Daniel Patrick Moynihan specialized in the shapeless hat. I got this one from a Connecticut shop called Noggin Tops; it's made by Hanna.
It was a weird day of snow showers and meteorological mayhem. Camel hair blazer from the late great Huntington of Columbis, Ohio; I like it because a) it fits and b) it has black buttons embossed with some ersatz crest, instead of the usual gold.
The vest is an Orvis number that I have in fact worn fishing; elderly Rooster knit tie; Orvis tattersall sport shirt; LE chinos in one of these new configurations - "Authentic" or "Heritage" or some bumpfy name like that.
And Commie-stompin' Filson boots I bought off a clothing forum guy.