Taylor Swift knows how to rock a fashion trend. 

From strange color choices on the red carpet to awkward TikTok attempts, here are rare moments when Swift looked less than perfect. 

Taylor Swift’s 2015 VMA pantsuit was not elegant.

In the “1989” era, Taylor Swift’s looks were glitzy and shiny. This was shown at the 2015 MTV Music Video Awards. The public was used to seeing Swift in long, elegant gowns for the occasion. For this event, she wore a glittering houndstooth two-piece set by Ashish. The top was cropped at the ribcage, and the pants were like joggers. 

Fans blamed Swift’s stylist, Joseph Cassell Falconer, for the fashion fail.

 

The 2024 Grammys look was costume party glam.

High glam doesn’t guarantee elegance. Swift has a history of looking great at the Grammys in long dresses. But at the 2024 event, she took a different approach. That year, Swift wore a white Schiaparelli gown with a cinched waist and a thigh-high slit. Swift paired the ensemble with long black gloves, heels, and necklaces. She looked like she stepped out of a black-and-white film, but it looked more like she came straight from a costume party.

Her 2023 VMA afterparty outfit would have played better at a summertime barbecue.

Taylor Swift wore all denim, and the denim-on-denim trend is everywhere. At the 2023 VMAs, her outfit made her look like she was going to a barbecue. Swift wore a denim playsuit by EB Denim with a pleated skirt and tank top. She paired the look with silver sandals and necklaces.

It didn’t fit for fans. The shoes and denim were nice, but the whole look was too busy, and Swift’s hair was too heavy.

The black shorts looked cheap.

In May 2023, the singer was seen leaving a studio wearing black shorts, tan sandals, and a white blouse. The loose top made her look squat. The crisscross black shorts cost nearly $400 and were a big no-no for fans.

Her “Eclectic Grandpa” look was a flop. The trend may be popular on TikTok, but it’s only for some. Taylor Swift’s look proved some aesthetics are only for some. She wore brown loafers with brown trousers and an orange sweater by GANT. The brown tones were confusing, and the grayish brown trousers made it look more like a 1990s librarian than an off-duty pop star. Swift’s light spring complexion looked washed out against the earth tones.

 

Swift’s outfit needed to be updated.

In 2020, Taylor Swift won Best Solo Act at the NME Awards in London. Swift wore a two-piece suit made of pinstripe shorts and a matching blazer with an off-the-shoulder blouse. The lace-up white booties seemed outdated, which was surprising for a star on top of the trends. The slouchy shoulders and boots made the outfit look sloppy and short. One person wrote on Reddit that Swift needs a better sense of style and a new stylist.