From long country curls to pink-dyed tips, Taylor Swift has experienced a major hair evolution throughout her celebrated career. While we've loved watching the pop star experiment with different styles and aesthetics during Swift's many iconic eras, not all of her looks can rank among the best. The "Shake It Off" hitmaker has sported some divisive haircuts over the years, but none have been as picked apart quite as much as the blunt bob she debuted at the 58th Annual Grammy Awards in 2016.