Some stuff depends of your age. In my mid 30's I can pull off a trenchcoat but no way would I rock one when I was 19/20.
Also eventually you style should evolve to were you can look fly/professional while sneaking in little bits of your own personal style. Whether that's based on where you from, your (sub)culture, your values, etc. If you want to rock a leather jacket and boots on some punk rock shyt, do it. If you wanna rock a recycled hemp cardigan because you care about the environment, do it. They say rocking business wear and Jordans is low class, but if you love Jordans, who gives a fukk? You don't have to rock it every day but sprinkle in some of your own particular style.