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Boyish Shorts

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Boys don't wear long pants. At least, not in media.
This trope is when a preteen boy is almost always depicted wearing shorts—short, often plain in design pants that don't go below the wearer's knee.
The shorts help visually direct the boy as significantly younger than the older men (and sometimes teenage boys) around them, who are almost always depicted in ankle-length pants. It's that at the core, but it also helps show the boy as more active, free, childish, or immature than said adults. It may also show the boy as more naive, hopeful, joyful, cheerful, and/or playful than others around them. Or just of lower social status, with them being seen as a child easily by the mode of their dress.
Three traits need to exist for this trope to apply to the character, so it's not just boys wearing shorts:
The shorts are, well, short. Knee length at most. They aren't very far past the knee but can be as high as mid-thigh for very young children. Calf length or capri length isn't short enough. Knickerbockers and shortalls (short overalls) count, but plus-fours are too long.
The person wearing them is a prepubescent boy. At most, he's early into the teenage years—generally no older than fourteen. Once he's in high school (or the equivalent), it's just clothing he's wearing (unless he's trying specifically to evoke youth or childishness by wearing said shorts). Also, it's only boys that get this trope. Girls in shorts, regardless of their youth, are seen more as Tomboys unless they're wearing them as Modesty Shorts—or if older, they come off as a Ms. Fanservice if they're super short and thus intended to be sexy.
The shorts are an important part of the character's characterization/appearance, in part to direct him visually as being young, childish, and/or immature compared to the pants-wearing adults around him. It needs to be important he have on shorts, even if the importance is just "this character is less mature" or "this is a young boy among adults" instead of just wearing them to look cool or as a general article of clothing.
The last one is the hitch: shorts ought to be so much part of the boy's look to the point he's rarely depicted wearing anything else. Adult men wear shorts sometimes—say when on vacation, at the beach, or in the summer—but a boy in Boyish Shorts wears them practically all the time. The rare times this boy is wearing pants, it's either due to the weather (such as winter wear), a temporary costume change, or as a visual sign they're attempting to be, are, or appear more mature than their age. Pants make him more stuffy, mature, world-weary, and/or "grown-up" compared to the immaturity, youth, lack of responsibility, and freedom afforded a boy. This also includes cases of adult characters being aged down; they're frequently put in short pants to indicate they're now—even if temporarily—children.
The shorts can either be perceived as upper class or middle/lower class, depending on what footwear and tops they're paired with. If the shorts are paired with knee socks and buckled/dress shoes, this is a more posh, upper-class look (especially if a nice blazer or sweater vest is included); if paired with sneakers and a t-shirt, it's an active, childish, often mischievous/troublemaker look.
This is Truth in Television as historically it was considered lower class to dress a boy in long pants before a certain age—or if the boy decided on wearing the long pants himself, acting above one's age. Until the late 19th century, upper and middle-class boys often wore dresses the same as girls from birth until they were three or four years old, about the time he was potty-trained. He was then breeched (put in his first pair of short pants), thus separated from the girls and mother socially in appearance. He then mostly wore short pants until he was considered mature enough to wear long pants regularly, generally about age twelve or thirteen. When the dresses stage was replaced with rompers, they were still followed by shorts. The shorts and kneesocks look didn't take off as much in the US during the era they did in England—the 1920s and 1930s—but did among the upper posh or preppy classes, and in the US it was often instead knickerbockers paired with high socks.
Shorts are also more practical in eras where new clothing took some time to procure, so outgrown clothing couldn't be easily or quickly replaced. Even post-industrial revolution, when clothes could be replaced slightly more quickly, parents often used hand-me-downs to not have to buy tons of clothes for multiple children growing fast. Kids tend to grow long in the limbs before they grow out or up in the torso; thus, shorts can look fine on rapidly growing children regardless of their length whereas pants could look too short after a big growth spurt and expose ankles and socks—and thus have to be either continuously maintained or replaced to avoid the "highwater" look. Shorts are also a visual gender division from an early age since the mid-20th century, letting gender-concerned parents worry less that their baby boy might be mistaken for a girl if dressed androgynously.
A Sub-Trope of Clothing Reflects Personality and Meaningful Appearance. Often seen on the Bratty Half-Pint or Kiddie Kid. An adult man or teenage boy hit by the Fountain of Youth might find himself in these, or an older character during A Minor Kidroduction. Combine these with Rough Overalls and you get the shortalls version of Kiddy Coveralls (which itself is an article of clothing that shows a young age). Has nothing to do with Boyish Short Hair.
