I skimmed this thread to see if anyone 'got it', but so far, didn't see the light bulb.
The thing is; he wanted her to WANT to have more buttons - in a sense, he wanted to implant an alien 'want' into her, without him being the bad guy or having responsibility for doing so. Basically it's the passive-aggressive take on controlling and manipulating people; NOT DIRECTLY STATING that he wants more, is the key.
Because he doesn't simply want her to WEAR MORE (that's never the issue) - he wants her to WANT TO wear more. He can't of course order her to want to wear more (it's an oxymoron and an impossibility to want something because someone wants you to want something, because it's not a real want, you are simply obeying someone else's want, not expressing your own).
It's like trying to obey a command to not obey commands. Can't be done. The same way if someone orders you to be 'yourself' or 'natural', it's impossible to obey, because if you obey, you are immediately doing something 'not-yourself' and 'unnatural' (because instead of just expressing what you really are, you are obeying an order - so if you do it to obey, you are not really doing it, so you are not obeying, so .. it gets to be a paradox).
Because he can't order her to want to wear more, he tries to manipulate, imply, hint and lecture her into realizing that she should have such a want, although it of course can't officially be a requirement (if it was, it wouldn't be the same thing, because a want that comes from an order, is not a real want).
It's like trying to create false motivation - some people have it (the annoying fellow worker) and some don't, and basically, she is being warned, that if she doesn't have it, well, the career might not flourish..
It's all about the boss wanting the employee to WILLINGLY bend to his will and expectations, and it's just not the same thing if she is ordered to wear more. Then she's not doing it out of her own free will. He wants her to obey an unsaid command, he wants her to basically give him her soul by adding more buttons out of her free will. And when she doesn't, it annoys him, because he doesn't have 'full control' until she does. He doesn't have her complete obedience and faithfulness - he only has her surface obedience, and he wants it all.
I hope this clarifies what was going on in the movie.
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