- Type A) Be dressed in an exaggerated, stereotypical version of what all today's hip young teens or kids are wearing.
- Type B) Fall back on cartoonish old classics such as beanies with propellers, Little Lord Fauntleroy outfits, sailor suits, and giant lollipops.
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Type A With Children Examples:
- Ephraim Kishon did this once in one of his stories (on Purim).
- Justified in Peter Pan in Scarlet—the now grown-up Wendy, John and the Lost Boys try on their kid's clothes, because doing so will make them young again.
- Early into The Mysterious Benedict Society Rhonda wore a green wig and a puffy white dress in order to pretend to be a preteen. She needed to a Secret Test of Character on the kids pretending to be another child. Her looks were meant to draw attention away from her age and distract the test takers in general.
- In the German comedy show Switch! Bernhard Hoëcker and Petra Nadolny do this regularly.
- The actress Shirley Henderson (born 1965) seems to specialize in this. Apart from her role in the Harry Potter films, she recently appeared in a TV production called 'May Contain Nuts' where she dressed as her 11-year old daughter in order to pass a test to get the girl into a good school. The ironic thing is that her character in Potter films, Myrtle, is actually older than her- but is a ghost, and thus still looks young.
- As part of the husband-and-wife comedy duo "The Krankies," Janette Tough made a career out of dressing up as a young boy to play "Wee Jimmy Krankie."
- The Simpsons: Homer tried this in "Hungry Hungry Homer" when he sneaked into Bart's class to try to get Sherri (one of the twins) to go out with Bart to the dance. Neither Krabappel nor the kids in the class pierced his disguise, and Homer managed to accomplish his goal.
- Also in an episode of King of the Hill where Dale attempts to apply for a job as paperboy for the Arlen Bystander (God knows why). He even uses the Totally Radical "jizzob" in place of the boring old "job." No one is fooled and Bobby instantly recognizes him.
- An episode of Recess had a government inspector masquerading as a kid, who was later found out when TJ overhears a buzzing noise in the school toilets and discovers him shaving.
- In the Wacky Races episode "Scout Scatter", the Ant Hill Mob fooled the sheriff by disguising themselves as Boy Scouts.
- In the nineties, some riot grrrl bands invented a style called kinderwhore. Courtney Love is the greatest example.
- Another musical example of this is AC/DC's Angus Young who wears a boy's school uniform.
- Youthful-looking adults can sometimes use this to enter Theme Parks for the children's price. For example, a woman hiding the shape of her body under overalls and a baggy T-shirt. The trick, of course, is not only looking like a kid, but remembering to act like one...
- One of China's "Twenty-Four Acts of Piety" was a 70-something old man pretending to dress and act like a toddler so that his 90-something parents wouldn't feel old.
- Back in the The Edwardian Era, one popular frock worn by little girls alongside sailor suits and Fauntleroy-style suits was the drop-waist dress◊. Flash forward to a couple of decades and the little girls had grown into fine young women, they had still worn the same silhouette.
Type B With Children Examples:
Anime and Manga
- The sailor suit/lollipop disguise was also employed by Bobnote Dalton from the Lucky Luke comic books, in a scenario involving robbing a bank with a revolver hidden in a piggy bank
- An Action Comics story from The Golden Age of Comic Books, titled "Fairlyland Isle", featured Lois Lane disguising herself as a little girl, wearing a sailor suit, Girlish Pigtails, and glasses. Details here.
- The Three Stooges short All the World's a Stooge. As part of a weird plot by a rich guy to get his wife to stop with her goofy philanthropic projects, the Stooges are adopted by the couple as refugee children. Moe and Curly get the sailor-suit treatment— and Larry is done up as a little girl with a big hair bow and pinafore.
- In V for Vendetta Evey dresses as a child prostitute to fool the minister as part of V's plan. It was made to be quite Uncanny Valley.
- Billy Wilder's The Major and the Minor, in which Ginger Rogers disguises herself as a minor in order to get a reduced train fare. Then she meets the Major. Hilarity Ensues...
- The sort-of remake You're Never Too Young has Jerry Lewis impersonating a child (with sailor suit) to elude mobster Raymond Burr and bother Dean Martin.
- In Trick 'r Treat, the guy Danielle has lined up to be Laurie's 'first' is an overweight guy dressed as a giant baby.
Live Action TV
- Not exactly a disguise, but one episode of Gilligan's Island had the Skipper regress back to childhood under hypnosis and he saw the other castaways as his old childhood playmates, dressed in old fashioned kiddie costumes.
