Popsugar Entertainment Award Season How Many Grammys Does Taylor Swift Have? Taylor Swift Won Her First Grammy When She Was Only 20, and That Was Just the Beginning 11 February 2019 by Kelsie Gibson View On One Page Photo 3 of 9 ADVERTISEMENT () Start Slideshow Share This Link Copy ← Use Arrow Keys → 3 2012 Grammy nominations: 3 Best country album, Speak Now Best country solo performance, "Mean" Best country song, "Mean" How many she won: 2; best country solo performance and best country song Previous Next Start Slideshow Award SeasonGrammy AwardsTaylor SwiftMusic