Taylor Swift's Worst Outfits From Every Era

Swifties know that every new Taylor Swift album is more than just an album — it's the dawn of a new era. With a whopping 14 albums under her belt, Swift has been giving fans new eras since she hit the music scene with her debut album when she was just 16 years old. Swift has spent more than half her life in the spotlight, so it's no wonder she has gone through so many eras in the public eye. And, just as every era had its vibe, its songs, and its iconic moments, every era also had plenty of outfits. Some have stood the test of time, and others were memorable for all the wrong reasons.

For someone who has sported as many ensembles in front of a worldwide audience as Swift has over the years, she has had fewer outfit flops than we may have expected. Still, throughout her many eras, she has had a bad outfit or two from each one. From her "Fearless" ensemble that just screamed "2009" to the confusing look that started "The Tortured Poets Department" era, every era has its ultimate fashion flop, and we've got them all. As it turns out, while Swift may "never go out of style," some of her looks sure have.

Taylor Swift was just 16 years old when her self-titled debut album was released in 2006. This is why it comes as a surprise that her worst look from her "debut" era earned its title due to how much it aged her. She sported this black sequin dress to the 2007 BMI Country Awards, but there's really nothing wrong with the dress itself. The dress is a bit too long for opaque black tights, and the updo and earrings just don't quite work with what should have looked like a young, fun dress. 

Taylor Swift had many big moments during her "Fearless" era, which began in 2008. She transitioned from her country roots to the pop world, and Kanye West infamously interrupted her at the Grammys. She also wore some beautiful red carpet looks and adorable, on-trend streetwear. Not every outfit can be a hit, though. The worst one? This look that she sported in 2009 that was just so 2009. The leggings, the sparkly flats, the big belt over the shirt? It was a sign of the times, as well as a total flop.

In 2010, Taylor Swift hit the Roberto Cavalli show during Milan Fashion Week. Swift's look for the occasion wasn't horrible, but it could have been a lot better — especially for an event all about fashion. Her hair and makeup were stunning and coordinated perfectly with the romance of her frilly top. However, the bottom half of the outfit was a major detail overload. The boots, tights, and skirt all felt like statement pieces on their own and needed to be balanced better with pieces with fewer special details. 

Taylor Swift graced many red carpets during her "Speak Now" era, which kicked off in 2010. On these red carpets, she mostly looked like the epitome of up and coming superstar. Unfortunately, at the 2011 Met Gala, which was "Alexander McQueen: Savage Beauty"-themed, her look just didn't work. The asymmetrical top of her J. Mendel gown was beautiful and elegant, but the bottom felt mismatched with the rest of her look. Furthermore, to complement the edginess of the detailed hem on the dress, sleeker and more modern hair and makeup would have looked better.

The year 2012 kicked off the iconic "Red" era, as well as a distinct transformation in Taylor Swift's style. She loved a black, white, and red color palette and vintage menswear-inspired pieces, like loafers, suspenders, and hats. At the time, this vibe often felt cool and fashion-forward, but not every outfit stuck the landing. On The RED Tour in May 2013, she wore skin-tight leather shorts with a tucked-in lace top, a fedora, and a pair of loafers. Perhaps any one of these pieces would have worked with a different look, but they totally clashed together. 

Taylor Swift attended the 2013 CMT Music Awards in a beige Elie Saab dress. An all-beige look can often look "blah," and this is particularly true for Swift since this color just blends into her own coloring and doesn't make her pop. As is often true with Swift, the way she styled this dress didn't help, either. The complicated strappy shoes clashed with the flowy, breezy dress, and her hair may have been better down and undone to lean into the effortless vibes of the dress.

Few of Taylor Swift's looks over the years had us quite as perplexed as the dress she wore while performing at the 2013 Brit Awards. Swift looked stunning in a sleek, black Elie Saab number on the red carpet, but when she took the stage to perform "I Knew You Were Trouble," she wore a confusing wedding gown with a strange geometric silhouette. She ditched the gown for short shorts and a top she had underneath it, but the quick change didn't make the vision behind her gown any clearer. 

The 1989 era could be renamed "the era of shorts," as this was Taylor Swift's preferred article of clothing during this time. Hey, with long legs like hers, we get it. That said, sometimes Swift nailed her shorts-centric looks, and sometimes she didn't. At a Tommy Hilfiger show in 2016 Swift sported this strange shorts and top ensemble with red velvet over-the-knee boots. The boots are definitely what made this look a flop, but overall, we just don't see the vision.

Taylor Swift's 2016 Met Gala look made her look like an entirely different person. Overall, her platinum blonde bob just wasn't her best hair moment — the color simply didn't complement her features. Also, her overly complicated seemingly Tin Man-inspired ensemble made it even worse. We love it when a Met Gala look fits the theme, and this outfit did work with "Manus x Machina: Fashion in an Age of Technology." However, it still just looks messy and odd. 