- The Goodies did this when they were asked by the organizers of military style camp for children to find children for the camp. When they can't get any kids, they end up doing this.
- Also, in The New Office, they wanted to get the estate agent's sympathy, so Graeme dressed as an old worker, with Tim as his wife and Bill, with footed pajamas and oversized teddy bear, as his child.
- The Monkees take turns disguised as 11-13 year-olds in "Monkee vs. Machine", ultimately to throw a Spanner in the Works and disrupt a toy company's product testing session.
- Night Court had Dan's boss, the district attorney, try this to fool a suicidal children's show hero. Bonus points in that the adult is either a dwarf or a midget (I don't know which is the right term). It still fails, although the costume's used as a joke later in the show.
- That Mitchell and Webb Look featured a sketch detailing the origins of the Ku Klux Klan's uniform. In it, a tailor offers them the choice of looking scary by dressing up as pointy-headed ghosts or as little girls, because; "What could be scarier than a massive little girl?"
- The Abbott and Costello Show featured skits with Joe Besser as "Stinky", who would get into hilarious "Spoiled Brat vs. Manchild" spats with Costello.
- In the Saturday Night Live "Gilly" sketches, the title character's outfit flirts with this (the others are more modern).
- Vinny Vedecci's young son dresses as a sailor.
- The kids in El Chavo del ocho are all interpreted by adults.
- In I Love Lucy a pregnant Lucy is appalled at the thought of their child picking up Ricky's broken English. She declares that she will only allow perfect English to be spoken around her baby, and hires a tutor for both the Ricardos and the Mertzes. Fred Mertz takes this as "back to school" and comes to the first lesson dressed in an exaggeratedly childish outfit. Lampshaded by the tutor who notices Fred and Ethel both using the same hackneyed patterns and saying to Ethel, "You've corrupted your son here."
- One episode of The Drew Carey Show had both Mimi and Drew's then-girlfriend applying for a job in the cosmetics department, giving makeovers. One of Mimi's would-be clients was a petite, middle-aged woman who had been dressing in clothes from the children's department since childhood. Mimi lost it on her, and of course she didn't get the job.
- Tumbleweeds, a comical Western strip, featured outlaw Snake Eye and his little brother Snookie - ostensibly twelve, he looks like a malicious hulking grown man with stubble and a moustache, wearing the classic Little Lord Fauntleroy outfit.
- There was a Ren & Stimpy comic where an escaped zoo gorilla tried (and failed miserably, as Ren ended up Hanging A Lampshade on the whole thing by pointing out that "kids don't wear beanies") to blend into society by dressing up as a little kid. The tell-tale propeller beanie was indeed involved in the gorilla's disguise (the rest, if I remember correctly was just shorts and a t-shirt, but it's the beanie that was the important part).
- A sight gag in Futurama had an extreme closeup of the Professor's face as he says that luckily there are enough lifeboats on the Titanic (yes, it was a spoof of the movie) so no one would have to dress as women and children, with a Reveal Shot zooming out so we see that he's wearing a propeller beanie and holding a lollipop.
- Perpetual loser Oskar Kokoshka of Hey Arnold! used this sort of disguise, complete with a huge lollipop, in an attempt to infiltrate an audition for Yahoo Soda. It didn't work.
- An episode of Batman: The Animated Series called "The Laughing Fish" featured two of Joker's henchmen dressed as 1950s-era children (one with a beanie, one with Girlish Pigtails) for Joker's commercial for "Joker Fish" - and they did not enjoy it. Harley played their mom.
- This is also essentially the entire schtick of villain Baby Doll, who is a grown woman with the body of a young child due to a medical condition in a '50s-style saccharine sitcom (although, going by the episode's time frame, it would have been made in the '70s--the DCAU seems to have a generally different cultural and technical history from ours). Whenever she shows up in her childish clothing (including visible panties) it generally means she's up to no good.
- In a brief gag on The Marvelous Misadventures of Flapjack, a "little kid" (of the sailor suit variety to go with the show's nautical theme) asks to play a "bathroom game" with Flapjack. After Flapjack tells him, "You need to grow up," the "kid" then replies in a raspy voice, "Grow up? I'm 38 years old!" followed by a closeup of the middle aged man's face.
- The whole plot of another episode revolved around K'nuckles and Flapjack switching places to see whose life was harder. Throughout the episode, everyone mistook K'nuckles in his Flapjack costume for the real Flapjack and vice versa.