Note: All examples must explain why the shorts matter to the character or image of the boy wearing them and/or state that the shorts are tied to a representation of his youth, not just state that he has them on or else it's People Sit on Chairs.
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Story of Seasons (2014) has villager Lutz in the more preppy version (minus a set of somewhat practical boots), and the boy twin in these as the more active version with farm boots. Since none of the children get older or ever change clothes, they always wear them.
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Genshin Impact: There are two male body types in the game: teen and adult. The adult ones all wear pants but almost every teen one is depicted in shorts to show they're younger.
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Zigzagged with Astro Boy, who's a young, learning about the world robot. While his school uniform does indeed contain shorts, his iconic design (which has black trunks) is literally painted onto his metallic skin, meaning he's technically naked most of the time.
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Detective Conan: Young Conan's Iconic Outfit mostly resembles the high school uniform he wore before being turned into a child—but as a child, the necktie's replaced by a bowtie, the dress shoes with sneakers, and the long school pants replaced by a pair of shorts.
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The younger male Player character of Let's Go Pikachu/Eevee, Chase, wear shorts—in contrast to the older Red and Blue's wearing pants, who are being shown as skilled trainers compared to newcomer Chase.
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The Simpsons: Bart Simpson is close to the Trope Codifier. He (as well as a good many boys in Springfield Elementary School) are seen in knee-length shorts as part of their default look, in contrast to the pants-wearing men around them—including their adult nemesis Principal Skinner. The times Bart specifically wears pants are few and far between, often for just the episode, and if it's not because of winter it's him appearing more mature (such as his white preacher suit in "Faith Off").
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A 1980s-era Garfield strip had Jon's father tell him that his brother Doc Boy hates to be called "boy" ever since he started wearing long pants—the joke being that Doc Boy only just started wearing long pants the previous week.
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King of the Hill: Bobby Hill through the whole series rarely wears anything but short pants, as he calls them—and often shows a lack of knowledge and naivete, and is easily manipulated or persuaded into getting himself into scrapes his father has to remediate. Even as he gets older and more thoughtful compared to past him, he's still less mature than his father Hank who is almost never seen in anything but pants. The same is true with his best friend Joseph Gribble, even after puberty takes hold and he shoots up in height—his desperate desire to be involved with girls and see Luann naked marks him as no more mature emotionally than Bobby.
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In The Music Man, one of the signs of corruption that Harold Hill uses to rile up the citizens of River City into moral panic during "Ya Got Trouble" is asking the parents if they've noticed their sons re-buckling [their] knickerbockers below the knee because of the pool hall in town. The shorter knee-length knickerbocker pants are a sign of the boys still being in childhood, and the boys trying to wear them longer is a case of them trying to pass themselves off as older than they are (clearly, to get into said local pool hall).
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Leave It to Beaver has one episode where June's aunt Martha watches the boys while their parents are out of town. She takes Beaver shopping for a "proper" suit, which includes short pants as she thinks this is what boys his age should be wearing. Beaver is, of course, humiliated when she makes him wear the suit to school.
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Ken Amada, of Persona 3, is the youngest (human) member of SEES, and all of his outfits feature very short shorts, including his school uniform and winter clothes. When a now teenaged Ken shows up in Persona 4: Arena Ultimax, he has traded in the shorts for proper pants.
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Robin wore green shorts as part of his superhero uniform which emphasized him as the "Boy Wonder" and Kid Sidekick to Batman; his outfit had shorts from the 1940s through the 1980s.
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Milo Murphy's Law: 13-year-old Milo Murphy is shown wearing greyish-brown, knee-length shorts as part of his usual attire. This helps to emphasize his friendly, cheerful personality, and his optimistic outlook on life even when he's faced with misfortune.
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Caillou wears blue shorts, is a young child, and is known for his bratty and immature personality.
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Doraemon: Shorts are the go-to wear for the two young boys: Nobita (reflecting the wimpier, foolish, childlike side of shorts) and well-off Sueno (reflecting the wealthy upper-class representation of them). They're both in contrast to neighborhood jerk Gian who usually wears long pants.
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Arthur averts this trope with the older boy characters, including the title character. It plays this trope straight with the Tibble twins, who are DW's age (approximately preschool age) and known for their mischievous and troublesome personalities.
