The Most Inappropriate Outfits Worn By Taylor Swift

In each of Taylor Swift's musical eras, she has shed her previous aesthetic and reinvented herself, becoming something of a fashion chameleon. Over the years, she's gone from country girl to pop princess to indie queen — and most of the time, she nails each and every look. But now and then, Taylor Swift's clothes end up on a "worst outfits" list. In fact, a few of the pop star's looks have been downright inappropriate for the occasion. 

Just take the time when the singer wore a white dress to a friend's wedding. Way to steal thunder! Or what about the time when she wore a flowing maxi gown while clambering around on the Folklore cabin during the Eras Tour? Dangerous! Or there was the time when she chose a tiny crop top for her New Year's Eve performance in New York City. That must have been freezing!

Let's take a look back through some of Taylor Swift's most inappropriate outfit choices over the years.

Dressing appropriately means dressing for what you're planning on doing. For instance, it's appropriate to wear leggings and a sports bra to yoga class. It's also appropriate to wear a long gown to a gala. However, wearing a long, flowing dress while hanging out on a slanted roof? Not so appropriate. 

Swift made the mistake of choosing to wear an ethereal maxi dress during the Folklore section of her Eras Tour. While this would have been a great choice if she planned on keeping her two feet on the ground, the choreography saw Swift climbing up onto the roof of the Folklore cabin set piece. In 2024, the outfit choice nearly led to disaster when she appeared to trip on the skirt while descending from the roof (via X, formerly Twitter). Long gowns — not appropriate for walking on roofs. Noted.

There are a few cardinal rules when it comes to weddings: don't show up too early or too late, don't forget a gift, and never, ever wear white — or a color close to white — as it's usually reserved for the bride. However, in 2016, Swift broke this rule when she attended the wedding of one of her backup dancers, Eliotte Nicole.

Taylor Swift made headlines when she left Coachella on a private jet to attend Nicole's wedding for a short period of time before returning to Coachella again to catch the headline acts. While the gesture seems thoughtful, it raised eyebrows about the carbon footprint the pop star leaves on the planet due to excessive aviation travel. This came a few years before a heated debate about Taylor Swift's private jet tracking in 2024 and the exorbitant fuels emitted in order to be in many places at once. 

But despite the singer's swift attendance at the wedding and the unbridled air travel, she showed up in a bridal-esque colored dress. Many critics were quick to point out the off-white tone of this dress, pointing to the unspoken rule that wedding guests should opt for colors and styles that won't upstage or blend in with the newlyweds. It's safe to say that, though gorgeous, this particular frock wasn't exactly an appropriate choice on this occasion.

Crop tops are for summer and coats are for winter — that's something we can probably all agree on, right? Well, not Taylor Swift. In 2015, the pop star opted for a daring and not-so-weather-appropriate outfit while performing at Dick Clark's New Year's Rockin' Eve in New York City's Time Square. Many of us can attest that New York in December is inconceivably cold. However, Swift chose to wear a tiny crop top and a pair of fancy track pants for the performance, leaving her bare midriff exposed. She must have been freezing. 

As Bustle reported, some of her fans took to X, formerly Twitter, to express their shock at her strange outfit choice. "Tay does cold-weather attire so well, that it's a shame we didn't get to see some of her adorable winter wear," wrote journalist Sienna Fantozzi in response to the performance.

One thing Taylor Swift seems to love is wearing bridal-esque dresses to other people's weddings. The pop star attended the wedding of her long-time collaborator and friend, Jack Antonoff, and his partner, actor Margaret Qualley, in August 2023 — and, once again, she chose the most inappropriate dress for the ceremony. 

Outlets began reporting on the images of the star at the wedding and fans quickly noticed that she was wearing an off-white blue lacy dress that positively screamed bridal. Inevitably, a star like Swift was already stealing plenty of focus, and we're sure this bride-like dress didn't help.

Fans took to social media to express their disappointment with the look. "Who tf wears white to someone else's wedding?" one person wrote on Instagram. Another chimed in, "White to a wedding. Whyyyyy." A third commented, "What kind of wedding is this? Such inappropriate clothing." Honestly, we have to agree that this outfit choice wasn't exactly Swift's best style moment.

This is one Taylor Swift look that we can't exactly just shake off. In 2014, the singer released her music video for the single "Shake It Off" from her "1989" album. In one of the scenes, the singer danced in a variety of outfits and styles. One of those dance styles was, apparently, twerking. And for her outfit, the singer wore denim shorts, white sneakers, a leopard print hoodie, giant gold hoops, and a huge gold snake necklace — the uniform for twerking, we guess?

As one writer pointed out for the Daily Beast, this look could easily be interpreted as cultural appropriation. Swift looked, they noted, "like an off-brand Cheetah Girl" in this costume. "One white celebrity plus potentially harmful stereotypes plus the appropriation of black bodies as casual props equals some complicated math that no one in America is in the mood for this week," the writer summed up. Other people agreed. "Haven't watched the Taylor Swift video and I don't need to watch it to tell you that it's inherently offensive and ultimately harmful," tweeted rapper Earl Sweatshirt at the time. 

Taylor Swift tends to choose tour outfits that run the risk of revealing just a little too much to her audience like the time she walked across an air vent in a short, flowy dress and had a Marilyn Monroe moment during her "Speak Now" show in 2011.

During her Eras Tour in 2023, Swift opted for a daring one-legged catsuit during her "Reputation" set. The stunning sequined leotard was designed by Roberto Cavalli and featured a glittery red snake pattern. Though a totally stunning look, we have to admit that it might not have been the most appropriate outfit for performing on stage.

In fact, the singer has nearly flashed her fans on numerous occasions during the show — especially during one moment when the singer knelt down and leaned back, very nearly exposing — well — just about everything. The moment was captured and posted in a since-deleted video with one person commenting on X, "Well she trusts that suit a lot." Another tweeted, "I'm thinking her stockings must be thick and flesh colors to make it look like her skin so there is no way anything like that could happen. That's the only way I'd trust a suit like that lol."

What does one wear to a football game? Should you go for a sporty, casual look? A jersey repping your team? Or should you opt for your most expensive designer clothes? While you can technically wear whatever you want, most people tend to go with one of the first two options. However, in 2024, Taylor Swift rocked up to the Super Bowl to support her boyfriend, Travis Kelce, wearing a staggeringly expensive outfit — and some fans weren't too pleased.

The singer wore a mesh black tank top and a pair of black jeans with jewel-lined cutouts on the thighs. Although the outfit may have looked pretty basic, it turns out it cost a whole lot of money. As Page Six reported, her top was from Dion Lee and cost $720. Her jacket was by Erin Andrews and cost $130. Her Area jeans were $695. With all of her diamond jewelry, the look cost the singer over $60,000.

Fans weren't too pleased about it. "Not even a cute outfit and why would she wear this to a football game?" one user tweeted. They have a point — this is a pretty strange outfit for game day.

Fans of Taylor Swift probably know all about the famous "Folklore" cardigan. In her music video for the song "Cardigan," the singer wore a varsity-style white knit sweater with silver stars on the arms. She later sold the cardigan on her website and it became a key piece of Swiftie merchandise. 

However, the singer was soon accused of stealing the design from a Black-owned brand called The Folklore. Even the label on the cardigan looked eerily similar. "Initially I was so shocked," said Amira Rasool, the brand's founder to InStyle. "I'd heard of so many different Black women in particular who had been ripped off by large corporations by celebrities. And I just couldn't believe that it was happening to me." Swift later issued an apology and had the logo on her cardigan changed. It's safe to say wearing a stolen design is anything but appropriate. We're pleased Swift took action.