In fiction, it's apparently very hard for the wealthy to avoid being either a Rich Bitch or Spoiled Sweet, both are scorned by the average man. Many Genre Savvy characters spot this trend and hide their wealth. For some they've even been separated from the family, and are wealthy in name only. Expect these characters to be kind, caring and generally the opposite of a Rich Bitch, so that the reveal of their wealth is more shocking.
In Real Life, there are several advantages to attempting this. Large wealth disparity tends to create serious rifts in casual social interaction; friends of a lower income class may secretly resent you, or expect large monetary gifts and favors. On the other side of the coin, it is also hard to know who likes you for yourself, and who only likes you for your money (this is a reason many rich people only cavort amongst their own class). In addition, those who are known to be wealthy are frequent targets for lawsuits, and family members may even be targeted for kidnapping by those looking for a ransom. Hiding your wealth can prevent many problems like these.
Compare King Incognito, where the secret can be wealth, but must be that the character is powerful in some way or another, and Slumming It, where this is done for fun. See also Non-Idle Rich, for when the wealthy person works a "regular" job for fulfillment and/or helping others. Contrast Mock Millionaire.
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Anime and Manga
Fairy Tail has Lucy, who ran away from home to get away from her overbearing father, whose thoughts were only about profit.
Sayako in Mahoraba lives in near poverty with her daughter. She makes plastic flowers and such for money and often needs help from Ryushi to complete whatever junk she and her daughter are making to survive. Their furniture and bedding are the cardboard boxes for shipping the flowers. Turns out she ran away from home to marry someone her father disapproved of. She comes from an extraordinarily wealthy family and she and her father appear to make up their differences though she continues to live with her daughter in poverty.
Konoka Konoe in Mahou Sensei Negima! is very rich, with only the fabulously wealthy Ayaka even coming close. Not that you'd ever know this by looking at her. Even her roommate was unaware until she actually visited Konoka's Big Fancy House. Even after the reveal, she never makes a big deal out of it, the only real mention of her wealth was when Jack Rakan nonchalantly billed her father 5,000,000 drachma for helping her friends.
Very late in the manga, it's revealed that Chizuru is also extremely wealthy, but like Konoka, she never makes mention of it or flaunts her wealth.
In the last episode of Chuunibyou Demo Koi ga Shitai!, Kumin mentions that Dekomori drove them. Cue them panning to a Mercedes-looking car with a stern looking MIB next to it.
Beelzebub. Himekawa is a variation: everyone knows he's rich, being the heir to a powerful family empire and all, just not to what extent. He's also not a Rich Bitch, considering he uses his cash to try and be the top delinquent at Ishiyama High, and does know how to fight, rather than stick with his friend and try to rule the country.
Kotobuki Tsumugi from K-On! is extremely sensitive about the fact that her family is filthy rich. She is unable to hide that fact completely, but she does her best to not draw attention to this.
Azumanga Daioh: Child Prodigy Chiyo skipped some grades and attends High School despite being of grade school age. She's so excited about being a highschooler she decided to get a part-time job because highschoolers usually have that sort of job. Her employer hired her because he thinks she must be poor to be desperate enough to "forge" a high schooler card. Since he never told her what he thinks, she's oblivious to the misunderstanding. She's actually wealthy.
Hans in Freaks. Even when we first meet him, it's clear that he's reasonably affluent, but when Cleo finds out exactly how wealthy he is, she decides to marry him. This goes poorly for everyone involved.
Mr. Miyagi in The Karate Kid. This guy starts out as a handyman, but we find out later that he owns oil wells and some nice property.
Matt Hooper from Jaws. Looks like an everyday working joe, but is actually the son of a rich New England family.
During the Bronze Age of Teen Titans, one would never guess that Changeling (Beast Boy) was heir to his adoptive father's estate - and Steve Dayton made Bruce Wayne look middle-class by comparison!
Weed in For Better or for Worse comes off as a fairly typical slacker college student, until he brings Michael with him on a visit home and turns out to be from an exceedingly wealthy family. He doesn't think much of it, because it's also a cold family.
