He is pictured on a few US stamps of which the Scott 623 at left is by far my favorite. It is simple and bold, the creation of of Claire Aubrey Huston who also designed the Panama Pacific series. As a pince-nez wearer myself, I am impressed with Huston's accurate depiction of Wilson's hoop spring pince-nez.
I recently acquired a nice registered cover showing the 623 stamp in single usage.
Why do I call Wilson a man of the people? Because underneath the aloof academic persona was a man with very human emotion. I've been reading Woodrow Wilson by H.W. Brands and I found a truly touching section. Wilson's wife died and in 1914 and he was completely distraught and depressed. It was very sad. Then "What finally snapped him out of it [depression] was not any insight into the meaning of life and death but an attractive face and a pretty figure." (Brands, p. 65) The face and figure belonged to Edith Bolling Galt, the second Mrs. Wilson. Yes, President Wilson was quite human.
I highly recommend a website of unique interest: the Medical History of American Presidents. The one on Wilson is very interesting and sheds insight into his actions.