Our attraction to fossils is almost as old as humans themselves, and the way fossils are represented has changed and evolved with technology and with our knowledge of these organisms. Invertebrates were the first fossils to be represented in books and illustrated according to their original form. The first worldwide illustrations of paleoinvertebrates by recognized authors, such as Christophorus Encelius and Conrad Gessner, considered only their general shape. Over time, paleoillustrations became more accurate and showed the position of organisms when they were alive and as they had appeared when found. Encyclopedic works such as those of the Sowerbys or Joachim Barrande have left an important legacy on fossil invertebrates, summarizing the knowledge of their time. Currently, new discoveries, techniques, and comparison with extant specimens are changing the way in which the same organisms are shown in life position, with previously overlooked taxonomically important elements being displayed using modern techniques. This chapter will cover the history of illustrations, unpublished nineteenth-century author illustrations, examples showing fossil reconstructions, new techniques and their influence on taxonomical work with regard to illustration, and the evolution of paleoinvertebrate illustration.