Of all ponies, Pinkie Pie is revealed to be this in the Ask A Pony blog Slice of Life. Her father discovered high-quality rock molasses on his farm and became a millionaire from it, making Pinkie one of his heirs. Thanks to this, she was able to buy shares in Sugarcube Corner and keep it running (and able to live in the cupcake). To be fair though, it was never meant to be a secret. She just forgot to mention it. Also, consider she lives with the Cakes, works with them, and frequently foalsits their children. All because she's passionate about sweets.
In The Truth by Terry Pratchett, William DeWorde has had a falling out with his family and lives on around $50 a month, although since Discworld is a pastiche of Middle Ages/Renaissance fantasy, 50 Ankh-Morpork dollars ($AM) a month is a fair amount of money.
For comparison's sake, members of the Watch, the police force, make 30 dollars a month and are considered reasonably well paid.
William gets his income from various rich and powerful individuals outside Ankh-Morpork who pay him for writing to them about the general going-ons of the city. He figures out that the rich do not really want to see a member of their class live in poverty so they support him under this pretense. Only later does he realize how powerful what he does can be.
Susan Sto Helit is technically a Duchess, but has no patience for the job, and instead takes jobs like governess and school teacher. Her employers, a wealthy couple in their own right, were rather shocked to discover they one of their servants was more posh than them.
A minor Running Gag in Discworld is that the really rich can afford to act poor. Those who are only pretty rich will buy fancy clothes and jewelry and homes to try to make themselves seem much richer, but those who are supremely wealthy don't need to. Why buy new furniture when the stuff your grandparents bought was so good that it has lasted all these years? Why dress nicely when you don't need to work so you can devote all your time to messy hobbies like raising swamp dragons? And ironically, this allows them to stay rich. Sybil Ramkin is the best example, but Lady Margolotta and the Dowager Duchess of Quirm also qualify. And Sybil's husband Sam Vimes was born poor, but is now the richest man in the city. So naturally he prefers dented armor and cheap boots to the finery his station allows.
Except cigars. He likes the good cigars he can afford now that he's loaded.
In Percy Jackson and the Olympians, Rachel Elizabeth Dare is pretty much an enigma, but one time she walks up to a random chauffeur, says a few things, and suddenly he ditches his customer and takes the Olympians where they want to go. Turns out she's this trope.
From the sequel series, The Heroes of Olympus, we have Piper and Frank. Piper's classmates at her old school never caught on that her dad is a famous Hollywood movie star, while Frank's initial awkwardness and insecurity belie his family's old money.
In Fear Nothing and Seize The Night by Dean Koontz, Christopher Snow's best friend Bobby is this.
This genre convention was mocked in The Grapes of Wrath. Two Okies discuss a Broadway play about a rich man and a rich woman who pretend to be poor in order to find true love. The entire premise confuses the heck out of the second Okie, who doesn't understand why a rich person would screw out with such a ridiculous Zany Scheme. There's a depression going on, and the Okies are standing in line hoping to get work so they don't starve to death. The second Okie explains, very annoyed, that if he were rich he'd just sit in his penthouse eating steaks all day and he's incredulous that an actual rich person would do anything different.
In the Soviet/Russian novel The Little Golden Calf Alexander Koreiko is hiding his millions because he can't use his money in the Soviet Union and so he lives as a poor man (almost bordering on poverty), working on extremely low pay job, and basically all his posessions are two iron kettlebells to keep himself in good health — all to live for the day soviet regime falls. The book is set in 1920s...
Live Action TV
Hodgins from Bones, partly because he's a conspiracy theorist who thinks that old money, like his family, totally controls the world.
Considering how influential his family is as major supporters of the Jeffersonian Institute, he probably also hides his connections so he will be judged on his own merits.
He actually lives in a mansion, but since nobody from work ever visits him at home, nobody realizes that he has lots of money.
Averted over the course of the first two seasons as all the other major cast members find out about his wealth.
And finally no longer the case after serial killer Pelant forced him into a Sadistic Choice: shut down a computer server to keep Pelant from draining his accounts, or keep the server running in order to stop the military drone that would blow up a school in the Middle East. Hodgins doesn't hesitate to sacrifice his wealth to save the innocent lives.
