As consumers are becoming increasingly selective of what they wear on their feet, manufacturers are experiencing problems developing and fitting the right footwear. Literature suggests that shoes with a shape similar to feet may be comfortable because they attempt to maintain the feet in a neutral posture. The objective of this paper is to develop a metric to quantify mismatches between feet and lasts and also to be able to generate the two-dimensional outline of the foot using the minimum number of landmarks. Fifty Hong Kong Chinese were participants in the experiment. In addition to subject weight, height, foot length and foot width, the left foot outlines were drawn and 18 landmarks were marked on each of the two-dimensional foot outlines. A step-wise procedure was used to reduce the chosen 18 landmarks to eight, such that the mean absolute negative error (an indicator of 'tightness') between the foot outline and the modelled curve was 1.3 mm. These eight landmarks seem to show an improvement over those proposed by other researchers, thus showing the importance of choosing the right landmarks for modelling the foot. The positive and negative absolute errors were on average 1.8 mm and 1.3 mm respectively. Moreover, the mean errors for the toe region and for the rest of the foot were 1.7 mm and 1.6 mm respectively. The results indicate that the foot outline, an important component for footwear functionality and fitting, may be modelled using eight critical landmarks.