This painting is one of a series of seven watercolours entitled ‘Nightshift,’ in which the artist explores a private world that contrasts with the typical male persona. The title suggests the shift of character and appearance that takes place at night. The works show men dressed as women, influenced by Peter Ackroyd’s book on transvestism and dressing up, and by British comedians of the 1960s and 1970s, who dressed as women as part of their acts. The men depicted in these works are not drawn from life but are characters. Holding a small bag, this awkward-looking man appears simultaneously comic and unsettling. In these paintings, Flannigan suggests that there is artifice involved in all types of beauty.