Anna Rose Bain was born and raised in rural Wisconsin. She began drawing from the moment she could pick up a pencil. Inspired by her grandfather, who started painting at the age of 70, she spent her free time as a child sketching from nature and poring over art books.
Anna studied art at Hillsdale College in Hillsdale, MI, and graduated in 2007 with a Bachelor of Arts degree and departmental honors. She was the first in the school's history to have a solo senior art exhibit. She refined her education at the Florence Academy of Art in Italy, taking a figure painting class in the summer of 2006.