Are you afraid of things changing? Trust us, it sucks, but the only way you'll enjoy the generation you live in is to gradually accept the new. Now, we're not saying that you need to listen to every one-hit-wonder and dress in every piece of clothing that a popstar or rapper wears. But if you're trapped in the past, you need to come to terms with the fact that "the good 'ol days" aren't coming back, as shocking of a revelation as it might seem. So, when you dress head-to-toe in pieces from a long-forgone time period, you seem like the nostalgic guy also keeps mementos of ex-girlfriends he hasn't talked to for seven years. And that our friend, is a touch irrational.
Don't wear old clothes just because you're afraid of change.