first of all, flags/hcs: gay and genderqueer for mani, butch transfem for vito, and gay for chester

flowers are gladioli for vito (they made a pretty little bouquet and according to my very brief wikipedia dive, symbolize "strength of character" and used to get tossed at winning gladiators in ancient rome, thus the name), and a green carnation for chester bc old timey gay symbol. manitoba's just here for trouble so he didn't bother with flowers (and I couldn't decide on a good one that wasn't way too headcanon-y)

as far as outfits:

I think you'd have to literally wrestle a suit onto manitoba and it'd last all of 5 minutes. I'm assuming prom has some sort of dress code so that's why he's wearing slacks, and at least the waistcoat has pockets he can shove stuff in, but someone twisted his arm to get him in that much. he's wearing his good hiking boots and a fancy fedora, and is mildly offended anyone would consider that "not dressing up" he tried to get a date. he failed. he's responsible for spiking at least one bowl of punch. his pockets are full of contraband.

I really like how the maroon looks on vito, I couldn't put him in a shirt without it feeling horribly ooc, but the white shoes make it pop. I think he's pulling it off, even if the jacket gets shed half an hour in. he would've had more gold on him but I was not drawing fingers.

personally I think chester got told to dress up and immediately swung femme. something something "kids today with their gendered clothes, back in my day we wore what we had and we liked it!" but he's been looking for an excuse to wear that dress for ages. he's trying to be grumpy about being stuck in a room with a bunch of teenagers but all the colors are making his eyes water (old gay guy cries at pride bc look at all these kids being able to be themselves, he is not immune) he will be freezing in like five minutes, if he's lucky he'll get to camp in a quiet corner in front of a heater, if not he's gonna complain everyone's ear off. if he plays his cards right vito throws his jacket at him instead of just leaving it on a table.