A couple things it is useful, but not necessary, to know about Aleah Chapin when approaching her work.
First is a biographical detail. I'm not clear on the whole story, but I have the impression she was raised around her mom and her mom's buddies, "the aunties," and that the aunties are willing to consider alternative relationships with wearing clothing. So the women in Chapin's paintings are the community in the midst of which she was raised. Her figures are people with whom she has a life-long relationship.
The second is a professional detail. Chapin attended the New York Academy of Art. This Warhol-cofounded school is, counterintuitively, one of the foremost centers of training in classical, representational painting in the United States. I didn't go there myself, but I paint figures and I live in New York, so I run into NYAA grads all the time.