What seems to be a smiley from 1648 (top), written by the poet Robert Herrick, is most likely not. The same book contained more smilies (bottom) that indicate that it’s not supposed to be read as an emoticon. See Slate’s article for more examples and information.
A belt from ca 1680, symbolizing a treaty between the north American Turtle Clan and William Penn, who said “We meet on the broad pathway of good faith and good-will; no advantage shall be taken on either side”.
Not sure how well that worked out… Also, seems like the belt was copyrighted in 1905.