Taylor Swift's Worst Outfit Fails Since Dating Travis Kelce

Swifties witnessed the dawn of a new fashion era for Taylor Swift when she began dating Travis Kelce in 2023 — and some of what they saw likely left them feeling a bit confused about her clothing selections. Swift's wardrobe has evolved, and her football-playing boyfriend's career provided her with a fresh clothing category to explore: the game-day outfit.

But while Swift has been regularly showing up at Arrowhead Stadium to cheer for Kelce in Kansas City Chiefs sweatshirts and puffer jackets, she has also been promoting her album, "The Tortured Poets Department." The dizzying dichotomy between the world of rowdy, brewski-guzzling bros and the one evoked by her 11th studio album's title — one where brooding literary geniuses spend a dark and stormy night slowly sipping absinthe in a cavernous manor — has proven to be eyebrow-raising at times.

Perhaps the collision of her love life and career helps explain some of Swift's more puzzling outfits, such as the plain red sweater she wore to the AFC Championship in 2024. She scored a few points for choosing a top from her pal Gigi Hadid's brand, but it was an underwhelming look. "My style advice to other girls is to be experimental but always have a 'home base' and stick with your comfort style," she once told Glamour. So, maybe she was having a hard time deciding what to wear, threw her hands up in frustration, and decided to at least be comfortable. Whatever the case may be, she's done far worse than playing it safe with her style since she started dating Kelce.

When fans first heard Taylor Swift singing about wearing a dress in "Today Was a Fairytale," the gown above probably wasn't what they pictured (although she does go on to say that she "looked like a mess"). In November 2024, Swift hit the streets of NYC in an off-the-shoulder Vivienne Westwood gown with a princess-y silhouette, save for the knee-length skirt that made the proportions feel off. The gown's corset top was splashed with various overlapping colors, while the blue and beige stripes made it look like the A-line skirt and bodice definitely didn't belong together.

The psychedelic color scheme is what you might get if the fairies from Disney's "Sleeping Beauty" visited neighboring Wonderland and sampled some of its fantastical fungi before engaging in their iconic ballroom battle over what color Princess Aurora's dress should be. In other words, Swift was likely trying to bring a little whimsy to her wardrobe, but what she gave us instead was a bad trip.

Some internet naysayers deemed the colorful frock one of Swift's worst-ever looks, and her styling didn't help. Her gold pendant necklace was clunky, and her purple velvet Aquazzura sandals were a bit too sumptuous for the unusual gown, which was screaming for some accessories and footwear to make it more punk than princess. Only in her wildest dreams can Swift expect fans to say that they remember her "standin' in a nice dress" in regard to this look.

Taylor Swift wore the color of envy often after the sidelines of her boyfriend's football field became her new stomping grounds. She was wearing green at the 2024 Golden Globes when she had an icy reaction to an NFL joke, but that slinky sequined gown was arguably one of the best looks she's worn since Travis Kelce entered the picture. When she stepped out in another shiny green dress a few days later, it was less of a success.

For a night out in Brooklyn with a group that included one of Swift's closest friends, Blake Lively, the "Christmas Tree Farm" singer wore a green crushed velvet dress from Little Lies. It was inoffensive on its own, but she decided to pair it with thigh-high Jimmy Choo x Jean Paul Gaultier boots. Due to the boots' brown color, Swift ended up resembling a tinseled-up Christmas tree with a tall trunk. If she were hanging out with Lively's former "Gossip Girl" co-star Taylor Momsen in Whoville, the Grinch definitely would have tossed Swift in his sack along with the Whos' holiday decorations and roast beast. Even over on the Taylor Swift subreddit, where she can do no wrong, this festive 'fit had some Swifties saying, "Bah humbug!" because her footwear was ill-fitting and didn't complement her dress.

Then there were the scaly Easter eggs slithering around on Swift's boots. Thanks to Swift's infamous feud with Kanye West and Kim Kardashian, snakes and the color green are indelibly linked to the "Reputation" era. Swift's boots featured a snake pattern, prompting speculation that she was using her clothing to signal that "Reputation (Taylor's Version)" was on its way. However, this turned out to be a fashion fake out, as fans got "The Tortured Poets Department" instead.

In January 2024, Taylor Swift had a girls' night with Brittany Mahomes, the new bestie she acquired when her relationship with Travis Kelce made her an official WAG. The pair headed out to Nobu in NYC, where they were joined by model Cara Delevingne. Mahomes channeled Cher Horowitz in gray houndstooth separates; a boxy cropped coat and matching mini skirt. But it was Swift who wore one of the "Clueless" heroine's favorite brands. In retrospect, her Alaïa dress was teasing the Emily Dickinson vibes in her "Fortnight" music video, but there were some glaring issues with her garb.

With its baggy top and billowy sleeves, the dress resembled a garbage bag. It didn't seem to fit Swift properly, and she also left its mutton sleeves unbuttoned, killing its distinctive Victorian vibe. Instead of elevating her ensemble, the gold accessories she wore with her LBD drew attention to its sack-like quality; It's like she threw on the layered chain belt to give it some semblance of a shape and started desperately stacking necklaces when she realized this wasn't enough to save it. She also should have swiped Mahomes' pointy-toed booties, as her chunky platform heels were clearly the wrong choice.

Swift's hairstyle was not a hit on Reddit, either, with one critic observing that it was giving convent, not cool gothic poet. In short, what could have been a fun nod to "The Tortured Poets Department" just fell flat — a little black dress should look effortless and chic, not tortured.

