Define the hat band, and then draw the lid which is being worn in a backwards style. You will then draw in some of his hair that is poking through the sides of his hat, and then draw the rolled cigarette. A lot of gangsters like rolling their own cigs because they can control the flavor and strength of their own smokes. Anyways, draw out his baggy shirt which is a bit big for his build. Draw out the necklace and then the chain. Don't forget to draw out the cigar, and gold ring too.