I'm actually laughing at this thread. So funny to see my n00b questions from back in the day... :laugh:
Read periodicals, just don't limit yourself to the American ones. GQ and esquire are great but they also have international versions too. GQ Italia is a great one. The translation is a barrier but you can always google it. Pics are worth a thousand words and you'll get a very good understanding just by studying them. I'd start there. Money is not a factor and you pic up on mens fashion feel the source, Italy being one of them.