When "1989" arrived in 2012, this era brought about Taylor Swift's first entirely pop album as well as many, many crop tops. While quite a few of these crop top looks were hits, her 2015 Video Music Awards matching set just wasn't her best. This set has so much going on: the sportswear-inspired silhouette, the metallic ombre colors, the houndstooth, and the sequins. These elements just didn't jive together and left Swift with a look that didn't make a clear statement. 

The "Reputation" era has quite a reputation, revolving around edginess, revenge, and of course, snakes. While Swift swapped snakeskin out for leopard print while out and about in Tribeca in 2018, her 'fit still fit the era perfectly. Despite being unquestionably "Reputation"-coded, though, this look also clashed. The studded heels, leopard print miniskirt, and lacy shirt layered over a bralette all felt tacky on their own, but pairing them together felt like a clubwear overload. 

We all loved Taylor Swift's "Lover" era, but we didn't love every outfit it brought about. The navy jumpsuit she wore to the 2019 Billboard Women in Music event was one not-so-lovable "Lover" look. It was refreshing to see Swift in a wide-legged pant since she shows off her gams in most outfits. However, while we like the idea of this jumpsuit, something about its fit was all wrong. It felt overly baggy, and both the neckline and the pants' hemline were a bit off. Plus, the dangling waist chain added to the look's messy vibe.

At the 2019 iHeart Radio Music Awards, Taylor Swift sported an extremely short sequin romper. The "Lover" era was all about playful, flirty looks, and of course, wearing an outfit entirely of sequins fits this vibe to a tee. Still, this romper just didn't feel right for a red carpet. While there's nothing wrong with short shorts, these just felt a tad too short, and the cut of the top threw the silhouette off-balance. Furthermore, the shoes and lack of other accessories didn't add anything to the look. 

During the Eras Tour, Taylor Swift has certainly proven that she's capable of a quick change. So, why didn't she change out of her performance look when it came time to accept awards at the 2019 American Music Awards? While the outfit may have perfectly encapsulated the "Lover" era with its pink hue, glitter, and theatrical vibe, it just seemed odd for giving acceptance speeches. Even something as simple as ditching the cape and layering on a skirt could have transitioned the look into a great award show ensemble. 

Of course, 2020 was quite an eventful year for all of us, and Taylor Swift was no exception to this. The year gave Swifties the "Folklore" and "Evermore" albums, and Swift showed off her folksier singer/songwriter chops. While not every outfit Swift sports during one of her eras has to fit the vibe of the album, her 2020 NME Awards look couldn't have clashed much more with the "Folklore"/"Evermore" era. The off-the-shoulder pinstripe set was peculiar and busy enough on its own, but the white boots and bag just added more elements to an already all-over-the-place ensemble. 

At the Academy of Country Music Awards in 2020, Taylor Swift hit the Grand Ole Opry stage in pared-down makeup, undone hair, and a pair of khaki pants. Sure, she dressed the look up a bit with a sequin top and strappy sandals. However, all of these elements together felt incongruous, and the look was just overall a bit "blah" for a performance look. The easy breezy hair and makeup felt perfect for the "Folklore" and "Evermore" eras, but it would have been complemented better by a flowy top or long, ruffled dress. 

Taylor Swift's "Midnights" took the world by storm in 2022, and it's a particularly important era since it kicked off the Eras Tour, which began in March 2023. The "Midnights" era also kicked off a series of less-than-stellar red carpet looks, including, but not limited to this gold jumpsuit from the 2022 American Music Awards. This jumpsuit just didn't look like it was good quality or like it fit her properly, wrinkling and bunching in odd places. Furthermore, the color washed her out, making her hair, skin, and ensemble all look monochromatic. 

Taylor Swift certainly fit the "Midnights" era vibe when she wore this Roberto Cavalli two-piece set to the 2023 Grammy Awards. This set definitely wasn't her worst look ever, but a few elements kept it from working. For starters, the section of bare midriff just felt a bit too big, and it clashed with the otherwise elegant look. This set would have stunned as a dress with no cutout and no sleeves. Furthermore, the hair and earrings just seemed to clash with the rest of the look.

Two Grammys looks in a row? Say it ain't so! Unfortunately, the look that kicked off "The Tortured Poets Department" era was far worse than Taylor Swift's 2023 Grammys look. Swift announced the beginning of a new era at the 2024 Grammy Awards. Fans didn't yet know what "The Tortured Poets Department" would have in store or that this ensemble fit the black-and-white theme of the era to come. Unfortunately, the hair and accessories just made this look fall flat, and it's definitely not something to write poetry about. 

Since she started dating Travis Kelce, Taylor Swift has perfected the art of game-day looks. Just as the Kansas City Chiefs win some games and lose others, their most famous cheerleader's ensembles can be either hits or misses. In October 2024, Swift sported platform boots and a plaid minidress to the Chiefs game. This outfit's biggest issue is that it doesn't fit the occasion. With brown tights and brown booties, this dress could have been cute for an autumnal day out, but something a bit more effortless would work better for Monday Night Football.