Art historians and artists often attempt to assign a unified code of meaning to colors used in paintings, regardless of the historical context and period norms surrounding them. In the fifteenth century, this primarily meant judging colors based on the cost of paint and their religious significance. For instance, gold represented nobility, and its expense added an air of dignity to artistic works. Some painters of the time challenged these regulations, believing that the meaning of a color varies based on the viewer or, more simply, that sometimes other colors just look better – even if they cost less to produce.

In his Painting and Experience in Fifteenth Century Italy, Michael Baxandall also disputes this color hierarchy and asserts that artists select their paints based on what they believe will best convey their ideas and communicate with audiences. In times of social or personal strife, painters attempt to reflect their emotions in new ways, and, in his later years, Henri Matisse used color to express the pain of war and his hopes for a better future.

Although Matisse painted Woman with a Hat technically before his Fauvist period. Fauvists used bright, violent colors to create pieces with more passion than ever before. Matisse introduced this movement during a particularly difficult period in his life when he had fallen ill, Nazis held his homeland, and his wife and daughter participated in the Resistance. He revealed his concern in his works of this period and experimented with various artistic styles. Despite his distress and the departure of fellow artists, Matisse refused to leave his country and, in so doing, diminish the value of French art. He instead utilized paintings to convey political meaning as a form of reserved protest. He asserted, "If all the talented people left France, the country would be much poorer. I began an artist's life very poor, and I am not afraid to be poor again… Art has its value; it is a search after truth and truth is all that counts."

Matisse’s brushstrokes in Woman with a Hat display his Neo-Impressionist style, and his subject wears melancholy in her expression. This work showcases Matisse’s imagination and his courage to rebel, even if simply from expectations of color use.