A few additional thoughts and cautionary notes about this project:
1) I’m not looking for cliche or novelty typefaces nor literal representations of what a person wears or what they look like. I want you to create a legitimate, useful, well-crafted, well-conceived typeface you and I can both be proud of—maybe even one that gains traction and earns you some industry clout (and money!).
2) Keep in mind that there’s a line between representing the essence of a person in a creative way and making fun of their physical appearance. Do not cross that line. You and I both will have to face them at some point.
3) In the end, the goal of this assignment is to create a distinct and useful typeface, not a caricature. Let that guide you when things get murky and indecisive.