"No matter how hard it tries by rejuvenating neighborhoods like H Street, the strip that landed it the No. 6 spot on that Hippest Hipster Neighborhoods ranking, there are some structural barriers to D.C. which preclude hipness," argues Greenfield. These include: cost of living, size limitations, transience of residents, and "[n]o promise of glamorous success" (unless you're Monica Lewinsky or Anthony Weiner).
In a piece for Bloomberg View, Josh Barro takes issue of several of Greenfield's reasons, but agrees with her larger point and one specific overriding factor - D.C. isn't hip because it attracts professional squares. Says Barro, "[t]he real problem is buried deep in Greenfield's piece, and sadly it's not one that policy change can fix: Washington is boring because it's full of people who work for and around the government. These people may be insufferable (Capitol Hill staffers, lobbyists) or dull (bureaucrats, lawyers), but they are highly unlikely to be hip."
"The city attracts government nerds and sticks them in social situations where there is no pressure to suppress the boring. This isn't a problem that can be fixed with better planning policy. The only solution is escape."