Country pop artist Taylor Swift has achieved a lot of fame in a short time. She released her self-titled debut album in 2006 at just 16 years old. Her second album, Fearless, went on to be the best-selling album of 2009 and win four Grammys. Step 1 To start learning how to draw Taylor Swift, draw a large circle and then sketch her jaw line below it. Step 2 She is looking slightly to the side, so sketch a curved line through the circle that is positioned to the left. Draw a horizontal line through the middle of the circle. With these lines in place, sketch the outline of her facial features. Step 3 Carefully finish all of the details and then color her in, paying attention to shading. That is how to draw Taylor Swift.