Nice call. Nothing beats a herringbone jacket, an OCBD, flannels, and a wool challis neat!
Could not agree more. My guess, most of us posting in the Trad forum get that same indescribable feeling from wearing classic Ivy / American clothes.
It is in the high 40s, overcast and threatening rain in NYC today, so I have on a pair of heavy khakis, thick Fair Isle socks, Sperry Chukkas, a heavy OCBD, Woolrich sweater and LL Bean rain slicker (long-jacket length) and couldn't love the feel of my clothes more.
There's something so - to me - authentic, real, basic, practical, timeless, comforting about them. They just make me feel good. That's it - I wear them because they make me that happy.