In the early days of PostScript fonts, I designed a font of leaves called XLeafMeAlone. In 2006 I decided to revisit this topic and the result was two sets of new leaf fonts: MapleOaks and MoreLeaves.
MapleOaks contains almost 100 images of maple, oak, and sycamore leaves, and MoreLeaves has almost 100 images of leaves of various other species. There are four MapleOak fonts. They have identical images; only the orientation of the images is different. In MapleOaksUR the tips of the leaves point to the upper right, in MapleOaksDR the tips point down to the right, etc.