okay so you know the game yume nikki, right? the old rpg maker game where you walk aimlessly around a dream world. it's a classic. go play it. anyway i was real big into that game during my teenage years, and like any enjoyer of completely normal fictional men my favourite character was good old seccom masada-sensei.
yeah that guy. mister googly eyes. in fairness i think he was the only character who was both probably male and definitely humanoid so of course everyone was into him. yume nikki doesn't have much as far as concrete lore or canon goes, which means it's a prime sandbox for people to Make Shit Up in and i was one of those people. my yume nikki canon was pretty goofy, honestly. i wrote a couple (well. one and a half. i never finished the second one) of what i guess are still fanfics though they were in more of a script format rather than prose. i think i still have them somewhere so maybe i'll go dig them up at some point. anyway, for whatever reason i ended up giving masada a big rainbow ten-gallon hat (the prompt for this story was "western" but that only half answers the question) and ever since then the imagery just kind of stuck.
he even got an ask blog! i haven't updated it in a literal decade but it still exists. you can get a glimpse of my old headcanons for the other characters, too. you can also see some concrete proof that even at 20-ish years of age, i did not know what "drank" was. please don't own me too hard.
so yeah that's the interesting part of the story. why a gengar? i like ghost pokemon. i don't know if i'd necessarily say gengar is my favourite anymore but it certainly is very Shaped. i wish i could be that shaped. why the glasses? i wear glasses. i used to draw the googly eyes in there too but i'm more about the white lens superhero mask type look these days. it's not super consistent, though. i do what i want.