Basically when wealthy people have trouble grasping concepts that are a way of life for people without money. These people have been spoiled all their lives, so they have had all these things taken care of for them. So when they try to do these things (by choice or not), they just don't get them.
Usually this is Played for Laughs, since it's a form of saying "Money can't buy common sense". Yet it can be Played for Drama, particularly if the character, through no choice of his own, lived in a Gilded Cage and so is not to blame. The situation is sometimes accentuated to the point of hilarity or tragedy when such a character suddenly goes broke and is forced to face the realities of working-class (or worse) existence. The Prince and Pauper often has the prince facing this problem.
Can overlap with:
Socialite (most instances are, if the character is a lady)
Upper-Class Wit (brilliant as they are, they tend to be severely deficient in common sense)
Upper-Class Twit (if this character doesn't really do much even by upper class standards)
Valley Girl (if this character is fashion conscious and inarticulate)
The boys of the Ouran High School Host Club can't grasp normal 'commoner' things like the supermarket. Haruhi, in the meantime, feels her blood pressure rising. Most of them love experimenting and experiencing 'commoner' things - especially Tamaki.
Nagi and Maria of Hayate the Combat Butler show this pretty well, though Maria is just Nagi's maid. When Hayate suggests using the subway, they're amazed. Nagi has gotten better about it due to Hayate's teaching.
When Hayate is asked to go away for three days, he's given a million yen (about $10,000) for living expenses. He tries to protest, saying he could live in the lap of luxury for a year with that kind of money. Maria asks him to not bring any of it back.
Which begs the question of what his idea of the lap of luxury is. It's a lot of money, to be sure, but it won't cover a full year's rent on a decent sized apartment.
Given that Hayate had spent about half his life being the primary breadwinner for his worthless and wasteful parents, just being away from them probably counts as luxurious.
On their trip through Greece, they use a helicopter. When Ayumu asks how expensive it is, Maria casually lists off a number in the billion yen figure.
In Sgt. Frog, Tamama's first experience with human houses is billionaire Momoka's. He is then reunited with Keroro at the Hinatas' home, and proceeds to ask where the maids are, what kind of stores are in the house... (along with detailed descriptions of his opulent lifestyle). Keroro is left seething with jealousy.
"Sometimes I break stuff just to watch them [the maids] run around." While Keroro is cleaning.
Particularly in the anime version, Kodachi Kuno of Ranma ½ could be seen as a rather dangerous variant of this trope — while she has the right background, she seems to be vaguely aware that the way she was brought up is not the way the world works. So she's determined to change the world to fit her views. This, then, is why she does stuff like cheat before fights or paralyze her potential love interests — she's so used to always having her way, to always winning, to always being the center of attention, that the possibility that things might not turn out this way drives her to overcompensation.
Pretty much every Noble in One Piece aside from a very few seem to think that anything can be done if they just throw enough money at it and have a high status. Also due to this they are morally bankrupt, and believe that the lower class are worthless trash due to the fact the lower class didn't "choose to be born noble".
Veronica Lodge of the Archie Comics doesn't know that camping should not involve telling your butler to bring you a first class dinner by helicopter to the woods.
Also, she seems to think that, because she has such immense wealth, she must never ever have a job of any sort, even if it's just to pass the time.
Veronica's twin, Lola, in the Cherry comic books. Very rich, yet prone to doing things like taking up witchcraft and having it backfire on her.
Film - Live-Action
In Mean Girls, Regina in a specific example. She could rattle off several mostly-illegal weight loss drugs (most of which either were expensive before being banned or would be expensive to ship from countries where they're still legal). Yet, she didn't know enough about health and nutrition to know whether or not butter is a carb.
Possibly just a commentary on how American teenage girls obsess over getting thin the fast and unhealthy way rather than via actual healthy living.
In Roman Holiday, Princess Ann gets so fed up with the demands and restrictions of royalty that she runs away and lives as a commoner for a day so she can experience "freedom." She's rather naive about a lot of things, particularly the fact that being a commoner has its own demands (such as actually having to work for a living).
