Taylor Swift's Worst Outfits From Each Of Her Eras

Even if you absolutely adore Taylor Swift's music (and her lyrics that sound like they were plucked from a vengeful 15-year-old's diary), you have to admit that when it comes to fashion, Swift's outfits don't always slay. Sure, she rocks those cute sequin leotards on stage when she's touring, but out in the real world, Swift can't seem to put a look together to save her life. Swift — just like her BFF Blake Lively, who unfortunately prides herself on not using a stylist — is proof that money can't buy taste. 

Although it's been speculated that Swift's lack of fashion sense is part of her brand — after all, much of what she does is calculated — Swift has days where her bad style actually reaches new heights of awful. While compiling all of Swift's unstylish outfits from each of her eras would be a months-long project, we chose to keep things short and simple by focusing on her 'fits that have been, well, something else to say the least.

At 34 years old, Taylor Swift may be more mature in "The Tortured Poet's Department" era of her life, but her style is still back in the 1990s — and not even in that cool Y2K fashion way. At the MTV Video Music Awards in September 2024, Swift wore a yellow plaid ensemble with black leather gloves that wrapped up her arms. The electrical-tape look was extremely distracting and overall the outfit wasn't her best.

In true Swift form, she also changed her outfit halfway through the night, opting for a custom-made Monse dress. It was a choice that fans saw as an Easter egg for her song "Down Bad," but unfortunately prioritized narrative over style. 

When Taylor Swift attended the 2022 American Music Awards in November, she wore a gold bedazzled jumpsuit that left much to be desired. In fact, if we jump ahead to one year later, Blake Lively wore something very similar and just as bad during New York Fashion Week in September 2023. Although Swift won six awards that night for "Red (Taylor's Version)," it's hard not to wonder what was going through her head when she left her house in this outfit.

It's one thing to find a great print and make it your whole personality for a night, but it's an entirely different thing when you find an unfashionably retro print and optimistically think it's going to work. In January 2020, Swift attended the Sundance Film Festival for the premiere of her documentary "Miss Americana" in a grey and white jumpsuit with a matching calf-length trench coat. 

Not only is this print way too loud for the monochromatic look — her heels were also sucked into this nightmare of an outfit — but it's a choice that seems strange considering the name of the documentary. Of course, not everyone has mastered dressing for their films like fashion icon Zendaya, but you'd think someone might have tried to talk Swift out of this debacle.

In August 2019, Taylor Swift released her seventh studio album, "Lover." Just a few months later, she attended the Billboard's 2019 Women in Music ceremony wearing a navy blue jumpsuit covered in golden chains. It's a confusing look, to say the least, and a strange choice for a woman who had, at this point, already achieved both professional and financial success. This 'fit is a little too department store for us, not to mention the fact that it doesn't match the gauzy, romantic aesthetic of the album.

Taylor Swift wearing something that most people with a mirror at home would never wear? You better believe it! The aqua, alphabet-print romper Swift wore to the 2014 MTV Video Music Awards in Los Angeles was paired with burgundy peep-toe booties that not only didn't match, but didn't even vibe aesthetically. 

Considering this was the year "1989" was released, Swift had the opportunity to play with those numbers in her outfit choice, but instead went with random lettering of all things. Similar to what she wore in 2020 for the "Miss Americana" premiere, Swift missed an opportunity to dress for the moment.