Step 5: Choosing your font
Font choice is not just aesthetic here. It is structural, and it is worth spending time on before you commit to a piece of art.
ASCII art relies on characters aligning precisely on a grid. Every character is assumed to occupy exactly the same width this is what is meant by a monospace font. In a proportional font, narrow characters like i take up less horizontal space than wide ones like m, which means columns will not align and your art will look wrong. This is why monospace is non-negotiable for ASCII art. It is the same reason code editors default to monospace fonts.
Beyond the monospace requirement, individual glyph design matters a great deal. Diagonal lines, borders, and connected shapes are drawn using characters like \, /, |, and +. If your chosen font renders any of these poorly if backslashes sit at the wrong angle, if the spacing feels uneven, if the characters do not connect visually the way you expect your art will look wrong regardless of how carefully you drew it.
Do not assume your existing site fonts will work. The font used for body text on this site, Special Gothic, was tried first and rejected. The header font, Alagard, was also tried and rejected. Neither communicated the right aesthetic, and neither handled diagonals in a satisfying way. The font that works for running text is often not the font that works for ASCII art, and it is worth approaching this as a separate decision entirely.
The font used here is a Tandy font from the Ultimate Oldschool PC Font Pack, available at int10h.org/oldschool-pc-fonts/. This pack is an extensive archive of fonts ripped from vintage hardware and software. The Tandy font was chosen specifically because it handles diagonal characters well while retaining the old hardware look. When evaluating a font, try a test string that includes your most commonly used characters before committing if the font makes them look weak, misaligned, or wrong, move on.