Don Draper
This is the kind of costume your guy can easily don (pardon the pun). It requires a few things that he probably already has: a gray or dark-gray suit (black will work if it’s tailored enough), oxford shoes, a white dress shirt, a tie, cuff links and cigarettes. As a bonus, he can walk around holding an old-fashioned tumbler glass (preferably filled with scotch).
Photo: AMC / The Nest