Wildly Expensive Things You'll Find In Taylor Swift's Closet That Weren't Worth The Money

Taylor Swift has undergone a serious style transformation since skyrocketing to global pop superstar status. The iconic singer had originally gone out of her way to style pieces that her fans could afford and promoted attainable brands like Target; however, with her increasing wealth, the star's fashion relatability has fallen by the wayside. It seems Swift has opted for quiet luxury (and sometimes loud luxury) over sustainability and connection. In 2023, Swift became a billionaire, so it makes sense that her attempts to remain relatable have come up a little short.

There's no denying that the pop star truly has her own quirky personal style that often weaves in the aesthetics of her latest albums. This approach has made her a hit or miss fashion icon, with some looks that even Swift's killer legs couldn't save. The pop star has donned outfits that totally rocked the red carpet and others that left us hearing crickets from her swarms of fans. And, with some incredibly deep pockets, these misses from the "Cruel Summer" singer brought with them a huge price tag.

Between curtain calls and football games, Taylor Swift met with patients, staff, and families in the halls of Joe DiMaggio Children's Hospital in June 2025. The stop was a total surprise and a great success. Her outfit, on the other hand, was a total miss.

The muted olive Loewe dress, which flaunted a price tag of over $2,000, featured a keyhole cutout in the neckline with a shoelace tie that mirrored the dated and out-of-place tie belt. The wrinkly fabric gave the dress a cheap look, only made worse by the extra material of the belt that fell awkwardly short of the hem. 

Taylor Swift made a bold statement with this December 2024 look as she stepped into the tunnel of Arrowhead Stadium. Her red suede coat displayed a thick trim of fur around the collar, down the front, and circling the hem –- not to mention its huge puffy cuffs that hid her hands from view.

The dated '70s throwback screamed of fads from days past and looked tacky with Swift's poorly paired bucket hat. For a piece that was so obviously a no-no in fashion books, its $427 price tag begs the question: What was Swift thinking?

Given her many, many extravagant (and occasionally over the top) looks for previous Chiefs games, it was a little surprising to see the "All Too Well" singer step out in such a simple look for the 2024 Super Bowl. But don't be fooled, Taylor Swift's wardrobe always features flashes of her wealth.  

Swift's black jeans with two bizarre thigh slits bordered in crystals cost a whopping $695. The hefty price tag didn't change the fact that the jeans were ... boring. Their bedazzled cut-outs failed to be compelling and overall made the price a bad decision for the pop star. 

While in New York between her Eras Tour performances, Taylor Swift was photographed in a Vivienne Westwood mixed-patterned dress with a highly structured design. Some pieces have incredible execution and design but are such a statement that they end up overpowering the wearer. That is precisely what happened to Swift in this frock.

The dress almost looks like a paper doll outfit that has been gingerly added on top of the singer's figure instead of flowing with her natural lines. Though Swift's love for Westwood is no secret, she was unable to pull off the $2,390 piece.

Taylor Swift strutted through the tunnels of Arrowhead Stadium in a mini pleated skirt, maroon tights, black boots, and a Louis Vuitton slouchy jacket back in January 2025. Eyes were immediately drawn to the black and gold jacket that boasted a tacky print of Louis Vuitton's logo throughout the bottom half of the piece.

With its baggy design and hoodie styling, it looked like a knock-off designer piece that didn't suit Swift's pop star persona. However, the reality of this expensive piece was a totally tacky design with a price point of $5,000.

Attending the 2021 Grammy Awards ceremony, Taylor Swift walked the red carpet in an Oscar De La Renta floral mini dress with 3D elements. The mix of large and small flowers, overlapping petals, and loud colors made for a distracting and cringeworthy look for the pop queen.

Swift dropped $8,990 on this crazy busy dress that drowned the singer's figure in an atrocious pattern that was only made more complicated by the illusion panels tucked between the mammoth florals. Where the dress should have opted for subtlety, it instead added more chaos with its bell sleeves that hung well beyond the ends of Swift's fingertips.

This look from the 2022 VMAs had Taylor Swift literally dripping in jewels. While the piece was a masterful design and interesting dress, the imagery of Swift drenched in diamonds was not necessarily the look the star should have been striving for, given her enormous, growing wealth.

As a result, even though she was only a multi-millionaire in 2022, Swift was left looking tacky, tone-deaf, and like a bit of a braggart. In light of her billionaire title, this image of the pop star dripping in jewels and diamonds looked even more vain (especially when considering its almost $25,000 price tag).

Stepping on to the American Music Awards red carpet in November 2019, Taylor Swift donned a green sparkling dress that warranted more questions than applause. The dress lacked any structure, which would have done its draping effect some good, and sat unflatteringly along the singer's waist and shoulder. 

The drape from strap to waist was bizarrely placed and awkward, making it all look as though it was added last minute. Not to mention that the black spaghetti straps visible alongside the green looked like unintentional sightings of Swift's bra strap. It was just another downright distractingly bad look from Swift with a high cost. The dress was designed by Julien Macdonald whose gowns range in price from $10,000 and $40,000.