To be a Dapper Gentleman you have to have features that elevate respect, elegance, romance, sexiness, and most of all, charm and style. Dapper men in media history include Fred Astaire, Gene Kelly, Darren Criss, Robert Redford, and Christopher Plummer. Men with beards and a top hat in the 1800s are the origin of a man being considered "dapper". A dapper man is a gentleman, and will pay the bill on a date, appropriately respect a woman and compliment her when a compliment is needed. He is like a hipster in the sense that he does not need to try to have a keen sense of style in the appropriate setting. Darren Criss is the most dapper man I have ever seen. O my gosh! Did you see how dapper Darren Criss was on glee? I love when Astaire dances! His moves are so dapper! My boyfriend proposed to me as the sun was setting. He is so dapper! Why can't any guy on Jersey Shore be dapper once in a while?! [spoiler]Ahh yes, I see your point[/spoiler]