I’m fat, hairy, ugly, loud, opinionated, have indifferent hygiene, smoke a stinky pipe, and wear a fucking fedora. Yet young co-eds less than half my age flirt with me all the time. Why? Because I am confident, and because I have a unique style which is purely my own.
The key is to remove any context by which people can judge you. If you dress in a particular style – goth, preppy, counter-culture, whatever – you’re inviting people to judge you by a yardstick against which you can’t possibly measure up. To avoid that, you need to develop a style which is entirely your own, and is sufficiently different that people can only judge you against you.