Every Taylor Swift Grammys Dress, Ranked—Which One Was the Most Iconic?

From country princess to global pop powerhouse, Taylor Swift’s Grammys red carpet looks have evolved dramatically over the years.  

Whether she’s channeling classic elegance, bold fashion risks, or ethereal romance, her outfits always make a statement. But which one was the most iconic? Let’s rank them from forgettable to legendary

2021 – Cottagecore Dream Dressed in Oscar de la Renta’s floral masterpiece, Taylor embodied her folklore and evermore era, proving that romantic, whimsical fashion can still dominate the red carpet. 

2010 – Princess Moment Her deep blue KaufmanFranco gown, paired with cascading curls, was a perfect match for her first Album of the Year win (Fearless era). Classic, timeless, and magical. 

2013 – Too Much Bridal, Not Enough Wow Taylor’s white J. Mendel Grecian gown was elegant but lacked excitement—many thought it was more fitting for a wedding than the Grammys. 

2019 – Ruffles Gone Wild Taylor skipped the red carpet, but her ruffled pastel Stella McCartney gown at an after-party received mixed reviews—some fans loved the whimsy, others thought it was overwhelming. 

With The Eras Tour cementing her status as a style icon, fans are eager to see if she’ll embrace old Hollywood glam, modern edge, or a surprise throwback look at the 2025 Grammys. 

Support for the Arts: Through donations and advocacy, Swift has championed the arts and creative industries.  

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