6 Taylor Swift Outfits That Just Didn't Work

Although most of us know her for her music career, it's hard to deny that Taylor Swift knows how to rock a fashion trend. Whether she's in the VIP box of a football stadium or on stage for one of her world-wide Eras tour shows, the "Tortured Poets Department" singer has proven time and time again she knows how to rock an outfit that thousands will instantly want to recreate themselves. Who else couldn't stop fawning over her oversized, leather blazer and boots ensemble last fall, or her winning 2024 Super Bowl look? 

Other times, though, Swift's getup misses the mark. Hey, we all have that experience once in a while. With the A-list superstar, though, it's a little more surprising considering she has stylists and a near-unlimited pool of resources. From bizarre color palette choices on the red carpet, to awkward attempts at nailing TikTok trends, let's take a look at these rare moments where Swift looked less-than-perfect. 

Taylor Swift's "1989" era was all about bringing the glitz and shine to her looks, and this was no better evidenced than at the 2015 MTV Music Video Awards. Up until then, the public had gotten used to seeing Swift in long, elegant gowns for the occasion. But for this event, she decided to switch things up and wore a glittering houndstooth two piece set by Ashish. The fitted top was cropped at the ribcage, and the pants were cut like joggers. 

Although the houndstooth pattern was fun, the sweatsuit-style getup seemed inappropriate for such a big night, as it came off as super casual. In one photo of her accepting the award, she appears next to several people in suits, which made her stand out like a sore thumb. The look even sparked some discussion on a Reddit thread about her overall sense of style. "Okay I love her but man. She has more fashion misses than hits. The majority of the outfits have the right concept but the execution is off," a fan commented. Another hypothesized that the look may have been an attempt to nail edgy runway style, but that it didn't quite work. "My personal theory is that she's a big nerd (which is why I love her so much) and the high fashion is something of an effort for her," they speculated. 

Fans blamed Swift's longtime stylist, Joseph Cassell Falconer for the fashion fail. "I've made this comment several times before, but she needs a new stylist," another said. "JCF has been dressing her for YEARS and his old-white-man-ness is really showing. She needs someone with fresh talent and fresh eyes!" 

High glam doesn't always guarantee elegance. Though Swift has a solid track record with looking fabulous in lengthy dresses at the Grammys, things took a turn at the 2024 event. That year, Swift took a risk by opting for a full-length, white Schiaparelli gown with a bunched waist and a thigh-high slit. The ensemble was a bit of an unusual choice for Swift, especially as she paired it with long, black opera gloves, black heels, and several choker necklaces. In some ways, it seemed she was trying to make herself look as if she stepped out of a black and white film, but instead, it looked more like she come straight from a costume party.

Unfortunately, the look left many fans disappointed. Some found the loose braid was too casual and undone for such a glamorous gown. Others found the cluster of necklaces too busy for a heavily-draped dress. "It's bad," wrote one commenter on taylorswiftstyled. "Her hair looks unkempt and probably should have been up and the dress gives early aught prom vibes. Too much. Not flattering." Another person commented, "I like the dress but I don't like the styling." The heavy fabric was also a problem. "The dress looks like a bunch of extra sheets they didn't know what to do with..." they wrote. 

We can't knock Taylor Swift for wearing all denim, as the denim-on-denim trend is everywhere now. However For the VMA afterparty in 2023, her attempt at being hip made her look like she was heading to a backyard barbecue. Swift walked out in a denim playsuit by EB Denim, consisting of a pleated mini skirt and a tank top. In an attempt to glam it up, she paired the look with silver, platform sandals and several necklaces.

Unfortunately, there was something about all of the elements that didn't fit for fans. "Tbh I hope taylor change her stylist, it's not that bad but it could be wayyy... better, I like her casual style more," someone commented on the taylorswiftstyled Instagram page. "Im really not feeling this dress. A no for me," another added. For someone else, the half-up, half down hair was the killer. "The hair is giving 2007 Billy Ray Cyrus," they wrote. Ouch! "I wish the hair would've been different," someone else added in reference to this VMA's afterparty look. While the shoes and denim were individually nice, the whole combination here was too busy, and Swift's long, mullet-style hair was too heavy.

It's safe to say that Swift's street style has become increasingly more relaxed over the years. Where in the 2010s she may have worn super-trendy outfits you'd find on a tumblr fashion blog, 2020s Taylor appears to be all about comfort. In May 2023, the singer was spotted leaving a recording studio wearing black denim shorts, tan sandals, and a wide, boxy white blouse. Oversized clothing may be in, but in this case, the excessively loose top cut Swift's torso in half, and made her appear squat. But what really ruined the look for fans was the crisscross black jorts, which, according to the Instagram page taylorswiftstyled, retail for nearly $400. "$365 for the ugliest pair of shorts i've ever seen in my life," someone commented on taylorswiftstyled. "Such bizarre shorts. Not my fav," another wrote of the crossover shorts. Another fan felt like Swift's outfit wasn't appropriate for the New York weather. "i'm convinced she never checks the weather before going out," they added. 

Sure, the Eclectic Grandpa trend may be taking over the TikTok community, and sometimes it's very cool. Unfortunately, Taylor Swift's attempt at this look proved that some aesthetics aren't for everyone. She wore chunky brown loafers with wide-leg, brown trousers, and an orange and lighter brown sweater by GANT. The many tones of brown were confusing, and when combined with the greyish brown trousers, it created a chaotic palette that gave more 1990s librarian than it did off-duty pop star. Swift's light spring complexion (which typically looks great against bright , cool colors and pastels) also appeared washed out against the numerous earth tones. "This may be the first time I've ever disliked one of her clothing items," wrote one fan on Instagram. Another joked that the look was an indication she may be dealing with the boyfriend effect. "She is starting to make fashion choices like Travis lol," they wrote. 

Taylor Swift attended the NME Awards in London in 2020, and won Best Solo Act in the world. For the event, Swift wore a very unusual two-piece suit made up of pinstripe shorts and a matching wrap blazer, with part of the top as an off-the-shoulder blouse. The lace-up white booties also seemed outdated, which was surprising for a star who is usually on top of the trends. The slouchy shoulder looked sloppy, and the boots cut Swift's legs off, making the outfit shorten her silhouette. Repeated outfits like this one led one person to turn to the r/SwiftlyNeutral group on Reddit and write the controversial heading that Swift actually has a bad sense of style, and really needs a new stylist. They wrote, "From the mismatch of pieces, to the terrible shoe choices... since it doesn't seem to come naturally for her, I would love to see her hire a decent stylist and SERVE some looks," they wrote, adding, "everyone on the main subs constantly talks about how great her looks are, am I missing something??" 

People were quick to agree. "[I] feel like it's a good example of why a stylist is important," someone replied. "[M]ost of these aren't TERRIBLE but a different makeup/shoe/hair choice could fix everything and i don't understand why she doesn't have a stylist correcting the little things..." In cases like the 2020 NME look, Swift definitely could have benefited from some professional help with putting together a sharper outfit.