I didn’t know this meme originated from Jenna Marbles and that’s sort of off-brand for me but i don’t care.
“homeless man” - punk-esque cut-off pants and shirt, patch and studded vest, ladder-laced boots. This would probably be a default hot summer day outfit.
“12 yr old boy” - interpreted as vaguely mall-goth with fancy boots and a long coat. The middle-parted ponytail reads geeky and maybe more “innocent” to me.
“Hooker” - interpreted as subtly leather fetish-esque with the tight pants and leather jacket Drawing his thicc-ass legs without making them too feminine is a struggle.