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Taylor Swift’s Most Unforgettable Fashion Missteps Amidst Her Romance with Travis Kelce

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Taylor Swift's Worst Outfit Fails Since Dating Travis Kelce

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Fans of Taylor Swift noticed a shift in her fashion choices after she began dating Travis Kelce in 2023, introducing a new avenue for her attire: game-day outfits. While she supported Kelce at Kansas City Chiefs games in stylish sweatshirts, she also promoted her album, “The Tortured Poets Department.” This contrast between casual sportswear and the ethereal themes of her music sometimes left onlookers puzzled.

One of her more notable looks was a simple red sweater she wore to the AFC Championship in 2024. Though it came from her friend Gigi Hadid’s brand, it felt underwhelming for such an occasion. Swift had previously advised fans to be bold yet stay true to their comfort zones with fashion. Thus, her choice could suggest she prioritized comfort over style amidst her evolving tastes.

The Colorful Fairytale Dress

Taylor Swift exiting a car in a multicolored Vivienne Westwood dress

In November 2024, Swift wore a whimsical Vivienne Westwood gown that evoked mixed feelings. The off-the-shoulder design and striking color palette made it a standout, yet the proportions of the knee-length skirt seemed awkward. Styled with a chunky gold necklace and lavish velvet sandals, the outfit lacked coherence and left critics questioning her fashion sense.

Some fans humorously connected the gown to a psychedelic fairy tale, reminiscent of a colorful clash between characters from classics. Ultimately, while attempting to add a fantastical flair, it landed on the list of her less successful outfits.

Channeling Holiday Cheer in Green

Blake Lively and Taylor Swift walking in NYC at night
 Robert Kamau/Getty Images

Swift’s foray into green began during her boyfriend’s football games and continued to the 2024 Golden Globes, where she wowed in a shimmering sequined gown. However, a subsequent green velvet dress in Brooklyn fell flat as she paired it with brown thigh-high boots, creating a disjointed festive look that drew criticism.

Swift’s attempt at a chic holiday vibe resulted in an unexpected resemblance to a Christmas tree, prompting mixed reviews from fans even among her generally supportive community.

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During the “Reputation” phase of her career, Taylor Swift sported snake-patterned boots, leading fans to assume she was hinting at the upcoming release of “Reputation (Taylor’s Version).” However, they were surprised when she released “The Tortured Poets Department” instead.

Taylor Swift’s accessories spoiled her little black dress

Taylor Swift walking in a little black dress and ankle boots
 Damebk/bauer-griffin

In January 2024, Taylor Swift enjoyed a fun night out with Brittany Mahomes and Cara Delevingne at Nobu, NYC. Mahomes donned a stylish gray houndstooth outfit inspired by Cher Horowitz, while Swift opted for an Alaïa dress that had a fair share of flaws. The dress, with its oversized top and loose sleeves, resembled a trash bag instead of flowing elegantly and didn’t flatter Swift’s figure. Although she tried to accessorize with gold jewelry to enhance her look, it only highlighted the shapelessness of her attire. A misstep in choosing chunky platform heels over more appropriate footwear further detracted from her look. Additionally, her hairstyle didn’t resonate well with online critics, making her intended gothic vibe fall short.

An outdated floral print plagued her ensemble

Taylor Swift wearing floral top and holding hands with Travis Kelce
 Gotham/Getty Images

During a recent public appearance with Travis Kelce, Swift’s outfit embraced a nostalgic late ’90s vibe, blending elements from her past music eras. While she may have viewed the floral design on her sheer top as stylish, it came off as reminiscent of low-quality dinnerware trying too hard to impress. The unexpected green blocks added an odd touch that failed to enhance the overall look.

Swift matched the top with a leather skirt and heeled combat boots, but social media users compared her outfit to budget finds from mall stores or characters like Phoebe from “Friends.” Despite the critiques, at least she avoided matching Kelce’s more questionable corduroy attire.

Her flannel choice didn’t help her fashion struggles

Taylor Swift wearing plaid Vivienne Westwood dress at Kansas City Chiefs game
 David Eulitt/Getty Images

While many chuckled at Taylor Swift’s fashion choices, her determination to impress remains commendable. Unfortunately, her outfit selected for a Kansas City Chiefs game with Travis Kelce raised eyebrows. While fans lounged in cozy flannel, Swift donned a Vivienne Westwood corset and skirt set that resembled an origami flannel blanket. Complaints about the suit being mismatched with the football environment surfaced, as did accusations that she sought the spotlight during Kelce’s game.

Despite Swift’s affection for plaid, her frequent choices began to feel repetitive, prompting speculation about whether it was a deliberate style statement or simply uninspired fashion selections. Collaborating with WAG designer Kristin Juszczyk for more fitting game-day looks might have been a better route.

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Her misjudged perspective on monochrome fashion

Taylor Swift wearing white dress, black gloves at 2024 Grammy Awards
 Jeff Kravitz/Getty Images

While black and white ensembles have a timeless elegance, they can lead to misses. Taylor Swift discovered this firsthand when she wore an elaborate white gown paired with black opera gloves at the 2024 Grammy Awards. Her choice was likened to an outfit previously donned by Kate Middleton, drawing some criticism for originality. The gown’s excessive draping gave it an unflattering bedsheet effect, leaving her looking overwhelmed. As Katy Perry once mentioned about Meghan Markle’s wedding dress, “one more fitting could have helped.”

Swift’s ensemble also featured her hair draped over one shoulder in a haphazard manner that resembled a messy bridal look. Her layering of accessories detracted from her hairstyle, including a choker watch with the time stopped at midnight – stirring curiosity among fans whether it was a playful reference to her album “Midnights,” or a hint for her upcoming work. The online community quickly weighed in, labeling her styling as both dull and overly complex.