The West Indies are a biodiversity hotspot. As such, many of the plant genera growing in this region remain poorly known from a taxonomic perspective. The tree genus Coccoloba, is one of these poorly known genera. One species in particular, Coccoloba diversifolia Jacq. is distributed throughout the Caribbean and varies in morphology, particularly leaf size and shape, in different parts of its range. Additionally, the taxonomic history of C. diversifolia is complex. The present circumscription of C. diversifolia dates to the middle of the 20th Century, and is an exercise in lumping. A number of narrowly distributed or endemic Caribbean taxa were synonymized to form the present widely distributed taxon. It remains unclear, however, if C. diversifolia constitutes a single, widespread biological entity, or rather a number of more narrowly distributed biological entities. To date, taxonomic circumscription has used only classical tools, such as verbal leaf description. I here apply more contemporary tools to objectively describe and compare leaf shape in C. diversifolia specimens from across its range in order to begin the process of disentangling what is likely a species complex. I extracted leaf images from digitized herbarium specimens and described them using Elliptical Fourier Analysis in MOMOCS. The leaf shapes were then compared using PCA and clustering methods. Additionally, in order to make a primitive assessment of the impact of environmental conditions on the leaf shape in C. diversifolia, I georeferenced the specimens using GeoLocate and extracted the values of the BioClim variables at each location. This preliminary work suggests that leaf shape in C. diversifolia is systematically different in different island groups. While the majority of specimens occupy a single cluster in morphospace (consistent with the current circumscription of C. diversifolia), the subsections of this cluster correspond to major geographic regions in the west indies (roughly consistent with previous circumscriptions). In this regard the Bahamas looks like the most well defined morphological group of plants. BioClim variables did not help to explain leaf shape, except in the Bahamas. Further work is planned to incorporate DNA, better curated material for leaf tracing, and the examination of other key morphological features in Coccoloba (ochrea).