A clumsy attempt to be—not appear to be but be—a gentleman is admirable, because the ideal of the gentleman has moral content. A clumsy attempt to be cool is ridiculous.
Quote taken from this comparison (which I liked) of the concept of the gentleman with the concept of cool. I endorse the point as far as it goes — coolness is an ideal of style without moral content. Unlike other amoral excellences, coolness has always struck me as a bit of a fraud. It lacks not just moral content, but any content. Coolness can be standing there in sunglasses, having a counter-intuitive band name, whatever. Is there something in there more than personal magnetism, more than a kind of grift?