Slumming It

"I want to live like common people, I want to do whatever common people do."

- Pulp, "Common People"

So, you're a Rich Idiot With No Day Job, but you're getting a little bored with your idle life of lounging and spending. So what do you do? Pretend to be poor, of course! After all, if so many people are doing it, it can't be so hard!

Compare King Incognito, Secretly Wealthy, Prince and Pauper and Bourgeois Bohemian. A character doing this may or may not be Rich in Dollars, Poor In Sense.

Anime and Manga

 * In Sayonara, Zetsubou-sensei, Rin poses as an ordinary public high school student despite being wealthy enough to do whatever she wants.
 * Let's not forget that her brother Nozomu doesn't have any reason to be a teacher.
 * The idle rich have never even heard of instant coffee crystals in Ouran High School Host Club. One of them tries it and is delighted. "So this is why commoners drink it all the time!"
 * All over Ouran High School Host Club. The "commoner" Haruhi is so fascinating to everyone else because they're all so rich and high society that a normal middle class lifestyle is like a different world.

Film

 * Bruce does this in Batman Begins.
 * In Rodgers and Hammerstein's Cinderella, this is how the prince and Cinderella meet for the first time.
 * In Aladdin, Jasmine tries this, and very quickly learns that she knows nothing about life on the streets. Later, when she sees through Aladdin's "Prince Ali" disguise, Aladdin claims that he's a prince who makes a habit of going about the streets dressed as a commoner.

Literature

 * Mentioned in Witches Abroad: Nanny Ogg says that those princes dressing up as paupers always make sure the peasants don't get too close.
 * In Pyramids, Teppic reflects that peasants have more freedom, before correcting himself with "yeah, freedom to be starve, to be worked to death, to die of a horrible plague..."
 * In The Princess, the Crone, and the Dung-Cart Knight, Lancelot and Sarah arrive at King Bagdemagus' castle and the fashion-obsessed king is inclined to look askance at them because they're wearing such shabby clothes. Lancelot convinces him that dressing up as humble shepherds is the new court fashion, causing Bagdemagus to set about getting a "costume" of his own. He takes it so far that when the climactic duel is scheduled to be held in his Great Hall, the hall is full of actual sheep he brought in for the atmosphere.

Music
"And still you'll never get it right, 'cause when you're laying in bed at night watching roaches climb the wall, if you called your dad he could stop it all, yeah. You'll never live like common people. You'll never do whatever common people do. You'll never fail like common people. You'll never watch your life slide out of view, and dance, and drink, and screw, because there's nothing else to do."
 * Pulp's "Common People" (the page quote) describes a student from Greece who does this - and then skewers her mercilessly for thinking "that poor is cool":

Theater

 * Arthur Shnitzler's "The Little Comedy" (which was the basis for the first act of The Musical Romance / Romance): Two rich folk pretend to be poor to find love with someone real- they find each other, then have to nobly break it off because they're in love, and they can't get out of their web of lies. Then they later meet each other as themselves at a party.
 * In Camelot, King Arthur meets Guenevere in this way, intending to avoid an Arranged Marriage to her. It turns out to be a Perfectly Arranged Marriage, but all the same they find themselves singing "What Do The Simple Folk Do?" in the second act.
 * Miss Dorothy does this in Thoroughly Modern Millie. She even has an "I Want" Song about it, titled "How The Other Half Lives."

Western Animation

 * The Dethklok band members in Metalocalypse attempt to be "regular jackoffs", before they realize they liked it better when they were basically gods.

Real Life

 * Historically, it was fashionable before the French Revolution for nobility to have picnics in which they dressed up as peasants and shepherds or for paintings to depict a romanticized version of the peasant.
 * Marie Antoinette also did this, and said (or was said having said): "The peasants don't know how lucky they are!" We all know how that turned out...