Er, no. I don't remember typing the word "pirate". That would be your word, Pliny.
Dressing like a rock star could conceivably be "classic style" though. After all, that style of menswear has been around for over sixty years now. The Beatles and the Stones were very sharply coutured during the early 60s. Carnaby Street style in the mid to late 60s borrowed heavily from classic influences across several eras.
Whether one accepts this possibility would depend on one's inherent degree of conservatism. Rock star style (and of course I am not referring to the excesses of hippydom/psychedelia/glam here) involves mixing influences, which militates against stylistic cohesion, but does open up new aesthetic doors. This has always gone on - think of 19th-century dandyism, or gangster style from the 20s, which involved a similar mix-up and exaggeration of styles, designed to catch the eye and make an extroverted statement.
My guess is that Shoe Artist is well aware of the stylistic influences he is mixing together. I don't think his fits are happening by accident. I'll concede though, that it's risky and difficult to carry off.