Fans got to see what would happen if Taylor Swift's "Folklore" and "Reputation" eras collided when she enjoyed one of her earliest public outings with Travis Kelce, and the result was a flashback to the late '90s and early aughts. Maybe the florals on her sheer top felt romantic to Swift, but they bring to mind a design on cheap dinnerware that's desperately trying to look fancy. And what's up with those random blocks of garish green? It's like the designer ran out of print but decided that the shirt needed a little more color — and chose the worst possible hue.

A leather skirt and heeled combat boots completed Swift's alt-girl-lite look. But back to the top, which looked like something you might find on a discount rack at one of the mall stores where aughts-era teens on a budget used to shop. The shirt had some social media users begging Swift to get a stylist and others comparing her to various TV characters, including quirky "Smelly Cat" singer Phoebe from "Friends," teen trendsetter Lizzie McGuire from her titular Disney Channel show, and immature mom Lorelai Gilmore from "Gilmore Girls." But to say something positive about it, at least it wasn't Kelce's matching corduroy set.

People have joked about Taylor Swift's inability to slay. But you have to applaud her tenacity, as she obviously tries her best to serve. Unfortunately, Swift sometimes wears outfits that are inappropriate for the occasions she chooses them for. Many armchair fashion police felt this was the case when they saw her cheering for Travis Kelce during the Kansas City Chiefs' October 2024 showdown against the New Orleans Saints.

While many viewers at home were snuggled up in their flannel throw blankets, Swift was wearing hers. Well, not really, but her Vivienne Westwood corset top and skirt set did look like tartan coverlet origami. Her ensemble also included a pair of knee-high boots with platform heels from the same designer. On Reddit, some commenters complained that her outfit looked out of place at a football game. She was also accused of trying to hog the spotlight on her boyfriend's home turf. The smattering of glitter freckles she placed on her face certainly didn't help Swift make her case against these allegations.

By the time she wore it to the game, Swift had already made it abundantly clear that she was absolutely mad for plaid — she'd been wearing so much of it that fans were starting to wonder if there was some underlying meaning behind the pattern's frequent appearance in her wardrobe. It was also starting to feel a bit stale. If she was going to stick in a style lane, Swift should have asked NFL WAG designer Kristin Juszczyk to create some new game-day-appropriate pieces for her instead.

Black and white is a classic color combo, but it's not a foolproof pairing. Taylor Swift knows this all too well after wearing a white Schiaparelli gown and black opera gloves to the 2024 Grammy Awards. Her outfit garnered comparisons to one previously worn by Kate Middleton, so the singer gets a few points docked from her style scorecard for a lack of originality. Plus, any voluminous white dress with draping runs the risk of resembling a bedsheet, which was the case with Swift's gown. The sheer amount of fabric overwhelmed her, and as Katy Perry once said about Meghan Markle in an ET interview, "I would have done one more fitting."

Swift's hair was shoved over one shoulder and had an undone quality that was giving disheveled bride. Her excessive use of accessories almost served as a distraction from her locks, and she just couldn't resist prominently displaying a potential Easter egg among the stacked necklaces cluttering her clavicles and throat. She loves forcing her fans to become apparel analysts, so it didn't escape Swifties' notice that the time on her choker watch was frozen at midnight — was it just a nod to her record "Midnights," or something more? (It turned out to be the hour she would drop "The Tortured Poets Department" weeks later.)

The internet was quick to call out Swift for her dodgy styling. To top it all off, she somehow managed to make her outfit both boring and fussy.

When Miss Americana decided to add a new dress to her Eras Tour rotation in October 2024, the frilly frock sparked a great debate over what it most closely resembled. Fans who attended Taylor Swift's first show during the New Orleans leg of the tour got to witness the debut of the high-low dress, which is — let's be honest here — not an easy silhouette to pull off. Its mullet-like design makes it seem as though the wearer was too indecisive when trying to choose between looking glamorous in a gown or fun and flirty in a mini dress. The wildly imbalanced proportions of Swift's take on the style did nothing to improve it — the front was super short and there was too much volume in the back. However, it was the ombré color scheme of Swift's garment that captured her fans' attention.

Some Swifties thought the dress was meant to be patriotic and that it looked like one of those red, white, and blue popsicles. But don't expect Swift to change the lyrics of "Clean" to "You're still all over me like a flavored-ice-stained dress" — other fans observed that the top half of the garment looked more orange than red. Some members of this faction were on Team Tide Pod and others were on Team Koi Fish. The latter is a more apt comparison, as koi fish can be a blend of blue, orange, and white; Swift's ruffled skirt slightly resembled a fish tail; and she has a guitar with koi fish painted on it.

Taylor Swift has come far since her "Tim McGraw" days, but she still has a tendency to get stuck in a style rut — just like that former boyfriend of hers and his Chevy truck. Long after she put her "old faded blue jeans" in the rearview mirror, she updated her denim in a major way by rocking a cropped Versace bustier to one of Travis Kelce's games in September 2024. Its color was almost an exact match with the Grlfrnd jean shorts she paired it with. For a loud contrast, she completed her outfit with thigh-high Giuseppe Zanotti boots that were a bold red hue but not quite bright enough to match her boyfriend's team colors. One popular criticism on Reddit was that Swift looked "styled by Blake Lively," whose own outfits often miss the mark.

If Swift's corset looks familiar, it's because she wore an EB Denim "Polka" mini dress with a similar corset-style top to an MTV VMAs afterparty in 2023. She also had on the same Versace corset top in black when she and Kelce attended a "Saturday Night Live" afterparty together.

Swift's denim-on-denim ensemble and boots cost her a little over $3,000, while her Louis Vuitton purse and gold jewelry increased the value of her entire look to over $70,000. This price tag feels a bit excessive for a football game, but if Swift insists on splashing that kind of cash on a game-day outfit, she could at least put together something a little more exciting and original that looks like it's worth what she paid for it.