Subverted and played straight in Coming to America. Akeem (Eddie Murphy) is actively trying to avert this trope after becoming disillusioned with his opulent lifestyle until then, cheerfully and determinedly struggling with living as a blue collar janitor at a local burger joint in order to woo Lisa into loving him for who he is. And he actually acclimatises quite well. It's actually his servant, Semmi (Arsenio Hall), who bitterly and reluctantly has to go along with all of this and complains about this manner of menial work and lifestyle being beneath him.
In Mel Brooks's Star Wars parody, Spaceballs, the bratty Princess Vespa doesn't fare as well as the two smugglers she falls in with when the three of them get stranded in the desert. As the leader of the group struggles across the sands moaning "Water....Water....", Vespa feels like she's dying because she doesn't have "Room service....Room service...."
Then there's the fact that she refuses to be rescued without her matched luggage, thought a hot-air hair drier was vital for traversing the desert, and the worst torment that can be inflicted on her is having her original nose restored after plastic surgery.
Her father also thought keeping her original nose from being restored was worth the death of his entire planet. He's not too bright either.
Grace in Dogville. Oooooh boy. And stubborn to boot.
Prince Edvard from The Prince And Me goes to an American college where no one recognizes him and he pretends to be a normal student. He actually keeps everyone from realizing who he is (until the tabloids find him) but his disguise is somewhat hurt by the butler who works for him in his dorm room.
Film - Animated
Princess Jasmine in Disney's Aladdin never had to deal with money, so she nearly got in horrible trouble when she left the palace.
Especially with the Islamic "eye for an eye" policy. Since she couldn't pay, that counted as thievery. And Islamic practice dictates that a thief get their hand cut off. Good thing Aladdin was there.
Scott Westerfeld's Leviathan has Alek, a sheltered rich sort-of-prince, who, when disguised as a commoner, doesn't even know how to pay for a newspaper.
Mary in The Secret Garden. She doesn't even know how to dress herself because "it was the custom" that she stood there like a doll and was dressed. Her gaining knowledge is rather helped by the maid not being a proper lady's maid who knows it's her job to brush hair and the like, so Mary has to do things an upper class lady would not normally have to do even in England.
While his precise age isn't given, it's implied that Kal Zakath of David Edding's Malloreon managed to reach his late thirties to forties without ever having learned how to shave. Belgarath points out how surprising it is that the emperor of a culture that breeds ambitious backstabbers regularly let someone other than himself hold a razor to his throat. Belgarion, on the other hand, takes it as an opportunity to establish a peership between himself and Zakath.
Michael Sevenson is the son of a wealthy baron on the Knight and Rogue Series, and even though he's been traveling and earning his own money for a year by the start of the books seems to have no ability to estimate the value on anything. Fisk often has to stop him from paying with the largest gold currency what's only worth the smallest brass coin.
As I stood in my lonely bedroom at the hotel, trying to tie my white tie myself, it struck me for the first time that there must be whole squads of chappies in the world who had to get along without a man to look after them. I'd always thought of Jeeves as a kind of natural phenomenon; but, by Jove! of course, when you come to think of it, there must be quite a lot of fellows who have to press their own clothes themselves and haven't got anybody to bring them tea in the morning, and so on. It was rather a solemn thought, don't you know. I mean to say, ever since then I've been able to appreciate the frightful privations the poor have to stick.
When Morgase Trakand goes undercover to escape being made a puppet, she turns out to be comically bad at pretending to be a maid (and humility in general), making her disguise flimsy at best.
British statesman Lord Chesterfield wrote about them in Letters to His Son: "He cannot withstand the charms of a toyshop; snuff-boxes, watches, heads of canes, etc., are his destruction. His servants and tradesmen conspire with his own indolence to cheat him; and, in a very little time, he is astonished, in the midst of all the ridiculous superfluities, to find himself in want of all the real comforts and necessaries of life." (letter 62)
Confucius related an example of this in one of his parables. A Self-Made Man's second son is put in prison, and he wants to send his third son to pay the bail; however, his first son insists on going. The first son bribes an influential man, who convinces the Emperor to open the jails...and then the son, not realizing the connection between the two events, thinks it's a coincidence and asks for the money back. The man returns the money, but then tells the Emperor to kill the second son before opening the jails so people don't think he's soft on crime. When he finds out, the father laughs because he anticipated this would happen; he wanted to send the third son (who grew up rich) because he didn't know the value of the money, while the first son (who grew up poor) would pinch every penny and get his brother killed.
