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An Urban Chestnut is what you leave on a hookers blouse (or any city dweller) when she blows you off in a St. Louis alley. Also, a St. Louis craft brewery which you may have visited before buying the BJ and depositing the Urban Chestnut.
Man, I had a couple of beers last night and totally gave my girlfriend and Urban Chestnut behind the Pita Pit.
A young metrosexual male, preferably with a man-bun and/or beard who dresses fashionably. He would be into the current fads or trends and always drinks complicated beverages when dealing with coffee or alcohol.
That urban chestnut will only drink local craft beer what a loser.