I dunno, I think you could do some pretty cool SWD stuff with what you have (as long as your current black jeans fit well). Vintage-fade denim jacket + heather grey t + black jeans + boots = easy success. And you have a beard too. There is so much visual interest potential stored in those wispy tufts bro. Since we rarely see you in such casual clothing, it can be difficult to imagine how you intend to channel the sort of looks that kgfan, for instance, pulls off.