Jack

For Jack's look, we believe she has had more time to explore her gender and makeup and so she would probably wear something low-maintenance but still bold and expressive. For example, a light smoky eye that can be reapplied upon waking up without having washed your face. Her smudged eyeliner has an androgynous edge. Jack may also experiment with brow shapes.

It doesn't seem like Jack would necessarily worry about being too "feminine" or too "masculine" like Maura does throughout the show. Jack is much more secure in her identity and in herself so she also wouldn't worry too much about her eyeliner being "perfect", she likes it messy.

Maura

Maura's gender expression is way more gray area. She is still experimenting with things such as makeup and clothes. At the beginning of the show, Maura is not someone who wears makeup. She has had a very natural look her whole life and then we see her experiment with makeup in the show. Because she hasn't done it before, her makeup look in scene 8 should be amateur hour. That is, she is brand new at makeup and so probably cannot apply it correctly. So, keep the stage makeup simple and light! Mascara is a yes! In scene 8, we recommend a pink sparkly eyeshadow over her eyelids and maybe darkened eye brows.