The more answers I read, the more I think there's more levels to this question than I had initially understood it.
My first response is very much in line with something I talked about on another thread months ago - that style is in the head. Or, generally, it's all about confidence, knowing yourself and knowing why we wear something (in my case - literally why and how some combinations came about).
That's something I've been thinking about these days again. From the point of checking the reaction of others to know if I got it right - I still say I don't care. Even when my husband is not to keen on something I put together, instead of feeling disappointed, I'm a lot more cool about it - because I feel I know myself better and why I present(ed) myself in a certain way.
I'm aware that my choice of words - presented myself - indicates there is a level of caring about what others think. True. In this week's WIW I've shown the outfit I wore to the parents' meeting at school - deliberately put tougher to present me as someone who'll take things school related seriously. I did want to send that message - yes. But, I return to the "not care" bit - I came up with the best thing I could for the occasion and did not care about whether others really perceived me like that or not - because I did the best I could and felt good about that.
As for appearing on YLF and perceptions by *the others* here - that to me is a different world altogether. In the outside world I'm on my own and have reached levels of dressing confidence thanks to - to a huge extent - caring about what others say here.
To sum it up, I will always care about reactions in the sense that I will dress ocacsion/time/place appropriate, but do not care about reactions to know I got right or wrong. On YLF, I ask for the feedback, so I do care and will care as long as I'm here.