I seem to recall these were a kind of canary yellow.

Wearer considered himself pretty much at the cutting edge of hipness.

Strange one isn’t it?
My immediate thought was that socks with boat shoes is just wrong.
Then I read Patrick’s post and agreed with him entirely.
Then I remembered that I own a pair of winter lug sole. They look great with thicker wool socks. Not quite right with thinner cottons. And would be just wrong without.
Mind you, my neighbour often sports shorts and T shirt with grey socks and a full English brogue. So I’m always going to do better than that.

Perhaps a matter, once again, of context.  This chap ran a clothes shop (actually more than one) in a rather dull town in the English Midlands.  That, if I may say so, is always one of the potential drawbacks of Ivy in England (at least outside parts of London): it risks looking like cosplay.  Nothing absolutely wrong with that - it's fun - but it should probably be borne in mind.  I've seen guys wandering around in stetsons and boot-lace ties: often classic car devotees.  But it can look, well, comical. 
Gary Jobson would be a different matter entirely.

I go sockless in loafers, boat shoes and sneakers.  I'm not sure about sweat attacking leather but would consider it a possibility.

I think Royce were once favoured amongst certain of the UK Ivy fraternity.  Falke seem most common, followed - perhaps - by Burlington and Pantherella.  But M&S did a very comfortable charcoal sock.  These have outlasted the Falke.  Wouldn't mind trying Wigwam.

Sockless yes.
Sockless whilst wearing a tie - iGent.

I can only dream of wearing boat shoes sockless. I'm currently in northern Finland, close to the Russian border. The temperature is -15C and earlier today I was outside wearing two pairs of socks. I can just about understand sockless in Rome but not in Northern European countries except for maybe one week in the summer. It's an affectation.