How do I learn how to dress myself?

[Kalhoun]

@Stark Raven Mad

There’s a BBC show called What Not to Wear that AFAIK gives pretty sound advice (I’ve only seen two episodes, though). They’ve also come out with a book.

Sorry I couldn’t offer more input, but I don’t crossdress much.

I second that. This show gives you the basic do’s and don’ts for what you want to emphasize or minimize. The people are usually very happy with the results.