"Leopard-Skin Pill-Box Hat" is a satire of materialism, fashion and faddism. Done in Chicago-blues style, the song derives its melody and part of its lyrics from Lightnin' Hopkins's "Automobile (Blues)". Paul Williams writes that its caustic attitude is "moderated slightly when one realizes that jealous pique is the underlying emotion". The narrator observes his former lover in various situations wearing her "brand new leopard-skin pill-box hat", at one point finding his doctor with her and later spying her making love with a new boyfriend because she "forgot to close the garage door". In the closing lines, the narrator says he knows what her boyfriend really loves her for—her hat.