Who needs a reason to look good?

Yeah, that's the whole being confident in your own skin thing. Tricky. Why not try clean, neat casual clothing first, like jeans/slacks, nice shirt, good shoes and put on a nice 'internal' suit first, good manner, curtesy/politeness, easy demeanor, well groomed, etc. that reflects what you want to be, or the reaction/response you seek from others. For those not terribly fond of the limelight/attention, any forced affectation will be pretty hard to carry. Sometimes it's just easier to blend in, depending on town, city, country. Sorry, got lost pondering your predicament. Hmm, tricky. Good luck.

I totally get where you're coming from. Try to remind yourself that:

a) life is fleeting. We're only here for a brief moment, so why let lack of confidence stop us from doing what we want to do?

b) if anyone judges you for your fashion then they're a sad cunt and their opinion is therefore meaningless

:)