Taylor Swift's Worst-Dressed Red Carpet Moments That We Just Can't Forget

Taylor Swift's pen is mightier than her stiletto heel. The multi-platinum singer-songwriter has never been regarded as a fashion icon. Instead, she's always been a musician first, famous for empowering songs and incisive love lessons. Her clothes have often worked as an enhancement to her art — another way by which she builds her brand and the narratives of her albums. In some ways, Swift's persona hinges on relatability, and her clothes have reinforced that message. At times, she's been caught in ill-fitting styles or outdated trends. Her red carpet choices have sometimes downplayed her stratospheric fame and wealth and instead have been a little ... well, odd.

Cookie Cohen is the creator behind the Instagram account @youbelonginthis, where she fantasy styles the pop star in archival vintage and cutting edge designers. Cohen sees Swift's style choices as a missed opportunity, one that occasionally emphasizes relatability at the expense of making it on the best-dressed list. "For red-carpet looks, I want simple, elegant, flattering — she constantly misses on all these marks," Cohen told Business Insider. Below, we explore a few of the memorable moments when Swift really missed the mark.

Still just 16, Taylor Swift appeared at the Country Music Awards in a black, mermaid-silhouette dress that didn't feel quite right for the red carpet of twang. Instead, the dress was overly formal, with its satin-y, prom-coded texture and elbow -ength gloves. The black color is harsh on the fair singer and leaves her looking old despite her youthful persona. The selection is also unexpectedly vampy for an artist who has largely built her career on themes of girlhood and innocence. Here, Swift appears every bit the ordinary teenage girl — one who hasn't yet adjusted to life in the spotlight or embraced celebrity styling.

The long-sleeved, blue Mary Katrantzou romper that Taylor Swift wore for the 2014 MTV Video Music Awards was a strange choice for the tall, thin star (though it suited the color palette and sleek aesthetic of her "1989" album cycle). It's a peak example of a moment when Swift was dressing for the era rather than choosing a flattering red carpet look. More notably, the short cut on the bodysuit seemed to disrupt the lines of the star's frame, shortening her and serving an unexpectedly casual look for a high-profile VMAs.

Perhaps Swift's most notorious look, the silver Louis Vuitton mini dress with knee-high gladiator sandals suited the "Manus x Machina: Fashion in an Age of Technology" theme of the 2016 Met Gala, but it did the pale pop star no favors. The tech-forward ensemble was a dramatic turn from Swift's more romantic styling and felt odd on a singer who has not particularly focused on experimental, fashion-forward dressing. The futuristic look featured a short, bleached bob and dark lipstick, and many critics felt the overall effect was far too harsh for the singer and that it wasn't one of her best short hair moments. Of course, Swift's brief stint as a platinum blonde became almost ironically iconic, and the micro-era has come to be known to Swift fans as "Bleachella." Perhaps, on the red carpet, enough wrongs do make a right.

The plaid ensemble that Taylor Swift wore to the 2020 Sundance Film Festival premiere of the documentary "Miss Americana" was an unexpectedly serious vibe for the star. Though ostensibly set within the whimsical and pastel era of "Lover," the patterned set almost seemed to age the youthful star and introduced a sartorially confusing retro twist to her aesthetic of the moment. Meanwhile, the color palette felt poorly suited to the glamor of the red carpet.

Perhaps the plaid print is a reference to noted Brit Joe Alwyn, her then-paramour. But, the pop singer doesn't so much seem to be wearing the jumpsuit–trench coat combo as the onslaught of busy pattern seems to be wearing her.

Taylor Swift appeared in a short, denim skater dress for the 2023 MTV Music Video Awards afterparty. While the blue color palette and copious blinged-out accessories were consistent with the glittering aesthetics of the "Midnights" era, the cut of the poorly fitted dress interrupted the statuesque singer's long lines. While much of the album cycle seemed to celebrate glamor, the "Bejeweled" singer reached, unexpectedly, for denim, a casual texture that seemed at odds with the celebratory significance of the night and the opulent sparkles that had been associated with the era. The designer behind the ensemble, with its corset top and pleated skirt, was EB Denim. That night, Swift celebrated her fourth Video of the Year award — she just didn't take home a statue for Best Dressed.