I'm wearing leather pants

I saw this guy on the train... derby, heavy, weird black gloves, tiny dark sunglasses, long black trench, flavor-savor, dark wine-colored shirt, black tie, and leather pants. Oh, big black boots and a heavy-looking, somewhat beat-up metal briefcase. And he had this look on his face, like "Go ahead and look... It takes hours to get this just right."

The other doodles were attempts at a self-portrait, but as a young kid, but with some adult attributes (i.e., bald).