London Tipton from The Suite Life of Zack and Cody, most notably in "Poor Little Rich Girl" in which her father loses all his money and she has to learn how to live like "normal" people.
On Cheers, Woody's rich girlfriend doesn't understand why Woody "refuses" to buy her expensive presents. If he doesn't have the money, why doesn't he just stop at an ATM?
Arthur from Merlin in the episode "The Once and Future Queen", when he's staying with Gwen. He says he'd like to take a bath, she tells him that might be hard as she doesn't own a bathtub, and he just stares at her, speechless.
Most of the Bluth family in Arrested Development, the point where, among the adults (if you could call them that), nobody but Michael and occasionally George understand the concept of work as anything other than an abstraction.
Lucille: You couldn't give Gob a banana? It's one banana! How much could it cost? Ten dollars? Michael: You've never even been inside a grocery store, have you?
Bianca Dupree of Beverly Hills Teens is forced to drive herself one episode, and she's horrible at it.
Shannon on LOST. She's painting her toenails and sunning on the beach while the others are trying to figure out how to survive on a deserted island.
Tracy Jordan from 30 Rock was likely poor in sense even before he got rich, but he's certainly no good with money now. He wears shirts made out of money and shoes made out of gold.
True to an absurd extent of Summer's family from Power Rangers RPM. They attempt to force their daughter into retirement from her job so that they can marry her off and get their wealth back as a dowry, despite her job being keeping the last human city on earth from being destroyed by killer robots.
In one episode of Night Court, Dan is forced to go on a date with a mob boss' plain-Jane daughter, and ends up connecting with her on a deep emotional level. But her father doesn't want them getting deeply involved, so he threatens to cut her off if she doesn't break up with him. She reluctantly agrees, explaining that she's lived such a sheltered life that she doesn't know how to live without her father's support—she once got mad him and ran away to her summer home, where she nearly starved to death because she couldn't figure out how to use a can opener.
There was a Reality TV show where millionaires went to live with lower-income folks for a week/month/whatever, that seemed to use this as part of the premise.
The show Undercover Boss features the owner/CEO/president of a large corporation working anonymously (with a cover story given as to why a camera crew is following this person around) at an entry-level jobs within the corporation. It's fairly common for them to be really bad at it. The premiere episode actually featured the president of the company being fired (in his fake identity) by his supervisor for being so inept at his job...of cleaning out Porta-Potties.
Stingy from LazyTown has trouble functioning in regular life because he wants to own everything he sees.
Rachel Greene from Friends is a mild example of the trope. She was raised in a wealthy family and was set to be married to someone, but she wound up running out on her wedding and crashing at her not-so-rich-friend Monica's apartment. For a long time, Rachel had to learn how to do things that were autonomous to everyone else, such as taking out the garbage and serving drinks to people in a cafe. She does get better in the later seasons.
Rachel later tries to extend the same help to one of her sisters, and it fails spectacularly, although in her case she wasn't just sheltered, but remarkably stupid, to the point where she doesn't understand why her attempted baby salon business (which consists mostly of her telling parents that their babies are ugly) is failing.
Inverted in the Beverly Hillbillies. A group of poor country folks become ungodly rich by finding oil on their land, and half of the humor of the show is them applying their extreme practical ideas, from long experiences of being dirt poor, to the luxuries of the rich.
The Carrington sisters in Elite Beat Agents don't know how to eat bananas; they're too used to French or Italian food.
Mitsuru Kirijo, the Ojou of Persona 3, is at a loss as to how to function in a fast food restaurant and (in a classic case of situational irony) is unable to buy food at a vendor's stand because it doesn't accept credit cards.
Luke Fon Fabre of Tales of the Abyss starts out like this, as an effect of his Laser-Guided Amnesia and the fact that ever since he lost his memory, he hasn't been allowed outside his parents' manor. As a result, he doesn't even know how to buy things at a shop.