Everyone is shocked when Dr. Carter from ER is revealed to be from a wealthy family.
In The O.C., Summer meets and is courted by "Che", a hippy student who claims to have "grown up on a reservation" and is generally very mellow and seemingly down-to-earth. After his final failed attempt to win Summer's heart, his chauffeur turns up to escort "Master Winchester" home.
Nick Knight from Forever Knight turned out to be this; in a subversion of Vampires Are Rich; the Vampire world discouraged it because it led to unfortunate questions that threatened the Masquerade if one's current role didn't match the funds they had. He was slowly and secretly giving it away.
In Boy Meets World Shawn is shocked to discover that Mr. Turner comes from big money and became a high school teacher after turning his back on his parents' wealth.
Hal from Malcolm in the Middle comes from a very wealthy family, but is estranged because his father was so eccentric and childish that Hal felt he was never a very good parent, while the rest of the family strongly disapproves of Hal's wife. Averted in that Hal and his family don't seem to receive any financial support from the family, despite their frequent money troubles.
Then it is revealed when Hal's father died that his father lost it all.
In one episode of The Suite Life of Zack and Cody, London Tipton pretended to be poor to date a man who hates rich people. However, when she had enough of the poor lifestyle, she confessed the truth and her boyfriend said he doesn't mind because she turned out to be nicer than he expected from rich people. She was just acting nice but didn't believe when people told him that.
The TV adaptation of The Dresden Files. Harry Dresden, as in the book series, lives in a small apartment without much in the way of amenities. However, here he is the sole surviving heir of Justin Morningway, Harry's uncle and an extremely wealthy and powerful wizard in his own right. Justin died after attacking Harry after Harry found out he had killed his father several years earlier. Both out of guilt and contempt, Harry has always refused to claim his inheritance, sticking to his apartment, refusing any money from his uncle's estate, and keeping Morningway's mansion in mothballs.
Sid Hammerback on CSI NY appears to be this at least in part. Jo knows about his success, and it's possible Mac knows, but no one else has given any indication of knowing it thus far. Although as of "Kill Screen", the piano in the morgue might have been a tipoff...
More of the team has found out, but he also gave a lot of his money away after learning he had cancer.
JAG: Bud Roberts is at first shocked upon realizing that his then-fiancée Harriet Sims comes from a wealthy family, when visiting her parents in Florida for the first time in "Yesterday’s Heroes".
Gary in Men Behaving Badly is revealed to scrimped and saved money over the years, to the point where he currently has a few thousand pounds in his bank account.
Raj Koothrappali in The Big Bang Theory. His friends know that his parents in India are well-off (his father is a gynecologist), but a later episode reveals that, in Sheldon's words, "They're not just rich. They're Richie Rich rich."
Ezra from Pretty Little Liars lives in a small apartment and works as a teacher, but his family is actually very wealthy
In one episode of Hogan's Heroes, Schultz revealed that he was the owner of the Schotze company, one of the oldest and most successful toy companies in Germany.
Dennis Farina's character Joe Fontana on Law & Order. There was even a B-story in which Detective Green notes that Fontana dresses in tailored suits, drives a $100,000 car, and lives in a penthouse condo and wonders how he can afford all that on a cop's salary. Turns out that Fontana's grandfather was the "original Chef Luigi" (a Bland-Name Product version of Chef Boyardee) and Fontana has been living on his share of the family fortune since he was a teenager.
Special Agent David Siegel, Neal Cafferey's new handler in Season 5 of White Collar. The moment they meet, Neal pegs him for this, which Siegel confirms when he says he can afford an apartment in a pricey part of New York (albeit not on his FBI salary), and that he has a yacht.
Slice of Life establishes Pinkie Pie as this, but it has no effect on the characters other than in a backstory flashback.
Samantha Manson of Danny Phantom is secretly rich, something even her two best friends didn't know for a long time. Every other rich kid at school is sort of a Jerkass, and as it is her parents' WASPish attitudes don't really mesh with her Perky Goth persona or Granola Girlactivism.