You bastard. Looks great. The button-up vest definitely works better.
He actually just asked where are the best places in Chicago to go. So I suggest an architectural boat tour (awesome, even in November), the Art Institute (American Gothic is there, I believe, as is Nighthawks). And I recommend The Conrad, especially as it is attached to Nordstrom, which will allow the OP to pick up some nice clothes too. You're welcome.
Somebody need some RRL raw selvedge size 30x34? Here's a good BIN:
Who the fuck gets rid of THIS? I thought TOJ was almost exclusively patronized by style buffs...
Then again... Balmain. You never know.