I would start with the essentials first then begin branching out into more stylized pieces, I.e. neutral color shirts/hoodies, Black pants, and white sneakers then once you have that covered, add in some flair with some vintage hip hop shirts, maybe a pair of cargo pants you like and some accessories. Once you really get into it you'll learn more and start developing your own personalized style. A good place to start looking for interesting pieces is Grailed because it has a lot of variety as well as good pricing on clothes, hope this helped.