This paper relates the style of 16th century Flemish paintings by Goossen van der Weyden (GvdW) to the style of preliminary sketches or underpaintings made prior to executing the painting. Van der Weyden made underpaintings in markedly different styles for reasons as yet not understood by art historians. The analysis presented here starts from a classification of the underpaintings into four distinct styles by experts in art history. Analysis of the painted surfaces by a combination of wavelet analysis, hidden Markov trees and boosting algorithms can distinguish the four underpainting styles with greater than 90% cross-validation accuracy. On a subsequent blind test this classifier provided insight into the hypothesis by art historians that different patches of the finished painting were executed by different hands.