People with screws loose tend to go for the rockabilly look, both men AND women apparently.
Rockabilly usually has some (dweeby) attempt at edginess, cutesy skull print on a swing dress, visible sleeve of tattoos, that sorta thing. Dylan's trying to go for a straight up Doris Day musical.
The pink purse clashes with the dress and makeup. I also don't think the heels match the dress. I'd either go with nude pumps or a bag that matched the ivory pair. The hair is juvenile and the less said about the make up the better
Completely agree - couple of additional notes;
The pink bag is his day 365 bag from Chanel. More specifically I think it's this Moroccan leather classic Chanel:

So yeah a >$10k bag that he bought as a gift to himself for narcing his way onto Broadway for a star studded show all about how great he his? I'm sure he'll be swinging that from his arm no matter how much it clashes.
As for the dress - I'm in mixed minds (well, not about the dress, I can't picture many people successfully pulling it off and Dylan certainly doesn't).
He seems to dress like a weirdly slutty clown skeleton for red carpets, which is often at odds with his preferred styles, but I can't decide if it's because he gets told what to wear or if he just thinks he needs to attempt to be an
avant-gardiste de la mode on the red carpet. If it's the former (he certainly was forced to wear his merch to rehearsals) then it being Mommy Kate Spade's explains it. I wonder if he gets free dresses or his wranglers are buying them for their investment? He sperged so much about the Chanel that I don't imagine he's regularly shopping for gowns.
As for the makeup, Laurel Charleston is low key a big deal, she's being doing stuff for Melanie Martinez and Doja Cat as well as a variety of editorials (and weirdly is also a classical composer). Also claims to have done Dylan's makeup like two years ago as well.

(
I can't archive, I'm having twitter issues at the moment). Laurel is also trans; dunno what agency but whoever picked her has their finger very on the pulse about what's cool with the youth (which is amusingly at odds with Kate Spade). I think this makeup looks crap because it's too restrained/pulled back so it's neither glamour makeup nor weird avant garde makeup, but I also can't imagine Dylan in avant garde makeup going well, he's nightmarish enough as it is.
Long-time lurker here. Thanks for all the contributions and background that have been posted. I was a little surprised that the worst images I've ever seen of Dylan haven't been circulating. There may be more hidden gems if one looks at other professional photography sites covering his events. Isn't this a face deserving of free makeup and skincare endorsement deals?
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Additionally, I think his mom is divorced, and it's intriguing to me that she neither attended nor was mentioned (afaik) at the 365 Days of Girlhood farce. She's probably angry about being misquoted and twisted into some super conservative religious zealot, but maybe that's a discussion for another post.
Oof. Looks like that scalp scar isn't healing up - don't know if it's his hairstyles (which still look uncannily like a wig even if it's his "natural" hairline) or just because he eats like shit. Laurel really spackled it on him (I guess she made him up for TV?) but between the skin breakouts, stubble breaking through, cracked lipstick and every single wrinkle highlighted he is looking rough.
Speaking of which on top of the aforementioned eating like shit, not drinking enough water (and maybe drugs?) I wonder if his breakouts are also in part because he's picked up that "sleeping in his makeup" habit? He mentioned before he'd slept in his makeup and then touched it up in the morning, plus I bet he's the sort of idiot who'd make matters worse by using a really harsh toner and then slapping on a bunch of thick emollients and various expensive scented serums when he finally does take it off. (I'm ready for his "Whatever Happened to Baby Gayne" arc)