these little buddies were drawn for a gum wrapper. the design never made it into production but these guys were fun to do. you have a gif file and a jpg file of each. the color is better on the gifs. this style is reminiscent of old computer 16 bit graphics. The orange is wearing chuck taylor converse, the official shoe of the counter culture since 1972. Most artistic type own or have owned at least one pair. Beat up black is probably the best type to capture angst and fun at the same time.
I guess my dream job would be drawing this sort of thing all day. it is a highly competitive market, illustration styles change yearly, like sneakers if t shirts. the basic printed t-shirt concept is around 40 years old but it is constantly being reinvented for the young crowd. Style in this age has become very diverse yet people want to belong to some group or sub group. each person wants their group to be the best, but ultimately we are just tribal cavemen, fighting for mating rights.