I might not normally agree with CC but I think he had a point with this one. It clearly demonstrates the direction in which a style can go however well defined it might have been in the beginning. So, the Jason Jules sockless in wingtips I cannot do much as I might display my skinny white ankles in Sebago loafers or boat shoes. Don't mistake me here, I'm far from being as buttoned up as some modernists/East Coast types I've seen photographed (more than in the flesh). I really don't remember the last time I wore a tie, even a dark knitted Rooster. Some degree of slouch is desirable perhaps - but not wilful slovenliness. As a matter of fact, of course, in England it's probably 'Sweatpants And Cummings' (what a cock, as 2RS might say!) rather than an adherence to a political philosophy with which few will now be familiar. Especially the monied gents of various Internet chatrooms.
Responding more to CC than you, but surely there was more Marxism on campus in the boom years than now. Students are on the whole, apathetic rather than the cancel culture woke raving lunatics they are painted as. They do wear sweatpants to school, this much is true, but this is the fashion of the day.
In that 'Take Ivy' period? I'm not sure. Maybe there were demonstrations against Vietnam or some interest or involvement in civil rights, but the 'Take Ivy' images are very similar to some I've seen taken in the late 1940s: young men oozing affluence and complacency. Maybe the type John Simons and his friends were hoping to sell to in and around London? I don't propose to get into the 'skinhead/non-skinhead/Spirit of '69-style debates/arguments again, just reflecting upon the type of customer JS hoped to be seeing coming through the door: more Bobby Kennedy than Joe Hawkins.