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Batman:
When Batman was transformed into Bat-Baby, he was placed in short-legged overalls◊, so this overlaps with Kiddy Coveralls.
Robin wore green shorts as part of his superhero uniform which emphasized him as the "Boy Wonder" and Kid Sidekick to Batman; his outfit had shorts from the 1940s through the 1980s.
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Phineas and Ferb: Phineas—who is at most ten years old—is always depicted wearing shorts, except in the winter—meanwhile, his quiet, stoic stepbrother Ferb is shown wearing rolled-up pants. In addition, when Phineas builds something, sometimes the person delivering the materials will comment on how young he is to be building it. In contrast, the adult male characters Dr. Doofenshmirtz and Lawrence Fletcher are almost always seen wearing long pants.
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Barbie:
Ten-year-old Todd—in both the 1960s as Tutti's twin and the 1990s as Stacey's—wore shorts in many of his individual releases; this helped show him as younger than the mature adult male dolls like Ken. (He had pants in the first 1990s release, but this is part of the "cool look" and he came with soccer shorts.)
Ricky, a short-lived friend of Skipper, came in a beach shirt and shorts.
Boy members of the Kelly Club, such as Tommy (Ken's younger brother) and Ryan, almost always came in knee-length shorts, showing them as preschoolers and thus even younger and more childlike than Todd. This is also true with the aged-up early-elementary boys that are now part of Chelsea's line.
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Toy Story: Andy Davis, at least before hitting puberty, wore shorts, and is a kind, young boy who really loves playing with his toys.
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In Malèna, twelve-year-old Renato angsts that he's the only one amongst his friends who still wears short pants; his father doesn't get him long pants until after he's matured and Il Duce (Mussolini) is dead.
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Gigantor: Shotaro Kaneda's Limited Wardrobe combines shorts with a button-up jacket, reflecting both his youthful nature and seriousness towards protecting Japan with his giant robot. Said outfit was passed onto Daisaku Kusama, another Yokoyama creation, for the Giant Robo OVA a few decades later.
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Wagons West: Set in the early 1890s. Toby's son Mike, who wants to marry Eden when both finally turn 18 but has a history of a bad heart, asks a doctor if he could one day marry. The doctor answers with shock in his voice and reminds Mike he just got out of "short pants", and it's too soon to think about such things at his age.note The answer is "yes", but he runs the risk of turning Eden into a young widow.
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Hilda: David (who is in the same class as Hilda and confirmed to be 11 years old in seasons 1 and 2) nearly always wears shorts—regardless of whether he is wearing his regular clothes, his Sparrow Scouts uniform or his school uniform. The only times he is seen wearing long pants are when it's snowing. And—while not necessarily immature—he is easily the least brave of the three main kid characters, with many of the creatures they encounter frightening him.
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Odd Squad has some agents-in-training sport a pair of navy shorts as a contrast to the navy pants that the more experienced Investigation agents—as well as agents in other departments like Science—wear.
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Pokémon:
The Youngster Class of trainers (called Shorts Youngsters in Japan), which are always boys younger than the player character, wear shorts and almost always battle with early-game Com Mons such as Rattata or Pidgey. This shows they're still beginner trainers who aren't too skilled compared to later more challenging trainers like Ace Trainers, Sailors, or Gym Leaders. (In Red and Blue their wearing shorts is directly noted by a Youngster on Kanto Route 3 — named Ben in the FRLG remakes — who says before he fights that he likes shorts because they're comfy and easy to wear—a line so unique it became memetic in the fandom.) Other classes of early or easy male trainers also wear shorts in this way. Bug Catchers, another early game trainer specializing in Bug Pokémon, all wear shorts and are young. Campers (previously called Boy Scouts) only wear shorts and are younger than the player character and more active, specializing in Pokémon found in the woods. Initially Schoolboys in the first two generations were pictured in shorts to make them appear as young kids in the early grades of school but later were aged up and put instead into full pants—showing they're older than the aforementioned Youngsters and the added Preschoolers (who are also in shorts), even if not adults compared to other trainers.
The younger male Player character of Let's Go Pikachu/Eevee, Chase, wear shorts—in contrast to the older Red and Blue's wearing pants, who are being shown as skilled trainers compared to newcomer Chase.
Bugsy, considered one of the youngest Gym Leaders, wears shorts like Bug Catchers.
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Rugrats: Chuckie, a toddler that's more dressed and slightly older than the other babies, wears shorts in contrast with the adult men around him including his father.
