Taylor Swift is often celebrated for her impeccable fashion sense, gracing red carpets with elegance and style. However, even the most stylish icons have their off days. Swift has surprised fans and critics alike with a few outfits that missed the mark. From clashing patterns to questionable silhouettes, some looks have sparked discussion for all the wrong reasons.
This list explores seven times Taylor’s fashion choices left us puzzled, proving that even the most polished stars can have a fashion faux pas. Let’s delve into these moments where Swift’s style didn’t quite hit the high notes, offering a different perspective on her wardrobe choices.
1. The Sparkly Pantsuit That Felt Too Casual

At the 2015 MTV Video Music Awards, Taylor Swift dared to stray from her usual glamorous style with a bold choice that left fans divided. Opting for an Ashish sequined houndstooth two-piece, the ensemble featured a cropped top paired with jogger-style pants in metallic hues. Though the outfit shimmered, it felt overly relaxed for the grandeur of the event.
The sweatsuit silhouette, combined with metallic Louboutin heels, clashed with the night’s high-fashion expectations. Many felt that this casual approach missed the high-energy glamour typically seen at the VMAs, making it a surprisingly underwhelming choice for Swift.
2. The Denim Disaster

In 2023, Taylor Swift revisited early-2000s fashion with a denim corset mini-dress at the VMAs after-party. Designed by EB Denim, the dress featured a playful pleated skirt paired with platform sandals. While nostalgic, the look veered more towards casual than chic.
Her half-up hair and layered necklaces added to the informal vibe, drawing comparisons to a “2007 Billy Ray Cyrus” look. Fans and critics alike felt the ensemble was a rare miss, especially considering the event’s glamorous NYC backdrop, highlighting a year otherwise filled with strong fashion choices.
3. The “Eclectic Grandpa” Outfit

Embracing the “eclectic grandpa” trend, Taylor Swift stepped out in New York wearing an ensemble that sparked conversation. The outfit featured brown wide-leg trousers, chunky loafers, and a vintage GANT sweater. Although trendy in theory, the mix appeared mismatched and lacked the charm others achieved.
Social media humorously attributed this fashion choice to the “boyfriend effect.” Despite its cozy appeal, the style did not translate well for Swift, leading to a look that many saw as frumpy instead of fashionable. It was a rare misstep in her street style lineup.
4. The Wrinkled Purple Dress

Making one of her early red carpet appearances at the 2008 Young Hollywood Awards, Taylor Swift chose a creased purple cocktail dress. The choice was a surprising deviation from her typically polished image.
Wrinkled fabric combined with a heavy smoky eye created a disheveled appearance that missed the relaxed elegance she might have intended. Despite her youthful grace, this early attempt at a laid-back style fell short, leaving an impression of a look that needed a bit more refinement. It remains among her more forgettable red carpet choices.
5. The Post-Quarantine Floral Dress

At the 2021 Grammy Awards, Taylor Swift stepped out in a bold floral dress by Oscar de la Renta. The dress, while ambitious, overwhelmed her petite frame with its abundance of colorful blooms. It seemed to swallow her whole rather than accentuate her elegance.
The sheer volume of the pattern made for a chaotic visual experience, drawing attention away from Swift herself. The vibrant floral design clashed with the red carpet, creating an unintentionally jarring effect.
Despite its artistic intent, the ensemble missed the mark, leaving critics questioning the choice for such a prestigious event.
6. The Poofy Lace Wedding Look

During the 2013 Brit Awards, Taylor Swift appeared in a lacey white gown that evoked bridal imagery. The puffed silhouette and lace details seemed more fit for a wedding aisle than a bold performance.
Fortunately, Swift turned the moment around by dramatically tearing away the dress mid-performance, revealing a sleek black lace bodysuit with leather pants. This transformation salvaged the fashion moment, showing Swift’s flair for theatricality. While the initial look didn’t quite resonate, her ability to pivot onstage showcased her showmanship and creativity.
7. The Gold Fringed Dress Overload

At the 2020 Golden Globes, Taylor Swift donned a striking blue-and-yellow floral gown by Etro. The dress featured voluminous shapes and massive cutouts, dividing critics and fans. While known for embracing bold colors, the gown’s overwhelming design felt more like costume than couture.
Critics argued that it overshadowed her frame, creating an effect that bordered on chaotic. The look landed on several “worst-dressed” lists, marking a rare fashion misstep for Swift. This instance highlights the fine line between daring and overdone in the world of high fashion.
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