Beautiful portraits, to paraphrase Jim Richardson, require beautiful subjects. But it is also important to have a degree of curiosity about the sitter, to discover angles and perspectives of interest. The movements of a large format camera allow some deviation from standard sharpness, perhaps enabling the finer elements of character to show through. This was shot using a softbox of two flashguns and a lens from around 1910.
Taking the subject into an environment that is wholly new for them can lead to some unexpected reactions, even if the immediate cause is just sunshine and a blustery wind. The light was good as you can see from the contrast of dark clouds in the background, and the air had the smell of summer. It is one way to try shooting an authentic portrait of a singer.