This is almost a game we're playing, wilfully blurring the edges between the original style and its jazz evolution.  The more I study the 'Take Ivy' images, though, the more 'uncool' it seems and the happier I am, because we can drift many miles away - even in England in 2009 if we have the will - from the traditional English notion of 'cool' which is either, as Gibson Gardens has noted, devalued currency else linked - at least tenuously - to tribalism and aggression in a rather Konrad Lorenz kind of way. 
I keep on taking steps sideways, looking over my shoulder as I go for deviancy.  This is not quite about rediscovering some form of Ivy purity - Lewis is probably right to be sceptical here - but just trying to analyse the psychology behind those early to mid-60s student dress codes, some of which I'm sure, from reading other threads, few of us would willingly follow.  Some of us, of course, are too old and now taking into consideration 'Esquire' strictures on attempting to retain a campus dress code.  Back to personal evolution, then: from the college sweatshirt and the yellow slicker to tweed, brogues and bicycle clips: from 'young' to old fogey, in fact, to borrow a fairly interesting sub-cultural reference.  To look like the first President Bush?  Not bad!