We illustrate the advantages of distance weighted discrimination for classification and feature extraction in a High Dimension Low Sample Size (HDLSS) situation. The HDLSS context is a gender classification problem of face images in which the dimension of the data is several orders of magnitude larger than the sample size. We compare distance weighted discrimination with Fisher’s linear discriminant, support vector machines, and principal component analysis by exploring their classification interpretation through insightful visuanimations and by examining the classifiers’ discriminant errors. This analysis enables us to make new contributions to the understanding of the drivers of human discrimination between males and females.