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.

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.

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.

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.

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.

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."

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.