We've all seen people wearing the wrong clothes— like Adults Dressed as Children, or wearing a swimsuit to work— but wearing the right clothes, but on the wrong body parts, is even more hilarious, and that's where this trope comes in!
Quite often it's a little kid doing it to highlight how goofy little kids can be, and a common move for fictional toddlers is putting their pants, undies, or diaper on their head.
Maybe the joke is that a character is so dumb or naive they don't know which garment goes where (e.g. a character tries putting their socks over their shoes).
They might also be doing something goofy to make a small child laugh/stop crying/fall asleep.
Another variant is seen in Edutainment Shows, meant to teach kids to get dressed (e.g. "Does this go on your hand? No! Does it go on your foot? No!").
Sometimes seen in parodies of Underwear of Power with characters playing superhero by actually wearing underwear over their pants. Improvised Diaper can overlap with this if the baby is wearing another piece of clothing as a diaper. Compare Dressed in Layers for clothes worn under other clothes.
- The Pull-Ups website has an article on how to introduce the eponymous training pants to your kid and suggests saying, "Do we put them on our heads? Noo! Do we put them on our elbows? Noo!".
- Yotsuba&!: Yotsuba's father will occasionally entertain her by throwing a pair of shorts on his head and declaring himself "Boxerman".
"Which way is up? Which way is down? I do not know!"
- In one Calvin and Hobbes strip, Calvin attempts to head out for school with his shirt and pants swapped, so he's wearing his shirt as pants and has his pants on his arms. His mom is not amused, and makes him go change.
- Dilbert: One early strip (back during the George H.W. Bush administration) has Dogbert comment that the U.S. President is still a normal guy: "He puts his pants on one leg at a time, just like the rest of us." The final panel shows the President not just wearing his pants on his head, but trying to shove his upper body into one leg. His wife facepalms and thinks, Not again...
- In a Peanuts strip from September 1985, Lucy tells Linus that she intends to try out for the girls' basketball team. She tells him one thing she's learned: "You don't put the kneepads on over your head."
- In the My Little Pony: Friendship Is Magic fanfiction Pound and Pumpkin Cake's Adventures (and Misadventures) in Potty Training, when Sweetie Belle babysits the Cake twins, they put a pull-up on her head.
- Exploited in Bee Movie when Ken puts winter boots on his hands to try and kill Barry with.
- In Fantastic Mr. Fox, Ash wants a bandit hat like Mr. Fox, Kylie, and Kristofferson, so he cuts eye-holes in a tube sock and wears that on his face.
- In Inside Out, Riley's "Goofball Island" was established when she was running around after a bath as a toddler wearing only a pair of underwear, which was on her head.
- The Absentminded Fellow by Samuel Marshak has the Establishing Character Moment for the titular character being him putting his arms through the sleeves of the shirt - before realizing these are actually pants.
- Animorphs: In book #4, as Ax morphs into a human for the first time, the others realize he'll soon be naked and turn around, pointing him toward some clothes. When they turn back to him, he's pulled the T-shirt on like pants and the boxers are on his head.
- In "Babysitting Mode", a book based on Incredibles 2, Edna Mode is tasked with babysitting Jack-Jack. At one point in the book, Jack-Jack fashions a superhero costume from bits and pieces of the supersuits Edna designed, which includes wearing a sweater as a cape. Edna disapproves of this, which in turn, angers Jack-Jack, turning him into a monster that Edna now has to calm down.
- In the children's book Blue Hat, Green Hat by Sandra Boynton the turkey repeatedly wears articles of clothing in the wrong place and says, "Oops" after the other three animals wear them correctly.
- Day 9, Story 2 of The Decameron is about an abbess who was woken up at night with a report that one of her nuns harbors a lover. She catches the girl red-handed, assembles everyone, starts lecturing her about what a terrible and unforgivable sin this is... until the nun politely points out that upon being woken up, the abbess put on her head not the required headdress, but her own night guest's pants. The abbess hurries to change the tone of her lecture to one of forgiveness and the difficulties of resisting temptation.
- Diary of a Wimpy Kid:
- In Hard Luck, Fregley has a hard time putting on a shirt and ends up with his head sticking out of an arm hole.
- Old School has Greg put his socks on over his shoes because he can't remember which order they go in.
- On the cover of the Dirty Bertie book "Pants!", Bertie is seen wearing his underwear on his head. In the story proper, he puts his dad's underwear on his head.
- In Don't Wear Your Pants on Your Head, Fred, a boy named Fred is learning to get dressed but has many issues, including wearing his underpants on his head.
- In the Little Princess book "I Want My Potty", the Princess wears her crown on her butt as part of a trick.
- Dead Gorgeous: In "150 Years Later", Rebecca—a Fish out of Temporal Water ghost—has never encountered 21st century clothing before, and assumes a bra is bonnet. She is soundly humiliated when she goes to lunch in the dining hall with the bra on her head.
- One episode of Father Ted opens with a Self-Parody joke about Ted and Dougal watching an episode of Father Ben, in which Ben's companion Brendan is wearing a pair of shorts on his head.
- The pilot episode of The Fresh Prince of Bel-Air has Will, an urban kid from Philadelphia, wearing a suit with the cummerbund around his chest at a dinner party throw by his wealthy Aunt Vivian and Uncle Phil.
- In Mork & Mindy, Amusing Alien Mork wears his watch on his ankle, and thinks it's wierd that earthlings wear watches on their wrists. It may have something to do with the fact that orkans evolved from birds, who'd want their arms free to fly with.