Cave Johnson of Portal 2 fame owned Aperture Science, a major research corporation, and it is implied that he was at a time astoundingly rich. However, his own issues (such as the obsessive development of the Portal Gun and his original job, selling shower curtains) and idiotic financial decisions (or marketing Mobility Gels as pudding, compulsively buying moon rocks while his company was in financial straits) led to his downfall and may have contributed to his insanity.
Two of the "core tenets" of Aperture, the Heimlich Counter-Maneuver and the Take-a-Wish Foundation, couldn't have helped, either.
In Drowtales, when the drow search party reaches the surface:
It's played straight with The Ojou, Ariel, who gets agoraphobia (fear of open spaces), and Liriel, her pampered slave, who doesn't know grass =/= "weed". Ironically in Liriel's case she's actually from the surface originally, being Diva'ratrika, the former empress, through a Fusion Dance, not that she knows this at the time.
Subverted in that Kyo, probably the wealthiest member of the group, has been to the surface before and likes it.
As you would expect, Not Always Right is full of stories about customers trying to weasel their way into getting a discount. However, on the other end of the spectrum there are just as many extremely stubborn customers who will pay the price posted and only the price posted, no matter what sales or discounts are in effect despite not being advertised. It's like they're hardwired to believe that no matter what the store workers do, they're trying to rip them off.
Phase/Ayla Goodkind from the Whateley Universe, raised in a super rich but sadly mutant-phobic family and only fully realizing just how good he had had it when disowned by them and left to fend for himself upon manifesting. Played sympathetically, though, as he's deliberately doing his best to adapt and where possible even improve conditions for others. ("Goodkinds don't complain, they fix things.") It helps that even with the "pittance" his family begrudgingly paid him to go away and keep quiet he's still one of the richest and most finance-savvy students on campus; does have to use the same facilities as everybody else, though...
A sketch on an October episode of The Brian And Jill Show featured Jill Whelan as Contessa Bitsy Cargengie Worthington. A Blues singer who, due to being wealthy, had a very different idea of what the blues actually were.
My jet pilot got the gout... aaaannnnd his doctor won't let him fly. Ohhhhhh yeah. So I'm forced to fly commercial... I might as well lay me down and diiiieeee. I'd say flyin' first class is for peasants! And I'd rather stick needles in my eyyyyyyeeeee.
Pops from Regular Show. He was raised in a wealthy, isolated way, resulting in him having a child-like fascination with EVERYTHING. He's an old man who acts like a very young child due to his naivety. But this is also partially due to him being from another land entirely.
It's implied that he was much more mature and lucid when he was younger, but then Mordecai and Rigby accidentally ran his past self over with a gold cart, possibly resulting in his childish personality.
The Earl of Lemongrab of Adventure Time is a presumably rich heir of royal blood... but he's exceedingly sheltered and relies on his servants for basic things such as having food prepared for him.
Mr. Pewterschmidt from Family Guy turns out to be like this when he temporarily loses his fortune. He can't even go to the bathroom properly.
Lois: Dad, when you went to the bathroom earlier today...did you wipe?
Mr. Pewterschmidt: Nah, I used to have a guy that did that for me.
Token: I'm just so happy you guys moved into town. You see, I used to be the only rich kid. All the other families here are kinda low to middle-income.
Lisa: Why? What happened to all their money?
Token: Well, they never really had any money.
Lisa: Well, then, why don't their daddies just act in a movie?
On the Animaniacs, the Hip Hippos tried to do all their own chores when their maid quit, and failed miserably.
There was also an episode where the CEO's secretary has to go home sick. She tells him to call a temp. Hilarity Ensues when he struggles with that chore.... and ends up calling the Warner Brothers instead.
A dangerous example happened in Batman: The Animated Series. After the Penguin was released from prison, a wealthy socialite, on urging from her friend, pretended to have a crush on him, both of them thinking that associating with him would be good PR. The Penguin was actually happy for a while, and was considering giving up crime... Until he realized he was being used. At that point, he kidnapped the socialite, and tried to kill her friend when he delivered the ransom. Once Batman had apprehended him, she felt a little sorry for it all and tried to apologize... To which the Penguin responded, "I guess it's true what they say, society is to blame... High society..."
