Sperg incoming, sorry.
I
really think he does.
The thing with stylists is that they're still dressing a client on a set budget. Brian is not a stranger to dressing men in womenswear:
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but he'll have had a brief and beyond "are you cool wearing womenswear" or "are you comfortable showing this much skin", Tom Daley would have pretty much worn whatever he was provided without really any creative input - he's not going to go "can we try this skirt with that top, I think it will look better". So the stylist can really showcase his skills.
The BTS was enlightening because it showcased how Ollie works with his stylist - he approaches the table with fully realised concepts (specifically instructing his stylist to track down an elaborate feather collar, he didn't just say "I want to have an angelic themed outfit"). He even sends pinterest boards of ideas (and probably not garments, but pictures of sexy biker chicks or sexy Russian Bond girl spies or sexy secretaries). There's very little creative freedom.
If Ollie sends you a photo of, hmm, let's say Diana Rigg in
On Her Majesty's Secret Service, wearing a couture Marjory Cornelius bridal jumpsuit, playing the only woman to ever marry James Bond:
View attachment 2977385
and says "Here's a budget of £500, make me look like that and also two other costumes, one of which needs a feather collar", well... you're basically going to have to resort to PrettyLittleThing because you don't have the budget or time to access designers or fashion archives and scour for something white and crocheted
and a jumpsuit
and that will fit Ollie's rugby lad frame. Thus:
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(Here you can see Brian desperately pinning the front of the £45 PrettyLittleThing jumpsuit together to try and stop it gaping apart over Ollie's massive hog torso).
I love your commentary on both those dresses - spot on. Feeding into that lets compare what Ollie was wearing with what he
thought he was wearing:
View attachment 2977405
Not exactly the same, but they're both white frilled dresses hitting at the upper thigh. Except the one in the right is
supposed to be that length. He doesn't realise that a woman who tried that on his outfit and had it hit there wouldn't go "oh cute, a short minidress", she'd go "oh I'm too tall to fit this dress" (especially if the flounce was hiking up in the middle like that). But in his mind's eye he's just picturing a pretty girl in a coquettish Summer party outfit.
This feeds into how Brian dresses him. Brian's presumably realised at this point that when Ollie is asking for something sexy (over e.g. his Riddler or Sherlock Holmes cosplay) he doesn't see how he looks, he just sees the idea of the woman he's trying to skinwalk that day. So it doesn't matter if Ollie looks bad or the outfit doesn't fit properly - thus why bother wasting time trying to style some creep who won't appreciate it, if you can phone it in and get paid the same anyway?
Edit: More autismo
I couldn't find the exact dress he bought (probably snatched off the bargain rack in New Look or something) but I found dresses of that type:
View attachment 2977725
See what I mean? If the dress fit Ollie it'd be more like this:
View attachment 2977727
Except it wouldn't because it still doesn't fit (the bust is still hiked up too high because the dress is getting stretched across Ollie's broad shoulders - I didn't even bother to try fixing that because at that point I'd essentially be morphing Ollie into having a woman's body)