This leads to other aspects of 'cool' - or its opposite.  Games can be played with others' perceptions.  Take the humble duffel coat.  Wear one with flat fronted chinos and dirty bucks you'll look about as square to the average Englishman as you can possibly imagine.  But you know you're the only game in town (Warren Beatty, right?) and that's what mostly matters.  I think a younger guy in a well chosen anorak could look exceptional so long as it was teamed with the right gear: maybe chinos and loafers.  Anyone over the age of, say, forty might be pushing it a little, but, hey, you're as young as you feel.  But true Ivy is, if not exactly square, then a bit odd in some ways, especially beyond its time and setting.  I suspect the English now have difficulty getting it right.  The long shadow of 'skinhead' and the fashions that followed is ever present: hence the ongoing love of the G9, the laurel wreath, tasselled loafers etc. etc.  Middle age perhaps allows one to take a step backwards.  If you know what I mean.