It’s an honor just to be nominated, but winning at the Grammy Awards isn’t so bad either. Just ask Taylor Swift, she knows. Trophies are forever, but so are red-carpet photos, and looking back on what artists like Swift chose to wear over the years is something of a sartorial time capsule.
Swift, who attended her first Grammy Awards ceremony in 2008 as a 19-year-old nominee for best new artist (she was up against Ledisi, Feist, Paramore, and Amy Winehouse, who ultimately won the category), has won 14 Grammys total. She has been honored with the album-of-the-year award a record-setting four times, with her latest win in 2024, for the album Midnights, breaking the tie she’d previously held in the category with Frank Sinatra, Stevie Wonder, and Paul Simon.
Though Swift’s latest effort, The Life of a Showgirl, isn’t eligible for the awards this year due to its October release date, she may still be a guest at the ceremony. In celebration of the Grammys 2026, revisit Swift’s Grammys looks, from the ethereal pale purple strapless Sandy Spika gown she wore for her first time at the ceremony in 2008, to her 2025 choice of a sparkly red custom Vivienne Westwood look accessorized with a tiny “T” charm on a chain—perhaps a nod to fiancé Travis Kelce—codesigned with Lorraine Schwartz, coyly adorning her thigh.
Ahead, take a walk down memory lane and see all 12 dresses that Taylor Swift has worn to the Grammy Awards over the years.
-
Frazer Harrison/Getty Images
2008 Grammys
In Sandy Spika.
-
Dan MacMedan/WireImage
2009 Grammys
In KaufmanFranco.