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Futurama:
Cubert, Professor Farnsworth's clone son, is almost always pictured in shorts, and is much younger than his genetic parent. This is also true with Hermes Conrad's son Dwight, which is both showcasing his youth and the implied relaxed attitude of their Jamaican background.
In "Teenage Mutant Leela's Hurdles", this is mostly averted with the aged down crew; Fry and Hermes are mostly shown in long pants. However, Hermes is briefly shown in shorts with a sailor top when they're small kids, Fry wears Kiddy Coveralls on the way to the Fountain of Aging as a toddler, and young Professor Farnsworth wears shorts with a button shirt and bow, high socks, and black shoes in the more nerdy/old-fashioned style at the fountain (before briefly returning to pants before he goes in the fountain with the infant rest of the crew).
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The Giver: Invoked by the community. Boys in the highly structured community are not given long trousers to wear until they reach the Ceremony of Eleven (individual birthdays are not celebrated, so their age cohorts celebrate milestones as a group), a symbol of their immature age status and childhood in the Community. Wearing long pants is a right of passage for boys leading them closer to their adulthood, with the children all receiving their adult role assignments the next year. Jonas is already near 12 at the start of the novel and so he has already graduated to long-pants status.
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When the Muppet characters were seen as babies in Muppet Babies (1984)note and first seen in the "I'm Gonna Always Love You" sequence from The Muppets Take Manhattan, the male characters that normally wear full pants like Gonzo and Scooter were instead put in short pants or romper style clothes, in contrast to their adult appearance. And while Kermit isn't often dressed at all with just his collar and Fozzie just wears a hat and tie, Baby Kermit wears a sailor suit with shorts while Fozzie is decked out in a short yellow romper set. This is also true in Muppet Babies (2018) for Kermit and Fozzie still, though Gonzo has been updated to wear Kiddy Coveralls.
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Peanuts has—outside of winter settings—the boys such as Charlie Brown, Linus, and Schroeder wear shorts. While adults aren't seen, the shorts help visualize the children as young—too young to wear pants regularly—and thus still naive and young. Averted with Franklin who wears long pants, but he wasn't introduced until the late 1960s when the idea of long pants was becoming more common on young boys.
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Boyish Shorts
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SpongeBob SquarePants: Inverted and invoked in the episode "SpongeBob LongPants". SpongeBob, who almost always wears short pants, switches them out for long pants. He starts to be perceived as mature and elegant in the longer pants; Patrick calls him a "man", and SpongeBob even passes his driver's license test due to wearing long pants. This is in contrast to his otherwise regular childish behaviour.
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All three lead protagonists of the Mother series (AKA Earth Bound) are young boys wearing shorts, though this is more visible on their clay models and Ness and Lucas' Super Smash Bros. models than in pixel art. They're all young boys who are thrust into saving the world unexpectedly but retain their boyish cheerfulness despite their skills and travels.
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Boyish Shorts
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Winnie the Pooh: Christopher Robin is always drawn in shorts (even when the buckle shoes from the 1920s were updated to sneakers), which characterises him as a six-year-old boy who still engages deeply in imaginative play with the creatures of the Hundred Acre Wood (who are his stuffed animals).
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Naive, imaginative Doug of Doug, along with his free-wheeling best friend Skeeter, are almost always seen in knee-length pants. Averted with Roger, who wears long jeans all the time.
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Gravity Falls: Dipper Pines wears short grey pants; he's actively running around the woods and also younger and more immature than teens and other characters that he comes in conflict with. This puts him in contrast with deceptive, conniving Gideon Gleeful (who is certainly not childlike) and aloof teenage Robbie who sees him as a child tagging along with the teens.
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The following is a list of statements referring to the current page from other pages.

 Boyish Shorts
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Always Male
 Boyish Shorts
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Immaturity Tropes
 Boyish Shorts
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Tropes in Pants
 Boyish Shorts
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Youngsters
 Peanuts (Comic Strip) / int_f6fd23ae
type
Boyish Shorts
 Malèna / int_f6fd23ae
type
Boyish Shorts
 The Giver / int_f6fd23ae
type
Boyish Shorts
 The Music Man (Theatre) / int_f6fd23ae
type
Boyish Shorts
 Muppet Babies (1984) / int_f6fd23ae
type
Boyish Shorts
 Muppet Babies (2018)
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Boyish Shorts