I generally have huge (HUGE) problems to find something that looks okay to me AND to other people. I hate shopping, too. But willpower gets me through it, kind of. I just try to find something that does look good, but isn't too much of anything. Plain but hip ish you could say.
I don't have many clothes, but most clothes have colours that are easy to match. Like, I have one pair of jeans that looks good with anything brown, yellow, and red, and another one for flashier colours like green or purple. Then I have a black pair that looks good with pretty much anything. That's three pairs of jeans. Then I have one black belt that looks good on pretty much anything (except with the black jeans), so I'm wearing it all the time pretty much. As for tops, I have two... what are they called, vests? They're like sweaters, but with a "zipper" in the middle. A black one which looks good on everything (except with the black jeans) and a purple one (which is good on the black jeans). Then I have some neutral coloured basic tops and that are pretty much all of my clothes.
The only reason I try to look fashion-ish at all is because it just makes things so much easier. Others seem to accept you straight away. They probably think like "Ooh! She is one of our kind!!" and come to mix. I prefer spending some extra money and going shopping. I could choose not to spend that money and not go through the trouble of shopping, but I do it for the bonus it gives me when it comes to socialising...