Una, your brain is on fire today! What a powerful question. I'm trying to clear the weeds of delusion from my head to get at the answer.
It's so obvious when my clothes make me feel bad (and of course I don't want that), but I can't say I ask my clothes to make me feel good. I don't ask them to make me feel a certain way about myself. I'm not into, for example, "Hey! I am cu-ute!" (and I never use the word "hottie" either, btw - hehe).
I do take any number of things into consideration - like dress codes, authority, accurate advertising, and keeping the *native* traditions alive - but I don't think they're the main thing honestly... Come to think if it, paying too much attention to those considerations may have been a source of dissatisfaction in the past.
The one thing that comes to mind... well, as one of my high school beaux observed, I need to be entertained... (Man! So cutting! I should have paid more attention to the farmer's boy!)
Anyways, yes, cutting but true. And thus, I don't suppose, my aversion for "safe" outfits. My need for quirkiness. Just looking nice and pretty is a horrible torture for me. There's nothing to think about there.
Ok. Well, that's my answer for now: I want to feel entertained.
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ETA: I'm already back after reading more posts. I do want to feel - even when I'm alone - like I'm not only in the swim of things, but that I'm at the frontier edge. No velour lounge suit with words across the butt for me. That is so 90's.