- Bugs Bunny's done this a few times. Sometimes all the way back, as it were.
- An episode of Goof Troop has Goofy going to school with Max in order to spend more time with him. He dresses in the typical sailor suit and everybody except Max and P.J. were fooled.
- A Hypocritical Humor example on The Simpsons had the Red Hot Chili Peppers performing "Give It Away" on Krusty the Clown's show in just their white underpants, leading Krusty to wonder "What could be more degrading?" - just before the camera pulls back to reveal him dressed in a sailor suit and curly blond wig and with a lollipop for the next sketch.
- Done in Lilo & Stitch: The Series in the episode "Sinker". Lilo, Jumba, Stitch, and Pleakly manage to stow away in a cruise liner to find the boat sinking experiment, Experiment #602, by dressing up as a family (with portly Mad Scientist alien Jumba dressing up as a child, complete with complete with propeller beanie, sailor suit, and giant lollipops, and 10-year old Lilo disguised as the adult).
- On the SpongeBob SquarePants episode "Pre-Hibernation Week", SpongeBob snowboards so fast he blows away a skier's clothes, revealing that he's wearing a sailor suit, a lollipop and riding a scooter. His mate looks at him puzzled.
"Uh, I can explain."
- In The Mask, a Running Gag involves the titular character briefly "transforming" into a cartoonish stereotypical kid, wearing a sailor suit and holding a giant lollipop, to mock his enemies. While he changes his body type, his face remains the same when he "transforms", so it would still count as a use of this trope. A very peculiar one, tough.
- Lolita Fashion is inspired by Victorian era children's clothing (which looked like shortened versions of adults' clothing).
- Specifically, the subcategory Sweet Lolita, with its emphasis on more childlike motifs and whites and pastels (as opposed to the darks and blacks of Gothic Lolita) is what gives the impression of this trope in play.
Type A With Teenagers Examples:
Anime and Manga
- In a rare example of adults not successfully "passing" as teenagers, the two homunculi from the Busou Renkin manga, Tai and Chi, attempt to pass themselves off as high-schoolers and fail miserably in their attempt. Not only are they obviously too old, but they end up looking completely ridiculous and deformed-looking (and one of them is trying to pass himself off as a girl, too).
- In a less serious context, Weda (and Ashio) in Haré+Guu definitely does not pass as "Wendy, 17 years old". Probably because everybody in the class immediately recognizes her as a mother of their classmate Haré.
- The whole premise of the movie Never Been Kissed, in which, amazingly everyone is fooled and believes that Drew Barrymore is in fact a teenager. Probably because the other teenagers were Dawson Cast as well.
- Spoofed in Not Another Teen Movie with an 80 year old in her place. Again: no one notices.
- Something very similar happens with the early Eva Longoria film Snitch'd, in which a man in his 30s goes back to high school, pretending to be a teenager. Again, everyone is fooled.
- This is also done in the 1987 movie Hiding Out. A stockbroker is testifying against a mob boss who was into some insider trading. There are death threats, so until the trial the stockbroker shaves off his beard, gives himself highlights and goes to high school. Once again, everyone is fooled, including his own family members.
Live Action TV
- Psych had an episode with one of these guys as the perp.
- CSI: NY had a darker version of this. It turns out that a teenage high school student who was accused of raping a fellow student was really in his 30s and his "father" was his similarly aged accomplice. They both gang-raped said girl and murdered a teacher in whom she confided. Unfortunately for them, their victim was the daughter of a minor character...
- In Strangers with Candy, a cop in his thirties tries to infiltrate the school drug trade, mostly by wearing a t-shirt and a backpack and badgering the students about weed. No one is taken in, although for some reason they never pass comment on the main character, a high school student in her forties who never even attempts to dress like a teenager.
- Law & Order had two cases that were both inspired by the one of Treva Throneberry.
- Law & Order: Special Victims Unit had a rather serious case, with a teenage girl who two boys literally fought to the death over... only it turned out she was in her late 20s, and had been passing as a high-schooler for years in an effort to reclaim the childhood she'd been denied. Then again, that meant she had to deal with a lot of statutory rape charges...
- The original Law & Order had a similar case where a woman was changing her name and resetting her age to 16, bringing statutory rape charges to block her attempted murder charge. the Investigation eventually revealed she had done thing at least four times and was actually at least 29!
