Barry Keoghan in LV
This just reads so cheesy to me. He's the guy in your high school who wants everyone to know he's rich, but also wants to come to the party you're having in your basement, so he has to walk the line.
Deacon Philippe
The aforementioned party is in HIS basement, so he can wear his PJs.
Milo Manheim
Milo is the son of Camryn Manheim; he's an actor (School Spirits, among other things). This looks like an old map someone spilled ink on, and yet weirdly I like it much better than either of the previous two outfits.
Zack Lugo and iann dior
iann named himself because Dior was his favorite seemingly unattainable brand. I wonder if he feels like he's cheating on them.
Blake Gray
He looks nice, and also it'd be easy to cover up a murder in that outfit.
Charlie Oldman and Dylan Sprouse
I believe Charlie is the son of Gary Oldman, and Dylan Sprouse is Dylan Sprouse, although he looks like he had to come to the party after having his pupils dilated. He needed nicer shoes.
Steven Yeun
Steven Yeun: confidently underdressed, also possibly relieved he got off this light.