Dethklok had trouble shopping at supermarket, or "food library", as they thought it was called. In fact, most episodes are about them trying to do things outside their comfort zone. This despite the fact that their music isn't exactly the kind clueless rich people would play. In Tributeklok it's suggested that they forgot how to live like poor people because being poor is awful, right before they blow off a tribute gig to go back to eating expensive gourmet food.
Mr. Burns from The Simpsons was lost in the "real world" when he lost his fortune.
Mr. Burns: Ketchup... catsup... ketchup... catsup... I'm in over my head here.
There is also the time that he started to do things on his own. Hilarity Ensues
Mr. Burns subverts this trope once when he's attacked by Homer after Homer is put in charge when Smithers left on vacation (Smithers expected Homer to do such a terrible job that Mr. Burns would be glad to have him back on his return). Things go horribly right and Mr. Burns is so terrified of Homer that he's forced to learn to do things on his own resulting in him firing Smithers for not needing help anymore.
The Bluff family from Doug seems to have this problem in spades. In one episode, Mr. Bluff is trying to "inspire" Doug with the story of how he started his bumper sticker business all by himself before he remembered he was filthy rich and hired people to do all the hard work for him. In another, Beebe needs to have the meaning of "broke" explained to her.
Rhonda from Hey Arnold! also had to learn how to live poor after becoming such.
Adonis from Hercules: The Animated Series. In one episode, he accidentally had Hercules trapped in holding up the sky (Greek Mythology) and Atlas was ready to leave him there. Realising he couldn't bribe Atlas into taking back the burden, the only thing he could think of was tricking the god into temporarily holding the sky so Hercules could give back Adonis' purse.
Thanks to a classic Merrie Melodies cartoon, we know not even pet heirs are immune to this trope. In "Aristo-Cat", when a rich cat's butler quit, the cat had no idea of how to feed himself. He thought about eating mice but this plan was halted by the fact he had no clue to what a mouse looked like. One even tricked him into thinking a dog was a mouse.
DuckTales: Scrooge almost married an already wealthy Gold Digger whose idea of wilderness was a hotel with no beauty salon.
A Pup Named Scooby-Doo 's incarnation of Daphne, who would randomly call her butler Jenkins in to do things for her, such as being scared. (Not that she couldn't have done so herself, but a Wild Take in the style of the other characters might have mussed up her hair.)
In contrast, Scooby-Doo! Mystery Incorporated has everyone in the Blake family but Daphne being like this. Her dad once bought a car just to have it sit around their living room as a decoration.
Daphe's mother: Only need a little [money]? Where did I go wrong with her?
Amy: Don't worry mom. You can always come live with me.
Mrs. Wong: No we can't! Who do you think been paying your rent!?
Amy:(clueless smile) What's rent?
Seņor Senior Junior in Kim Possible is a wealthy fop, who we first meet tanning under a sun lamp the size of a blimp. His father's decision to take up supervillainy as a hobby could be seen as another example, though he otherwise seems to have as much common sense as anyone.
In one episode, Ron suddenly receives millions of dollars in royalties for inventing the "naco". He spends much of the episode squandering the money on bling and frivolities until Drakken and Shego steal what's left (after which they blow it on another failed attempt to take over the world).
More than one lottery winner has been burned by this trope. Some have no idea how to manage all their money and blow it all in record time. Others end up getting conned or even just robbed of their newfound wealth.
The Dutch national lottery actually offers counseling and an trusted accountant to prevent this trope from occurring.
Similarly, this trope tends to befall professional athletes, with Mike Tyson being a poster-boy for his excesses (various mansions around the country, etc.).
The concept of Conspicuous Consumption was first coined by Norwegian-American economist Thorstein Veblen in his book Theory of the Leisure Class This book defines the Leisure Class as this trope: People whose only duty is to spend money whitout any other real reason that to show they can afford it. Jorge Luis Borges resumes: