Inappropriate Outfits Taylor Swift Has Been Caught Wearing

Taylor Swift is no stranger to controversy (she'll be the first one to tell you about them in her songs!). But unfortunately, that goes for her fashion choices, too. 

As Swift underwent a serious transformation over the years from an innocent, starry-eyed country crooner to a pop megastar, her look inevitably changed as well. Long ago were the days when we could rely on her to show up to an awards ceremony in a prom dress and cowboy boots. "I play the tape of my life forward and don't wear the things that my kids or grandkids will make fun of me for wearing, [like] 'Wow, cool, Mom, cool cowboy boots that you were wearing constantly in 2006!'" she (perhaps famously) joked to Glamour in 2014. 

Alas, that certainly was ages ago in the pop culture discourse, and while we love how far Swift has come and how each album essentially comes with its own era (fashion included), there were bound to be a few missteps along the way. And there has simply been no hiding from the ridicule and backlash that has Swiftly ensued in some cases. It's nothing the headstrong pop queen can't handle, but keep reading to learn about Swift's most inappropriate outfits she's been caught wearing!

Did Taylor Swift get dressed in the dark?

Have you ever woken up late and scrambled to get dressed only to realize much, much later that maybe your shirt was inside out, your pants were unzipped or your shirt was on backward? Well if so, then you're in pretty good company. 

We hate to say it, but, as reported by Buzzfeed, Taylor Swift was guilty of committing that sort of fashion faux pas in 2014. As the story goes, Swift was spotted at a Knicks game with Justin Long sporting what appeared to be a red mock neck sweater. There's only one problem: she had it on backward. A Tumblr account opted to subtly let the masses know that the star might have made a teeny tiny mistake. "Taylor wears a 525 America sweater while leaving her apartment last night — en route to a Knicks game! Her Bordeaux sweater here is actually a reversible piece with Taylor opting to wear the neck cut outside for the front and the high-neck turtleneck to the back," the post read. In other words, the neck cut-out was supposed to be the other way. You get it.

Immediately, Swift caught wind of her error and took to Tumblr (very 2014) in a since-deleted post (via Insider) to confess to her transgression. "I think what they're trying to say politely is... I wore the shirt wrong didn't I?" Stars — they really are just like us!

Taylor Swift raised eyebrows at the 2016 Grammys

Remember when Taylor Swift raised some serious eyebrows at the 2016 Grammy Awards? The general consensus was that Swift committed a fashion no-no on the red carpet whilst pairing a coral pink tube top with a long satin fuchsia skirt (orange mixed with pink!?). To round out the look, the skirt included a daring slit all the way up to her inner thigh. Perhaps this was a case of color blocking gone completely wrong? 

Billboard likened the two-piece fashion miss to the infamous "10 Things I Hate About You" prom dress, while one Twitter user compared her outfit to that of a Flutterbye Flying Fairy toy. Yikes. Alas, it appears her hairstyle — a very blunt bob — only made matters worse. Swift was immediately compared to the Vogue editor everyone loves to hate, Anna Wintour. "shoutout Anna Wintour for opening @TheGRAMMYs...killed it," Complex tweeted at the time.

It's okay, Tay Tay. Not every fashion "lewk" is going to be a hit! That's what all of your songs are for!

Taylor Swift's Folklore merch landed her in hot water

Perhaps one of Taylor Swift's most controversial fashion choices is one she wasn't necessarily caught wearing ... but one that she helped design. With the surprise release of her beloved album, "Folklore," the queen of marketing and merch also launched a line of goods including sweaters and hoodies with the words "the folklore album" emblazoned in the top corner.

As reported by Glamour, a Black entrepreneur named Amira Rasool came forward on Instagram revealing that the logo Taylor Swift's team used bore an uncanny similarity to that of her own brand, The Folklore. "This morning, it came to my attention that musician #TaylorSwift is selling merchandise to go along with her new album Folklore. She is currently selling merchandise with the words 'The Folklore' printed on them. Based on the similarities of the design, I believe the designer of the merch ripped off my company's logo," Rasool posted on her Instagram account on July 24, 2020. 

Fortunately Swift and her team's response was.... well... Swift (see what we did there, yet again?) and the issue was rectified. "Amira, I admire the work you're doing and I'm happy to make a contribution to your company and to support the Black in Fashion Council (launching on 8/3) with a donation," Swift wrote on Twitter.

Phew! All's well that ends well! And so the journey continues.