I guess Bart wanted a bunch of hats so that he could fit into many different social groups. A lot of kids try this these days. How many times have you shook your head in disappointment as one of today's rebellious youth walked past with a skipper hat on? I mean, come on! We can't all be Alan Hale!
But Bart has a real problem, judging from the cover of this book; all of his hats look the same! I mean, what can you do with a big ol' red hat with feathers? Not much, except maybe be a musketeer. Or a pimp, of course. Yes, a pimp. Clearly Bart Cubbins aspires to pimphood. So here he is, pimpin' around and bein' all pimpy. Well good for him! More power to the pimpfolk.
Read this book. It's all about changing identities in a modern time. I suggest it as required reading for all Sociology 101 classes, and for a light, enjoyable read. Especially if your life goals include "getting a stable of foxy whores."