There's a fun show, I think British, which I only caught the tail end of. It's something like A Week of Dressing Dangerously. A woman is challenged to wear these mildly outrageous outfits all week, and see the effect on her. Will she feel less inhibited, more confident, more sexy etc. after. I'll have to catch it again, because not only was it fun, but I think they're tapping into something that What Not to Wear is missing out on. Or maybe it's taking an idea in WNTW and expanding it.
I know several people (possibly all men) who believe you shouldn't care about what you wear, because it's Only for Other People, and anything that's about Other People is automatically bad. And I presume they actually think that they don't care about what they wear.
But I think appearance is part of the way you communicate with the world around you, just like talking, or writing, or blogging etc. And how you present yourself to the world, does feed back in to how you feel about yourself... even if you're just wearing sluffy jeans and t-shirts. You're still carefully choosing that I Don't Care What People Think look.
Which brings me to the topic of Caring What People Think. Anyone who's known me since, say, high school will know that this has been a Creed of mine for most of my life. But there are limits--sensible limits. A friend of mine once said "only crazy people don't care what others think of them"... and if you think about a really mentally ill person riding the bus, you know what she means. (Maybe Drunk People could be added to the list, but you get the point.)
And there's nothing inherently wrong with caring what others think, it's very biologically sensible. We live in societies, we are constantly engaging in non-verbal communication, and how we read each others signals probably made the difference at one point in time between getting skewered and surviving. Or being outcast and left to starve, and surviving. We probably have very strong drives making us want to *belong.*
So while I'm all for the "do what you want, to hell with Them!" attitude, and try to live a lot of my life this way... ease with the binary opposites. Taking this idea to the extreme is just as silly as always caring what other people think... and I would argue, it's rarely even done, because that's how illogical it really is.