The present invention relates to the automated cutting of pliable items. More particularly, the present invention relates to the automatic cutting and/or trimming of pliable items, such as a shoe upper that lacks uniformity. An image of the pliable item is captured having image features and a pattern is retrieved having pattern features, such as a proposed cut path. An image feature is compared to distance tolerances associated with pattern features to adjust the proposed cut path such that it satisfies the distance tolerances while providing a consistently sized and shaped trimmed item.