I almost always go outside looking like this, regardless of where I'm going. I've been overhauling my wardrobe for this, in fact. It's been a slow process, but I have enough slacks, button down shirts, and blazers to get me through the week. I just need a tan fedora, preferably a 1920's style fedora (my black one is a 1950's style fedora), and a new overcoat, and I think I'll be set.
Call me a yuppie scumbag, but be warned! My reply will be (in short): "Sometimes I drink like it's the Prohibition all over again and I just don't give a damn about no Volstead Act. Now it's just a matter of looking the part."
On a side note, cigars and liquor were excluded from these two pictures for a number of reasons, despite the fact that they are my two favorite unhealthy vices. Firstly, I'm kind of running low on cigars. Secondly, I need to conserve my liquor. Something as silly as getting Manda to get an updated picture of me whilst we walk to an ice cream parlor did not denote the necessity of a delicious cigar and public intoxication.
There is now enough retro 1920's fashion on this forum. There could be more--there could always be more, regardless--but the current amount is sufficient for now.