i'm a nerd. i'm also someone who ended up in a completely different culture. one where, i realised, i looked just plain stupid. i changed. now, i think, i dress pretty well.
but it was a very personal journey. and i had to think hard about a lot of very important things on the way. i didn't wear a t-shirt and jeans just because i was clueless. it was also a statement about what was important to me. which certainly didn't include brands.
balancing that and finding my own style took a lot of time. it was also very interesting. and i now enjoy thinking about clothes (in a broad sense - it's all about context and culture; it's only about money in the sense that culture and class are deeply linked).
i'm not sure how much of that you're going to get in an "advice column" format. and i'm not sure if you're expecting the kind of deep emotion behind "anti-fashion" that a lot of people have. i think you may be surprised at people's (negative) reactions...