5 Times Taylor Swift Should Have Been On The Worst-Dressed List

Taylor Swift is often admired not only for her singing but for her impeccable style. However, it's not always a hit for Miss Americana. Even the stylish singer has her off days when it comes to her wardrobe choices. Throughout her career, Swift has had moments when her fashion turned heads — for all the wrong reasons.

From her early days of curly hair and cowboy boots to ultra-short rompers and sleek two-piece suits, Swift has undergone a remarkable sartorial transformation and fearlessly explored fashion, switching up her style with each of her musical eras. The award-winning singer has tried several styles, which each reflect her personal and artistic growth.

But being constantly in the spotlight means her fashion faux pas have been impossible to miss. While she often dazzled with some of her past bold looks, there were a few outfits that just didn't make the cut. These fashion blunders, subtle or not, could've easily landed Swift a spot on the worst-dressed list.

In 2015, Taylor Swift ditched her elegant gowns and opted for an elevated athleisure look at the MTV Video Music Awards. The singer rocked a sparkly houndstooth two-piece outfit by Ashish. The look featured a cropped top and jogger-cut pants in hues of gold, silver, and bronze. Swift matched the sequined getup with metallic Christian Louboutin Pumpstagram heels.

While the pattern on Swift's ensemble screamed glitzy, the sweatsuit style seemed inappropriate and too casual for such a big event. Since Swift is typically known for wearing fancy dresses at award shows, her choice of a bold pantsuit was definitely a big shakeup in her style. For instance, Swift wowed in a form-fitting black gown with a plunging neckline at the 2013 VMAs. And who could forget her full-length, one-shoulder gown at the 2009 VMAs — the one she wore when Kanye West infamously interrupted her acceptance speech? These gowns exuded elegance, offering a stark contrast to the edgy vibe of her pantsuit look.

Taylor Swift appeared to take inspiration from Britney Spears' iconic 2001 denim dress when she hopped on the denim-on-denim trend. The "Cruel Summer" singer turned heads in an upcycled EB Denim corset mini-dress at the VMAs after-party in September 2023. Swift changed out of her daring Versace gown into a pleated denim skirt and tank top. She completed her outfit with sparkly platform sandals and layered necklaces. The look doesn't seem to hit the mark, though. While the short dress was hip, it seemed too casual for a star-studded after-party in New York City. Not to mention her half-up, half-down hair, which some Instagram commenters compared to 2007 Billy Ray Cyrus.

This wasn't the first time Swift rocked a denim dress. In the behind-the-scenes footage from her "I Can Do It With a Broken Heart" music video, the singer is shown rehearsing in a denim exercise mini-dress from Wiskii, which immediately sold out after Swifties saw it.

Taylor Swift, just like any millennial, is always up-to-date with the latest trends. The singer once tried the "eclectic grandpa" look, a fashion aesthetic that quickly went viral on TikTok in 2024. The trend features old-school items a typical grandfather would wear, such as corduroy slacks, woolen knits, mohair cardigans, and loafers. Brown tones and earthy shades are the go-to colors, along with retro patterns and prints that complete the nostalgic vibe.

In November 2023, Swift was spotted in New York City in her eclectic grandpa attire. The singer donned a pair of chunky loafers, wide-leg trousers, and a vintage-inspired orange and brown sweater by GANT. She also rocked her signature full bangs, perfect for that vintage look. While Swift's outfit exuded old-fashioned vibes, it didn't seem to hit the same way as others' takes on the popular TikTok trend. One Instagram user even joked that Swift may be dealing with the boyfriend effect, making fashion choices like Travis Kelce.

In 2008, Taylor Swift wore wrinkled attire that left some people scratching their heads. The singer attended the Young Hollywood Awards in a creased purple dress that matched her dark smokey eye. She wore her hair styled in a side-swept ponytail. While the wrinkles may have been a deliberate fashion statement, they definitely gave Swift a disheveled appearance. Not to mention, the dress looked like it could have used some steaming.

That wasn't the only head-turning outfit Swift sported in 2008. The year saw a few more questionable dresses, including that white dress she wore at the Academy of Country Music Awards, which could have easily been mistaken for a wedding gown. Then there's the purple corset dress she wore at the Grammy Awards, which featured an excessively long corset and chiffon bottom. The same year, Swift attended the CMT Music Awards in a maroon dress with weird-looking ruffles at the bottom. While it may have been trendy at the time, the style was definitely not one of Swift's best looks.

In 2013, Taylor Swift sported yet another interesting ensemble that could've easily landed her on the worst-dressed list. During her Brit Awards performance, the "Fortnight" singer wore a lacey, poofy white dress resembling a wedding gown. The eye-catching frock had a rather odd shape, particularly the bottom part. It's hard to tell what the inspiration behind the strange-looking dress was, but it definitely exuded old-fashioned bride vibes. Fortunately, Swift managed to redeem her look when she ripped off the conservative dress mid-performance. Beneath the white gown, the singer rocked a black, low-cut lace top with leather pants and knee-high black boots.

This wasn't the singer's only white dress that made quite an impression. Swift graced the 2024 Grammys red carpet looking like a sexy bride in her racy, full-length white gown. The draped dress was a custom look by Daniel Roseberry for Schiaparelli, featuring a high-leg slit and dramatic train. While the dress looked classy, the overall ensemble was a bit unusual, especially with the long, black gloves and chokers that Swift wore as accessories.