I would wear red socks with every outfit - make it my signature look, like Tom Wolfe's white suits.
That sounds great. I think that you should try it for two weeks. Then decide if you...
I think that if I were to buy a jacket like that, I'd just get one of those "fleece" (plastic) ones from REI or Patagonia or some such. I can't see any reason to buy that in cashmere. On the other hand, I don't wear track style...
Agreed, I consider myself a preppy. I believe that people like me have suffered "dim mak" at this point in the thread Although I do not own any J Crew clothes, I think that their catalog is great.