This is probably a direction I should go. I've never been a big fan of the open collar/sport coat look, but I think the turtleneck could work. Right now, when I wear a sport coat, it's usually over a crew neck sweater, but I might have to consider a turtleneck in the near future.
I saw a Studebaker President the other day with the most amazing interior. I wish I had taken a picture. It had this vertical striped cloth that looked like the sort of thing some of us on here have pants made of. It was well worn and clearly original, but just incredible to see.
The Healey in the middle picture is from a local Portland dealer, Avant Garde Collection:
His photography is spectacular, and I think in many ways this VW Bus is the ultimate...
I have to comment on gray shirts. I have a couple of them, and I wear them with either navy blue slacks, or once in a while jeans. I think they look fine, but as mentioned above, they are not particularly versatile. Still, I think they have a place.