Even the biggest Swifties must admit something about their beloved queen: the woman is not known for high fashion.
While she tends to look fairly flawless rocking a sequin leotard on stage, when she’s out in the real world, she more often than not wears the type of clothing that make people question whether or not she has a mirror (or if she’s read a magazine since 2010). As much as Swift can deliver empowering song after empowering song, it appears she sometimes has no idea what decade she’s in when it comes to style.
In fact, Swift’s bad sense of style is so notorious that some in the industry have actually tried to explain it as just another strategy on Swift’s part. “She knows her audience, and everything she does is, in some way or another, catering to that audience, whether it’s purposeful or subconscious,” fashion correspondent Lauren Sherman tells Business Insider.
No matter how you slice it, strategic or not, Taylor Swift, despite all her awards, record sales, and massive Tortured Poets Department era, will never be remembered as someone who was at the forefront of fashion. But, hey, you can’t win ’em all. While there have easily been hundreds, if not thousands of times that Swift has been caught wearing outdated trends, sometimes you need to just pick a few of the most “Really?!” ones for the sake of time and space.
The see-through black lace look was so 2010s tumblr
By 2018, many of us were well aware that the music festival aesthetic of the 2010s was starting to become passe for street style. Swift, however, didn’t appear to get the memo, as one candid shot of her from that time showed her stepping out of a Manhattan building in a denim leopard miniskirt and black see-through top. The singer was apparently in her “reputation” era at the time, so it’s possible she was doing this to deliberately buck the trends. In any case, it was a surprising choice for streetwear, given how successful and current her “1989” era looks were.
The all-denim look is a y2k trend best left in the past
When it comes to an epic fashion faux pas, it’s really hard to not immediately think of Britney Spears and Justin Timberlake showing up to the 2001 American Music Awards in matching denim outfits. Even for the time — and the early 2000s was cruel when it came to fashion — it was deemed a total disaster.
In her memoir, “The Woman in Me,” Spears wrote about the head-to-toe denim look that will be forever burned into our memories. After finding out that Timberlake intended to wear jeans to the event, Spears wrote in her book, “and I said, ‘We should match! Let’s do denim on denim!’ I didn’t think my stylist would actually do it, and I never thought Justin would do it with me. But they both went all in.” Spears also called the look “tacky,” but admits she likes when it pops up as a Halloween costume.
But despite the fact that the look has been called “tacky” by the woman who actually wore it, that didn’t stop didn’t stop Swift. As we can see here, she wore a dress made of varying shades of denim pieces with a frayed hem to a party in September 2023.
The fitted floral long-sleeve tee and boots was giving dELiA*s catalogue
If when you saw the photo of Swift out with Travis Kelce in New York and immediately thought, “But I thought dELiA*s went out of business?” then you’re definitely not alone. You could pick up a dELiA*s catalogue from anytime during its initial launch in 1993 to when it folded sometime in the 2010s and easily find Swift’s outfit — from the fitted, floral green tee to the shiny, black work boots and the suspiciously small shoulder bag. Granted, her new beau doesn’t seem to be aware of what year it is either based on some of the outfits he’s been spotted in, so perhaps these two really are soulmates after all. Birds of a feather, as they say.
If when you saw the photo of Swift out with Travis Kelce in New York and immediately thought, “But I thought dELiA*s went out of business?” then you’re definitely not alone. You could pick up a dELiA*s catalogue from anytime during its initial launch in 1993 to when it folded sometime in the 2010s and easily find Swift’s outfit — from the fitted, floral green tee to the shiny, black work boots and the suspiciously small shoulder bag. Granted, her new beau doesn’t seem to be aware of what year it is either based on some of the outfits he’s been spotted in, so perhaps these two really are soulmates after all. Birds of a feather, as they say.
Her oversized blazer and floral slip made it look like she was out to lunch at Applebee’s in 1988
Let’s set the scene: It’s 1988 and you, despite living in Staten Island, work in Manhattan in the hopes of making your career-related dreams come true. When you see the opportunity to do that after your boss has a skiing accident, you begin to dress the part, to the best of your ability on your small salary. That look is all about power lunch blazers over dresses and, of course, a scrunchy in your hair. End scene.
Yes, that’s the plot of the iconic film “Working Girl,” but it’s also the best way to describe Swift’s outfit for Gigi Hadid’s birthday party in 2019. Featuring a baby blue dress and red, oversized blazer, the look was equal parts outdated and perplexing. The singer may have only lived in NYC for five years when this photo was taken, but even the newbies who just fall off the turnip truck know that this is an awful choice for a nighttime event in, based on the cobblestone, the West Village or Meatpacking District.
