This study investigates the conventions of icon painting based on two icons representing the same motive. Hodegetria by Berlinghiero Berlinghieri painted in the 1230s and The Theotokos of the Don by Christabel Helena Anderson painted 2011 both present the motive of hodegetria. These two icons are analysed using Panofskys analysis model before they get compared to each other and against the conventions of icon painting. This is done in hope to obtain if icon paintings theoretical rules are being followed in practise. This study had shown that the conventions of icon painting have been changing through the years ever since 120 A.D. and so have the icons. The differences are often small and may not be visible to the naked eye.