Although most of us know her for her music career, it’s hard to deny that Taylor Swift has become somewhat of a fashion icon. From the football stands to her world-wide Eras tour, the “Tortured Poets Department” singer has proven time and time again she knows how to serve up an outfit that thousands will instantly want to emulate. Who else couldn’t stop fawning over her oversized, leather blazer and boots ensemble last fall, or her winning 2024 Super Bowl outfit?
Other times, though, Swift’s getup misses the mark. Hey, we all have that experience once in a while. With Swift, though, it’s a little more surprising considering she has stylists and an-almost unlimited pool of resources to draw from.
A word of clarification is necessary here, though. We love a person showing a little skin if that’s their proclivity, and dressing however they want. Women in particular get shamed to no end for following their sartorial bliss, and we are not about that. When we say “inappropriate,” we mean that the outfit is wrong for the event, or that it doesn’t flatter, or that the accessories were chosen poorly, or that things aren’t complementing Swift. So we’re taking a look at these rare moments where Swift looked less than perfect. From fan feedback to stylists lamenting clothing choices, Swift has failed our fashion expectations more than once.
At the MTV Music Video Awards in 2015, Taylor Swift wore a glittering houndstooth two piece set by Ashish. The top was cropped, and the pants were cut like joggers. Swift won video of the year for “Bad Blood.” While she won that night, her outfit was a miss. The sweatsuit-style outfit was inappropriate for such a big night, as it came off as super casual. In a discussion on all of Swift’s VMA looks, fans on Reddit in the r/TaylorSwift community got busy talking about her 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. Someone else said that Swift’s looks, especially her more complex red carpet looks, don’t deliver. “She never quite pulls it off,” they began. “There’s always something weird about her look.” Another fan had a sweet hypothesis. “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. “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!” Honestly, it’s not a bad point!
For the 2024 Grammys, Taylor Swift wore a white Schiaparelli gown with a bunched waist and a thigh-high slit. She paired the look with black opera gloves, black heels, and several silver and black necklaces. She also wore a black chocker with a clock set to midnight. She styled her hair to the side, with part of it tied in a loose braid. Unfortunately, Swift’s red carpet outfit was not well received by fans, who found that the whole ensemble didn’t work well together. Many felt her hair was too casual and undone for such a glamorous gown. Others found the cluster of necklaces too busy for a heavily-draped dress.
On the Instagram page taylorswiftstyled, people discussed why the ensemble was a miss. “It’s bad,” a fan began. “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 dress was a problem for someone else, too. “The dress looks like a bunch of extra sheets they didn’t know what to do with…” they wrote. There’s a lot going on in Swift’s red carpet wardrobe here, and rather than being harmonious, the pieces didn’t work well together.
We can’t knock Taylor Swift for wearing all denim, as the trend is everywhere now, but this outfit was off. For the VMA’s afterparty in 2023, Swift walked out in a denim playsuit by EB Denim, consiting 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. Her hair was half-up, half-down and she wore a heavy, dark wing for eye makeup and her signature red look. There was something about all of the elements here that just 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 hair was the killer here. “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.
In May 2023, Taylor Swift was spotted leaving a recording studio in New York City. She wore black, denim shorts, tan sandals, and a wide, boxy white blouse. The excessively loose top cut her shape in half, and made her appear squat in what was otherwise a totally fine, summertime outfit. According to the Instagram page taylorswiftstyled, the white top is the Gathered Hem Shirt by R13, which retails for $450, and the black shorts are the Crossover Short in Black, also by R13 and they cost $365. Normally, fans really like Swift’s street style, but people weren’t feeling this look. “$365 for the ugliest pair of shorts i’ve ever seen in my life,” someone commented. “Such bizarre shorts. Not my fav,” another wrote of the crossover shorts. Another fan felt like Swift’s outfit wasn’t appropriate for the outside temperature. “i’m convinced she never checks the weather before going out,” they added. So this casual look was not a win.
Sure, the Eclectic Grandpa trend is taking over niches of the fashion community, and sometimes it’s very cool. However, Taylor Swift stepped out in November 2023 in that style and the look didn’t land. 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 here, and created a chaotic palette. Her hair, worn straight and long, was too heavy around her face for a look that was already bulky. People really didn’t respond to this getup, and found it a failed attempt at the Eclectic Grandpa trend or the Professor look. “[T]he pants I hate the most. Idk who been dressing her lately,” someone commented on the Instagram page taylorswiftstyled. Another person joked that Swift was starting to dress like boyfriend Travis Kelce. “She is starting to make fashion choices like Travis lol,” they wrote. Another person hit a first with Swift’s style. “This may be the first time I’ve ever disliked one of her clothing items,” they wrote. There were too many brown tones to make sense of this ensemble.
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 definitely felt like an outdated fashion trend that we’re all trying to avoid. 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 this 2020 NME look, Swift could definitely have benefited from some professional help with putting together a sharper outfit.
