I do have a schizo theory that his stylist only took the job because they're struggling (money's tight at the moment, so less people are hiring stylists - even some fashion houses are getting in-house staff to put together "edits" for shoots), and they know Ollie has no taste or sense of style. Thus they hate Ollie and take it out on him by dressing him atrociously, because he won't know he looks terrible. The frequent use of outfits that literally do not fit his frame lends credence - unless Ollie's stylist is blind, they'd spot that a mile off (being a stylist is actually a skilled profession, you won't get anywhere unless you've got an eye for detail). I can absolutely see Ollie thought he looking banging in that shitty jumpsuit, because "oh it's all white and it's lace and it's low cut, so that's a sexy outfit" and didn't even consider he looked like he'd wrapped himself in his nan's net curtains (and why lace opera gloves?! You can't just put on opera gloves and declare yourself classy, they're only ever formalwear or fetishwear/fancy dress and so the outfit has to be one of those. No woman walks around in opera gloves).
My alternative theory is that Ollie's really tightfisted and sets a rock bottom budget for outfits, which has forced his stylist to resort to Nastygal and PrettyLittleThing. Compare this with the person he's skinwalking:
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AFAIK Contra doesn't hire stylists. This dress probably wasn't that expensive (although likely more expensive than Ollie's entire look) but it fits well and more importantly was styled well. That wig is an expensive lacefront that Contra likely had styled at a non-insignificant price. The ribbon is good quality (unlike the shitty polysatin Ollie wrapped around his neck for that stupid Steampunk look). The fan is a wood and lace number, not a shitty Amazon plastic clacky fan that a two-bit drag queen uses. And the fake blood is stage blood, probably Mehron (not the neon red stuff you get in a Halloween shop) and there's multiple bottles of it - and it won't wash out, so Contra can't use any of these pieces again. Also the outfit is both cohesive (there's no doubt it's Marie Antoinette) and relevant to the topic being discussed.
Or to put it more succinctly: Contra wears Atelier Versace, Ollie demanded Contra returned the RTW Versace jumper he'd bought her after they split up.
I probably deserve puzzle pieces for this sperg (I think I'm starting to become the
@Nykysnottrans of PhilosophyTube) but Ollie's terrible attempts at dressing his hulking hogbody really triggers me.
youtu.be
Not on Olligail, of course. But like, I thought with the gloves and everything it was just objectively pretty and would look good on me lol. 
