White jeans? The blues are the more classic representation of the look. Hopefully you're already working on the 'stache.
I'm not at all a bike expert.
But there are some nice features on that bike. The seat alone (even in its worn/cracked state) could get you more than half the money back. I know the vintage/refurbed bike market is pretty big in Louisville, I'm sure it is similarly popular in some parts of NYC.