Worst: The prom dress/wedding gown look

Taylor Swift's winning speech at the 2008 ACMs is considered to be one of her best. "There are so many people that deserve to be thanked for this," an excited Swift said. "But I'm just gonna thank one and that's the person that used to love to go to lunch with her friends and cook dinner for her family and sleep in her bed every night, and she gave that all away and left it all behind to go on the road with her 16-year-old daughter. Then she was sleeping in rental cars and in airplanes with her mouth hanging wide open 'cause she was so tired. And so, Mom, thank you so much. I love you. This is for you."

As warm-hearted as the speech was, though, it was impossible not to be distracted by Swift's gown. The white, floor-length dress included a fitted, glistening bodice, as the waist then cascaded down into a flowy chiffon. It was reminiscent of an early 2000s prom dress or wedding gown — two looks that should be avoided on a red carpet at all costs.

Best: The 800-hour ensemble

In 2016, Taylor Swift's "America's sweetheart" image was becoming more and more tarnished by media gossip regarding her infamous relationships and dramatic feud with Kanye West and Kim Kardashian

"The thing is, whether she's right or wrong in these things, she's coming across petty and argumentative, and they're not good looks for her," Jem Aswad, senior editor at Billboard, told USA Today. "For someone who guards and constructs her image as meticulously as she does, it's a rare case of things slipping out of her control." So, in typical Swift fashion, she let out her emotions in her music. Thus, the album "Reputation" was born, along with its hit single "Delicate."

Fast forward to 2018, Swift walked the red carpet at the Billboard Music Awards in a jaw-dropping Versace dress. The pale pink gown, laced with feather detailing and chiffon accents, displayed a thigh-high slit and was coordinated with Casadei heels. The dress reportedly took a whopping 800 hours to create. The best part of all? It was a simple nod to her "Delicate" single. "Thanks [Versace] for this delicate dress," the songstress wrote on Instagram.

Worst: The dreaded onesie

One thing many can agree on about Taylor Swift is that she has fantastic legs. Her famous stems have been dubbed epic, and they are a part of her signature look. In fact, rumors (which Swift later said were untrue) claimed the singer had her legs insured for $40 million. "It seems like a ludicrous sum, but if something was to happen to her legs, Taylor wouldn't be able to give her signature stage performances," one source told the Daily Mail in 2015. "Her $200 million career would be in big trouble."

As much as Swift likes to show off her famous legs — and as much as fans rave when seeing them — that doesn't mean leggy outfits are an automatic win. The singer-songwriter's ensemble at the 2014 MTV Video Music Awards is proof of that. There, she donned a long-sleeved blue Mary Katrantzou romper that was so short that it looked like a baby onesie. What made matters worse and even more juvenile? The romper was embroidered with letters in shades of olive and gold.

Best: That black Versace gown

Taylor Swift made a surprise appearance at the 2019 Golden Globes when she presented the award for Best Original Song to the winner, Lady Gaga. It was Swift's first award show in months, stepping onstage with "Cats" co-star Idris Elba. While social media was soon flooded with speculations of a possible Gaga/Swift collaboration, it was Swift's mermaid-style black Versace gown that earned the most attention among fans. Users began tweeting about the scale-like look of the dress, thinking it may have been hinting at a mermaid theme in her upcoming album, as Glamour reported.

When the "Lover" album was finally released, there wasn't much of a mermaid theme — but whatever it was that prompted Swift to wear the Versace gown, we're here for it. The stunning chevron pattern glistened as it revealed a sheer layer of skin underneath, while a classic Swift thigh-high slit stole the show. There was, perhaps, one subtle nod to her upcoming album in the outfit, though. Each of her drop-dangle earrings featured seven diamonds — and "Lover" was the singer's seventh album.

Worst: The Met Gala dress that screamed 'Charlotte Russe'

Taylor Swift went through somewhat of an awkward fashion era between her "1989" album in 2014 and her "Reputation" album in 2017. Many contend that "1989" solidified Swift as a true pop singer, so her transition from bubblegum pop princess to the edgier "Reputation" image was shocking for some.

In 2016, she graced the cover of Vogue with short, bleached hair and stepped out with the same 'do a month later at the Met Gala. Here, she took the grungy style a little too far. While the Met Gala is, of course, known for unusual ensembles — and that year's theme was "Manus x Machina: Fashion in an Age of Technology" — fans still agreed that this look was a miss. "T swift looking ravishing in Charlotte Russe atelier," one fan tweeted. Indeed, Swift's outfit came off looking cheap. She could've donned something much more high fashion and more suited to her style.

Best: Taylor Swift's mossy (or should we say money?) green gown

Olive green isn't a color we see Taylor Swift in particularly often. However, she wears it well. In 2019, Swift attended the 2019 American Music Awards in a custom olive green Julien Macdonald dress that showed off hints of skin with the help of a pair of black over-the-knee boots — and the fans couldn't get enough.

"Taylor really said 'I am money' tonight huh?" one person tweeted. "Taylor Swift wearing green — the colour of envy, snakes, money — at the #AMAs," wrote another fan with an added green heart. Yet another chimed in, "Taylor Swift came dressed as money to the #AMAs — the $7.9 million owed to her by Big Machine Records, to be exact."

