coming from a complete newb:

I would look for cigars with similar characteristics (wrapper, filler, etc.) For instance, I recently discovered I like cameroon wrappers. So, I've started purchasing more cameroon wrapped cigars. There's a good thread about wrappers and their different characteristics on here somewhere. I have it bookmarked at home.

Something else that might help you out is on CI.com if you look up a cigar and scroll to the bottom, it will show similar cigars. Don't know how accurate it is, but it might help.