Anyone can smoke a cigar, but only overpaid corporate executives can smoke them knowing that they deserve to smoke them. A half pack of cigarettes worth of tobacco just tastes better after a long day of mergers, acquisitions, and dream-crushing.
That sense of cancerous entitlement inspired Thomas Pink's "Mogul Shirt." It's got a small pocket for a cigar on the chest, making sure you never are without a stogie when you need one. Just make sure you have a stack of $100 bills around to light it with for the full effect.