Mordvalaisten pukuja kuoseja, 1896. A book of traditional Mordvin costume patterns from Russia. via
The article The Lost Ancestors of ASCII Art shows works from a typewriter-focused magazine from 1893. The butterfly on the far right has been around the netz for a while, but the middle one (by the same author, Flora Stacey) and the ship (by Frederick Carles) are new to us at least.
Leetspeak and possible emoticons from 1890. Found by Koichi Yasuoka, who writes:
The article shown right is from The Typewriter World (Chicago), Vol.I, No.2 (October 1897), p.46, which I found in The New York Public Library. You see the sentense “he Said it would Be a thxng of beavty & jOy FORever” is followed by a combination of punctuation marks, a semicolon and a right parenthesis, which is one of the so-called emoticons nowadays. I cannot make sure that it was really intended to represent a winking smile, but I need to check Berkshire News (Great Barrington, Massachusetts) of February 6, 1890. How do you think about this?