Not everything that is old is good. In fact, a lot of it is pretty wack. You need to dig through the annals of time to find the pieces worthy of being brought back. Even Jay-Z has a few bricks in his catalog, so don't expect every piece of clothing that came out in '92 or '52 to be great. It's OK to admit that something with a bit of lore behind it really wasn't great. The quicker you come to this realization, the more you'll be able to look at retro style through an objective lens.
Some old trends are better off dead.