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 6 of 9 ADVERTISEMENT () Start Slideshow Share This Link Copy ← Use Arrow Keys → 6 2015 Grammy nominations: 3 Record of the year, "Shake It Off" Song of the year, "Shake It Off" Best pop solo performance, "Shake It Off" How many she won: 0 Previous Next Start Slideshow Award SeasonGrammy AwardsTaylor SwiftMusic