There is a long anarchist tradition of stamp collecting. In most cases, receiving non obliterated stamps paid for the expenses. But often some comrade would start a collection and sell it to philatelists for the benefit of the movement.
Though many anarchists reached an international fame, it was very rarely that states would picture them, and whenever it was the case their philosophy was never mentioned.
Nevertheless, there are a few anarchists represented in stamps, the most frequent one probably being count Tolstoy, the author of War and Peace. The Spanish Civil War also occasioned a set of anarchist stamps, which were used for purposes of propaganda. There were also false stamps, for instance of Nestor Makhno.
The anarchist stamps that were printed in Spain during the 1936 Civil War are very rare and today very valuable. After Franco’s victory, people who kept them risked their lives.
Some of those who created those anarchist stamps and posters are relatively famous. Carles Fontseré (1916 - 4 of January of 2007) worked for the Spanish FAI, the CNT and the POUM. He worked with Salvador Dalí and Cantinflas and later was in Hollywood,
There has also been some exercise in imagination. New Zealand anarchist Bruce Grenville was the mastermind in the 1970s behind an extraordinary hoax involving the creation of an imaginary state: Occussi-Ambeno. See the stamps of Occussi Ambeno

More information
– "Bruce Grenville and the Utopian State of Occussi-Ambeno
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– Clifford Harper, Designs for Anarchist Postage Stamps: With Sixteen Portraits Foreward by: Colin Ward. A K Pr Distribution, 2002.