Portraying the Ineffable

German classical philosophy has sketched out the first doctrine of symbols which, however, very rarely becomes a subject of scrutiny. Its insights and findings are either missed at all or touched upon in passing. To fill in this gap and outline the German classical understanding of what a symbol is, where it comes from, and what task it performs is the aim of this paper. It is shown that Kant and his immediate followers Jacobi and Fichte paved the way to treating symbols as a sensuous vestment for thought; Schelling saw in symbols an embodiment of ideas tracing out the path to the due; Hegel imputed to the symbolic the function of primary language of creativity, while his disciples Vischer and Siebeck emphasized the role of personification as well as of the subconscious and emotional in symbolizing. In conclusion, their basic attainments, still vital to today’s research of symbols, are presented in relief