Spendthrift, it probably isn't for you.  It isn't for everybody.  I was brought up on a constant background of music, both jazz and show tunes, Sinatra, even chaps like Andy Williams.  I remember songs like 'Moon River' just as well as anything by The Beatles.  My father was sixty years a jazz fan so I had a kind of mentor - although it was really Muddy Waters, B.B.King etc. that I began with before moving onto Parker and Coltrane.  There's really only one 'Bop', though, covering the bases.  I can take or leave a good deal of it nowadays.  I simply like melody and a certain amount of wistful romance.

Spendthrift, the jazz connection to Ivy League dressing has - arguably, to be certain - been overdone: Davis in the Green Shirt etc.  It's become too easy - almost an ingrained - image.  There are others, not invariably linked to jazz.  Steve McQueen springs readily to mind.  Once, it was fresh and newly minted, but that fresh is a long while ago.  On my last visit to Chiltern Street (ten summers ago) John was playing Duke Ellington.  (Or someone was).  Having said all that, it still seems the right - indeed, the only - music to run alongside The Look.  Paddy and Jim, however, JFMs old chums, are opera buffs.  Pad and I exchanged one or two convivial e-mails years ago about Lucia Popp.

I don’t feel good commenting on JFM’s original post, or some of the other posters following him, as I wasn’t on here back then, but with all due respect etc. I’d be dubious of anyone remembering or referring to themselves as hip, cool or whatever. It’s not enough to declare yourself as those things. It’s for others to see it and decide if you were/are or not.

My personnel vision of Ivy is heavily linked to Jazz.

I see parallels between the music, graphic design, art, films and clothing. An interest in one may take you to the other. I like that it's all very subtle too. It's not about designer labels and big in yer face logo's.

The casual elegance the USA offers - of loafers, madras shirts and seersucker jackets - sits comfortably with the relaxed club environment jazz music is played in.

When I think of the Jazz Messengers I see sharp, 3 button suits, button down collars,, Reid Miles album covers, New York and late night clubs.
Just like I see long hair, denim waistcoats and motorbikes associated with heavy rock.

I am in no way saying the two are mutually exclusive. My experience in many UK jazz clubs reflects this.

Alvey, I'm wholly in sympathy with all you say, aside from the possibility that the flagship approach sounds a tad contrived. 
But, yes, certain aspects of jazz and Ivy League do fit together, jostling for space in my enfeebled brain.  As I was saying to our Gibson (elsewhere) I truly the dig that half-reality, half-fantasy NYC-Soho in the 60s-Paris of Piaf ambience: all coffee, shirt skirts and corduroy jackets.  All gone, needless to say.  Black, white, queer, straight - throw it all into the mix.
Oh - no vegans allowed.

The relevance of jazz to Ivy as said below, is overstated in the U.K., the gentle influence  of John Simons is probably a lot to do with that and why not? You can take the idea or leave it after all. At the risk of steering into the rocky waters of race and culture, the jazz connection is more palatable this side of the Atlantic which, whatever some may say, is a more inclusive place. Even those who don't like jazz will recognise it's predominantly black origins and it's influence on subsequent types of music. Some Americans feel more comfortable celebrating the elite white lifestyle that hatched the Ivy look ... their choice.

It took me a long time to learn to appreciate jazz, regular exposure leads to it seeping into you as you start to recognise different tunes. I won't pretend that visits to John Simons and reading this Forum didn't play a bit, it all makes you want to find out a little bit more. Like Tim I favour the bop and hard bop era because I like the beat that underscores a lot of it, but there's plenty of other stuff on the horizon waiting to be discovered. Being rather old fashioned I collect CDs which are more palpable and satisfying than a download, but not as delicate as a vinyl collection, I can see the attraction of vinyl though. Playlists and best album recommendations need to be duly noted and then if necessary completely ignored. I've discovered some great stuff this way and also ended up buying some real shockers that quickly found their way to the charity shop - Coltrane's 'A Love Supreme' springs to mind, it was mentioned on here recently and cited in the Penguin Guide to Jazz as JC's best work, well everyone's entitled to their opinion. One of the great things about Spotify etc is being able to check out recommendations for yourself.

One thing leads to another. I'm even interested in things that aren't linked to Ivy clothing. I love motorcycles, but I can't abide heavy metal, it's better than rap though, but there again anything is.

Yes everything Woof says makes complete sense.

*Apart from heavy metal music being better than hip hop. Which are the deranged ramblings of a madman

Seriously, the only deficiency with bop (and bebop) is it can lead you up something of a blind alley.  Parker came, went, changed the entire face of the music (not all black musicians referred to it as 'jazz'), not entirely for the better. 
Same with listening to much Blues.  A black guy (who'd backed Georgie Fame) once gave me a fair bollocking on that score.  'It's all you white boys know...'  He was brusque to begin with, passionate to be certain, mellow after a while.  I took in everything he had to say.

>They're too busy checking their text messages/looking at Tik-Tok videos or simply focussing on their next takeout coffee.

too true.

Re: beginning of this thread.  I've dipped in and out of this forum, so sadly haven't kept up with everything but was Taylor McIntyre one of JFM's old handles?  Couldn't keep up with all the aliases and a complete list would be very helpful.

I think Taylor wrong on the trad/i-gent reason given or thought for black musicians to be wrapped in Ivy.  No one thinks they were "aspiring" to any sort of middle class respectability (by way of what was once a "uniform" for the Ivy League) certainly.  Not persuasive.

For some - style.  It looked good.
For others - perhaps Lewis, Jackson, Heath, Kay (for instance) - it was something more to do with public presentation.
With yet others - availability and affordability.