- Appears in an episode of How I Met Your Mother when Lily and Robin attempt to infiltrate a high school prom in order to see a band perform. Despite Barney's advice on how to pass as "today's kids" (i.e. dress as sluttily as possible), they don't fool anyone.
- In Only Fools and Horses, Rodney Trotter has to pretend to be 14 years old to enjoy a Spanish holiday in "The Unlucky Winner Is...".
- 21 Jump Street, an 80's police drama, was about a group of young-looking narcotics officers assigned undercover in high school, led by none other than Johnny Depp. It was a vehicle for and one of the earliest examples of Dawson Casting. The Movie Lampshades the ridiculousness of the premise.
- In one episode of Friends Joey attempts to get an acting job playing a 19-year-old. He wears his underpants pulled high up over his jeans and a backwards cap, and tells Chandler, "Sup with the whack PlayStation SUP". Unsurprisingly, he does not fool anyone.
- 30 Rock: Steve Buscemi shows up as a private detective hired as a strike buster. A flashback shows his attempt to infiltrate a high school as one of the students. His ludicrous appearance has gone memetic.
- This was revealed to be the part of the MO of the killer in the "It Takes A Village" episode of Cold Case. The man's petite stature and childlike voice, coupled with wearing baggy jeans and sweatshirts enabled him to pass for a teenager, thus easily luring his victims away.
- NTSF:SD:SUV::: There's an episode where Trent and Piper go undercover in a high school to uncover a plot to blow up the school. Their disguise as teenagers is laughably unconvincing and hamfisted. At one point Trent runs into two other teenagers who are really an undercover magazine reporter and a guy from the future who is trying to ensure that his parents will conceive him.
- In The Non-Adventures of Wonderella, Dr. Shark jumps both age and species barriers by trying to dress as a human teenager.
- In the pilot episode of Clone High, Principal Scudworth and Mr. Butlertron try to sneak into JFK's party — dressed as completely outdated teenagers. Surprisingly, they fool no one.
- The toad licking episode of Family Guy where Peter goes undercover in Meg's school as teenager Lando Griffin, and not only fools everyone but becomes the most popular kid in school.
- And then later inverted in a different episode, when Stewie, the 1-year-old baby of the Griffin family, does pretty much the exact same thing as Peter.
- In Rockin' with Judy Jetson, George got arrested for doing this while looking for Judy.
- The magazine editor Val in Daria, though this was more because she ran her own magazine supposedly appealing to teens - and never stopped trying to act like one despite clearly being at least thirty. Most people weren't fooled, though they tended to suck up to her anyway.
- In Sym-Bionic Titan, One of General Steel's soldiers, Stevens, sneaks into Sherman High undercover, pretending to be a student. The fact that he's Older Than He Looks helps, but he still tries using outdated slang including quoting the "Wassssssssupp?!" commercial.
- The Simpsons: Mr. Burns once tried to convince the elementary school to sign over the rights to the recently discovered oil deposit beneath the school, by dressing as the teenage Jimbo and using what he thought was modern slang. Since nothing Burns does is ever modern, it's a wonder he even got the outfit right. Principal Skinner wasn't fooled.
Burns: (dressed as Jimbo) Well, me and my fourth form chums think it would be quite corking if you'd sign over your oil well to the local energy concern.
Skinner: Uh, Mr. Burns. (Burns gasps) It was naïve of you to think I'd mistake this town's most prominent 104-year-old man for one of my elementary school students.
- Truth in Television: At least two adults were convicted for fraud after being being caught after months of pretending to be high school students.
- Charles Daugherty aka Storme Shannon Aerison. A black man (born intersex and assigned the gender male) pretended to be a white teenage girl... and actually got a modeling job.
- Treva Throneberry, who used several aliases through almost 10 years. Each time she made herself pass as a teenage girl who was sexually abused and ran away from home, then threw tantrums when people started to suspect, and then disappeared.
- Either Internet predators or the FBI agents trying to catch them posing as teenagers.
- A lot of you know that one parent who tries to keep up with their teenage kids, or just never changed their teenage wardrobe after growing up.
- Sometimes cops or FBI agents will disguise themselves as teenagers to infiltrate a school so they can catch and charge teenagers who sell or use drugs.
- Dawson Casting is when an adult actor portrays a far younger character.
- Very common in cosplay, especially of the anime/manga variety. Many cosplayers are adults, and many popular anime characters are in their teens, leading to this trope; depending on the character, this can also fall into Type A with children or overlap with Wholesome Crossdresser. With the right makeup, it can be surprisingly effective.