You're right about loafers and socks - they suck. But it's necessity, as I'm afraid my school shoes met an untimely demise and going sockless isn't an option - for the forseeable future, tan tassle loafers are my smartest shoes.
I always associated both loafers and argyle with a preppy aesthetic - although they are, as you say, from different backgrounds. So I was rather hoping they'd sit okay together.
I also can't go completely sockless with these shoes because they are far too tight; according to the gentleman at the store the leather should stretch slightly over time, but until then they are simply not comfortable without a bit of lining. I understand you can take them to a specialist who'll stretch the leather artificially, in the proper way? Anybody know anything about that?
As for your wild socks? I'm sure it looks fantastic but I still deem it a guilty pleasure
At least tell me that when push comes to shove, you wear black socks with black tie