Found this: http://us.suitsupply.com/en_US/suits/napoli-blue-check/P3832I.html and a great pair of Billiam jeans at Buffalo Exchange. They want about $100 altogether, so I'll dig through the archives to see if I have anything to exchange to bring that price down to 0.
Let's keep it ITP, but OTP adjacent. The only bars I frequent (or used to) are Midtown/Decatur(ish), so I'm no help on a place. As for a time: After work on a random Wednesday in late January/early February?