- During the Sesame Street song "All Dressed Up", some children arrive wearing their winter clothes in the wrong places: One girl has a galosh on her head and a scarf on her nose, another has gloves on her ears and a coat on her face, and a boy has earmuffs around his waist and a hat on his hands. Bert bluntly tells them to go away and put their clothes in the right places.
- The kids' song "Don't Put Your Trousers on Your Head" features Fred, who puts his pants on his head, and Pete, who wears his gloves on his feet (which slows him down and he loses a race).
- In the poem "Don't Think About a Zebra", it says that you shouldn't think about zebras because then you might think about zebras doing crazy things, up to and including wearing diapers on their heads.
- Amphibia: Upon introduction, Captain Grime finds one of his soldiers to be wearing a breastplate as pants.
- There's an episode of Futurama where a monkey forgets where to put his intelligence-enhancing hat, at one point putting it on his butt.
- In the Little Princess episode "But They're Mine", Princess is looking for uses for her old clothes, so she puts undies on the heads of two dolls, and socks on the heads of two plushies.
- Looney Tunes: In the Charlie Dog cartoon "A Hound for Trouble", Charlie is running an Italian restaurant while his new "master" is away, and serves a customer some freshly made wine that he just stomped the grapes for in front of him. The customer is so distraught and disgusted that when he leaves, he puts his coat on his head and puts his arms through his hat.
- The Loud House:
- In the episode "Stall Monitor", Lincoln is stalling so his parents will be late for the parent-teacher conference. First he comes out of his room with no pants, then with no shirt, then he puts his pants on his head.
- In "Driving Miss Hazy", Lincoln, who is tasked with doing Lori's laundry so Lori will take him to the comic book store, bumps into Leni, who is on her way to Lori's bedroom to make Lori's bed.note When the two pick themselves up and talk to each other, Leni is seen wearing a pair of Lori's pants on her head.
- In "Crimes of Fashion", when Lincoln is considering giving up playing superhero and discards his cape, Leni tells him he can wear it as a scarf and does so herself. Then, it's revealed that a little boy is using the missing scarves as superhero capes.
- Muppet Babies (2018): In "The Best, Best Friend", Fozzie worries that Rowlf is going to replace him as Kermit's best friend. After losing to Rowlf in a game of Tri-soccer Flying Baseball, Fozzie tries to imitate Rowlf (even going as far as wearing the latter's clothes). Gonzo then asks Fozzie why he's acting so strange, then says that he's an expert on strange, as he wears his underwear on his head. When Gonzo puts a pair of boxer shorts on his head, Rowlf says it sounds like fun. Kermit manages to talk Rowlf out of doing it by asking him to play another song on the piano.
- In a the My Little Pony: Friendship Is Magic episode "Baby Cakes", Pinkie Pie tries to change the twins' diapers, but one of them puts a diaper on her head.
- The intro for the later seasons shows a diaper falling from the sky and landing on Dil's head.
- One episode has Betty wondering if babies actually copy their parents and noting, "Last week, Philly wore his diaper as a hat. He certainly didn't learn that from me! 'Course I can't keep an eye on Howie 24/7."
- In "Dil Saver", Grandma Lulu puts new clothes on Dil, including socks on his hands.
- In "Mirrorland", Tommy believes the mirror that Didi bought from an antique store to be a portal to a dimension called Mirrorland. When he and Chuckie go to Stu and Didi's bedroom, Chuckie sees it looks the same as before, so Tommy tries to prove that Mirrorland is real by wearing his diaper on his head, since that's what a mirror baby would do.
- In "Naked Tommy", Tommy decides to take off his clothes after seeing how much fun his dog, Spike has not wearing clothes. At one point when Stu tries to put Tommy's diaper back onto his bottom, Tommy takes it off again and tosses it onto Stu's head. When Didi sees this, she tells Stu, "Get that thing off your head, you're going to give Tommy ideas!".
- In "Chuckie's Bachelor Pad", the babies believe the garden shed to be Chuckie's new home when their dads move all of Chuckie's furniture out of his bedroom to repaint it. After the babies have a party in the shed, Tommy is seen wearing his diaper on his head. When Lil sees him doing this, she giggles. Tommy then gasps, hides his diaper behind his back, and blushes.
- In "Doctor Susie", Susie decides to become a doctor for toys after Lucy teaches her how to be a doctor. When Dil breaks Angelica's Cynthia doll, Susie decides that she'll need the babies' help to fix her. When she dresses the babies as surgeons, she has them wear diapers on their heads, which act as surgical caps.
- SpongeBob SquarePants:
- In "Pickles", a supposed error on a Krabby Patty order causes SpongeBob to not remember how to do anything. At one point, we see that he put his underwear over his head.
- At the beginning of "Your Shoe's Untied", Patrick gets a new pair of shoes, and decides to wear them on his hands instead of his feet. SpongeBob likes this idea, and suggests also wearing gloves on their feet and hats on their "captain's quarters". In a later scene, Patrick is still wearing his shoes on his hands as he eats a Krabby Patty at the Krusty Krab.
- In "Grandma's Kisses", SpongeBob's grandmother gives Patrick a sweater as a present. When Patrick opens it, he thinks it's a hat and wears it on his head until SpongeBob's grandmother tells him it's a sweater.
- In the late 1930s, a trend created by Italian surrealist couturier Elsa Schiaparelli, with the help of artist Salvador Dalí was to wear shoes as hats◊.
- One old online prank by online users towards gullible women (particularly those who don't speak fluent English) was to put their shoes atop their heads.