The best advice that someone could ever give you is just be yourself, and if that means you feel the need to consistently dress like Mookie in Do the Right Thing, that's fine. But if you're dressing that way simply to imitate Spike Lee's cool '90s style, then you need find a new approach to your personal style. There are certain items you can wear that are "timeless": a blue oxford shirt with a pair of straight-leg jeans, or even a black pocket-tee. But if you're looking at a picture of someone else every time you place a garment on your back, then you need to do a little soul searching, and it has nothing to do with clothing.
It's better to be yourself than to imitate someone else's style.