Swift did incorporate a little green into her "Eras" tour — namely the iconic green chiffon Alberta Ferretti folklore dress. However, we'd love to see her in another ensemble like this 2019 gown.

Worst: The rainbow Reputation dress

Taylor Swift's "Reputation" album was met with a lot of mixed reviews when it dropped, and the same can be said about her choice of outfits to promote the album. In 2017, she posted an album promo picture on Instagram wearing a sequin rainbow dress with a matching jacket by Ashish. "Let the games begin," she wrote.

Initially, some thought that this was Swift's way of showing support for the LGBTQ+ community. "Taylor Swift wearing a rainbow dress indicating she's supportive of the lgbtqa+ community I love one (1) woman," one Swiftie remarked (via Teen Vogue). However, others shut these claims down quickly, replying with comments criticizing Swift — and that ensemble. "Don't call Taylor Swift the next Gay Icon just cause she wore an ugly rainbow dress. Think about it, when did Taylor ever speak up or contribute anything to the lgbtq community?" one wrote. Another added, "This is the s*** you'd get sent home for on RuPaul's drag race."

On top of it all, the outfit was paired with distracting gold basketweave booties. This look officially goes down as one of Swift's worst to date.

Best: Taylor Swift's sparkly Toronto International Film Festival gown

After the 2022 "Gilded Glamour" themed Met Gala, the glitzy golds seen on those in attendance became a mega trend of the year. Gilded glamour represents the golden age of America, a period that spanned from 1870 to 1890. It was a time when industrialization was at its peak, and the country saw a forthcoming of modern inventions like the telephone, the lightbulb, and heavy machinery. The newfound success represented prosperity and growth — and so did everyone's clothing.

As an avid fan of American history, we would expect nothing less of Taylor Swift than for her to jump on a trend rooted in the past. Channeling all of the glitz and glamour of days gone by, the singer emerged at the 2022 Toronto International Film Festival wearing a gold mirror Louis Vuitton dress. Everything about the look was captivating, from Swift's long, luscious locks all the way to the intricate coin detailing on the straps.

As Catherine Kallon of Red Carpet Fashion Awards noted , "I love this [look] for Taylor. It has a feeling of 'let me reintroduce myself.' I like how her makeup was kept simple to allow the dress to shine (literally), and that this is not another mini dress."

Worst: Taylor Swift's unfortunate ruffly moment at the 2019 Billboard Music Awards

2019 was an odd year for style trends. Biker shorts became an everyday staple, Michael Myers-esque utility jumpsuits were considered high fashion, and dramatic capes somehow made their way onto the runway.

Even weirder, ruffles made a surprising comeback, appearing everywhere from sleeves to pant legs. "They're a sign of leisure," Jonathan Walford, co-founder and curatorial director of the Fashion History Museum in Cambridge, told Fashion that year. "Ruffles are not something you wear to make yourself more useful. They're unnecessary frivolities that you add to your clothes."

Taylor Swift herself embraced the trend when she appeared at the 2019 Billboard Awards dressed in a purple mini dress. Unfortunately, it was a look that ruffled some feathers. Mirror crowned Swift with the title of "worst dressed" at the event and even went on to label the ensemble as "gaudy." 

Best: Her midnight blue 2023 Grammys dress

Sure, Taylor Swift has had some fashion misses — who hasn't — but she is the indisputable queen of coordinating her outfits to her albums. And her 2023 Grammys dress may just be our favorite homage yet. The sparkle-encrusted deep blue two-piece ensemble featured a long-sleeved, mock neck top, a high-waisted skirt that swept into a train, and navy blue and white crystals sewn throughout. Designed by Roberto Cavalli, the dress truly looked like "Midnight Rain," one of the tracks on her 2022 album "Midnights."

A dress with this level of glamour doesn't need much when it comes to accessories. Swift chose to keep it simple with only three pieces of jewelry. She sported $3 million worth of Lorraine Schwartz jewelry, including 136 carats of purple sapphires, blue sapphires, and white diamonds. Her nails were manicured with a matching metallic blue, and she complimented the entire look with a wispy bun, her signature red lip, a classic cat eye, and a cool-toned smokey eyeshadow on her lids.

Worst: Her 2022 VMAs after-party romper

At the 2022 MTV Video Music Awards, Taylor Swift surprised fans by announcing the date of her new album — October 21 — when she accepted the Video of the Year award. She informed fans that she'd let them know more details after the ceremony ... at midnight. "This is a collection of music written in the middle of the night, a journey through terrors and sweet dreams," she revealed at midnight on Instagram (via Teen Vogue). "The floors we pace and the demons we face. For all of us who have tossed and turned and decided to keep the lanterns lit and go searching — hoping that maybe, when the clock strikes twelve, we'll meet ourselves."

But before those details went public, Swift attended the VMAs after party wearing a look that hinted at — or screamed — the "midnight" theme of her album, she wore a royal blue spaghetti strap romper slathered with sparkling silver stars across the bustier-style bodice. To accessorize, she opted for a shaggy white faux fur coat and silver platform shoes. Unlike her deep blue Grammys gown, this look was more Americana, less midnight. Overall, this look was just too much.