Clothing Demystified
Callista, ouinon, Crack - certainly nothing is wrong with a "uniform" or a simple selection of clothes that work for you. My goal here is not to prescribe good fashion, or to pass any sort of judgement, but to demystify how style works, so that its language is accessable without appealing to "fashion sense". A wardrobe that says only a handful of things is quite sufficient if it says all the things you want to say. But this is not sufficient for everyone.
SotiCoto - It seems that this type of tutorial is not necessary for your needs. But these are things I would have liked to know when I was younger, and I suspect they might be of use to others. As far as trial and error goes, many of us are a bit shy about making clothing choices, and might appreciate some guidelines that help us avoid ones that draw unwanted negative attention. But hey, different strokes for different folks, yes?
Callista - I'd say clothing is communication that many NT's seem to grasp easily. That doesn't mean we can't, or shouldn't, learn to speak it. It'd be like saying "French is for French people." But it's also for non-French people who want to learn French... even if you're learning just enough French to avoid saying something offensive by accident. ^_^
EvilKimEvil - Clothing, like any other form of communication, can be interpreted differently by different people. And the message that's received may be accurate or inaccurate, and may be liked, disliked, or even ignored. Part of this process is entirely up to the observer, and we can't change that part. But by being conscious of, and deliberate with our communication, we can still affect communication for the better. I think the two modes of dress you mention are a good approach, and copying your friends is a safe and effective way to get used to building outfits. ^_^
I found my all time favorite pants, Ben Davis 50/50 blend twill pants. You can get them online too from gorillagear.com. Much stronger and longer lasting than jeans and lighter weight. The 50/50 blend dries quickly, so they're better for hiking and camping, and they don't wrinkle. For shirts, I prefer snaps to buttons, you can take it off more quickly, and the snaps never fall off. Pendleton makes some soft washable wool shirts that are great.