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It\u2019s an honor just to be nominated, but winning at the Grammy Awards<\/a> isn\u2019t so bad either. Just ask Taylor Swift<\/a>,<\/strong> 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.<\/p>\n 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,<\/strong> 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<\/a>, with her latest win in 2024, for the album Midnights,<\/em> breaking the tie she\u2019d previously held in the category with Frank Sinatra, Stevie Wonder<\/strong>, and Paul Simon.<\/strong><\/p>\n Though Swift\u2019s latest effort, The Life of a Showgirl<\/a>,<\/em> isn\u2019t 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\u2019s 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<\/a> look accessorized with a tiny \u201cT\u201d charm on a chain\u2014perhaps a nod to fianc\u00e9 Travis Kelce<\/strong><\/a>\u2014codesigned with Lorraine Schwartz<\/strong><\/a>,<\/strong> coyly adorning her thigh.<\/p>\n