Old lady with masks was painted at the height of James Ensor's so-called fantastic period, also known as his mask period. Originally, the artist executed the portrait on commission. After the painting was rejected, Ensor transformed it into an overflowing masquerade in which the short perspective and the accumulation of figures heighten the dramatic tension. The person portrayed is probably Neel Doff, the Dutch poet and publicist. The elderly lady's gentle appearance contrasts sharply with the grim masks and sinister skulls crowding around her. The aggressive, contrasting colour scheme of bright reds and greens emphasises the menacing nature of the mocking masks.