They don't mix.
As You Know, the Magic Skirt is a trope in place to preserve the modesty of women before the audience. The trope can't be counted on to be in effect in-universe with regards to the other characters. Some skirted female characters are aware of this, and thus this trope.
Basically, a savvy, skirted woman refuses to climb, scale, ascend, mount or escalate a ladder or ladder-like device while men are nearby for fear of subverting Magic Skirt, and well, you know...
She's not always successful. But if she's lucky, not all men in-story are perverts. If it's the cameraman who does this, then it's Male Gaze. Of course, this is often a Real Life concern for women and part of the rationale behind Modesty Shorts or Skirt over Slacks, or even Proper Tights with a Skirt.
The trope's name is a reference to the popular board game Chutes and Ladders (sometimes called Snakes and Ladders).
- In a scene cut by 4Kids, during the Duelist Kingdom arc, Tea/Anzu and the cheerleading squad (lead by Tristan/Honda) were scaling a secret tower via rope. Honda suggests that Anzu go first so that if she falls they can catch her. She refuses initially, blushing and indicating her skirt. Honda doesn't understand, so Bakura explains the problem. She ultimately allows it so long as they both wear blindfolds (which eliminates the original purpose of catching her if she falls). And then the way they climb makes it a moot point, as even if the guys weren't blindfolded, they were walking up the side of the tower in a manner that prevents them from looking up her skirt anyways, except maybe when she went in the window.
- A variation happens in the first chapter of the manga, where Anzu quits a class basketball game in disgust after noticing how the boys would only pass the ball to the girls when they were in a spot where they would have to make a jump shot...
- In E's Otherwise, Yuuki, Kai and Asuka are being pursued by a killer cyborg. Escaping into the sewer, Yuuki leads them up a ladder while carrying Asuka on his back. Asuka (who's wearing a short skirt) requests that Kai go up first. Not understanding, Yuuki heads up the ladder anyway, giving Kai a perfect view (he blushes tomato-red). She cries afterwards, since Kai is basically her Love Interest (and Yuuki still never got it).
- In Bastard!! (the anime), when Dark Schneider goes off to rescue Tia from a ninja along with the royal army AND the Royal Princess, they run into a problem like this during the assault on the tower. Since the ground-floor is a battleground, DS has to go up last to protect the ladder, but the princess refuses to go up first since she's wearing a rather short skirt. (She originally wore it under a rather fancy set of armor, but DS had her take it off once it became clear that it was completely useless and very encumbering.) DS rolls his eyes, throws her over his shoulder, and climbs up the ladder with her hanging there. Thus, instead of him potentially looking up her skirt, she winds up having her boobs bouncing off his back and her hips grinding against his face all the way up. Judging from her expression, she'd probably have preferred it the other way around.
- An early episode of Digimon Frontier had Zoe suspect this trope was in effect once she was offered "Ladies First" up a ladder.
- The first time we met Kamome in Cyber Team in Akihabara, she is going first up stairs in a very short skirt providing a Panty Shot; when some boys enjoying the view remark her this, her first action is to demand money from them in exchange for the fanservice, so she doesn't denounce them as perverts.
- Komari has this worry while climbing a ladder around Riki in an episode of the Little Busters! anime.
- In Bizenghast, heroine Dinah ends up climbing a ladder ahead of her best friend and possible love interest Vincent. While wearing a very short skirt. Vincent is told, "Don't you dare look up," and complies, but turns bright red.
- Neon Genesis Evangelion. Misato and Kaji are trapped in an elevator during a power blackout at NERV. Trying to open the ceiling trapdoor, she ends up kneeling on Kaji's shoulders, warning him not to look up her skirt. Kaji clearly wants to just get out of there and has no intention of doing so, especially when Misato says she urgently has to go to the bathroom.
- Inverted for humor (and arguably the only genuine fanservice in the entire series) in the last episode of Ghost Stories Desperate to save Satsuki, Momoko has Hajime and Leo boost her into a high window in the old school building. It's only after the two boys (and the camera) look up and get an eyeful that this possibility occurs to any of them. Momoko doesn't catch on and the two boys are too embarrassed to mention it.
- Invoked in Daily Lives of High School Boys, as the boys call for Ringo to "fix their internet connection" (which happens to be a router bolted to the ceiling, requiring a stepladder to reach). While Ringo's up there, they all take the opportunity to peek, but Ringo remains oblivious. Afterward, the boys remark that doing so actually made them feel more guilty than happy.
- A variation happens the third special of Girls und Panzer, when Anglerfish Team climbs a steep flight of stairs in the school ship (unbeknownst to them, they're going up the "down" stairs). Saori desperately tries to prevent Mako from seeing what's up her skirt, but the other four girls are not nearly as concerned about this trope.
- There's a scene from The League of Extraordinary Gentlemen where Mina climbs up something before Alan, and he's clearly taking a look up her dress. Mina is none too pleased. Half the comedy comes from the fact that Mina is wearing ridiculously modest Victorian bloomers under her dress anyway... this is the 19th century's idea of Fanservice!
- The Mel Gibson/Goldie Hawn movie Bird on a Wire featured this in the trailers for the movie. Hawn's character doesn't invoke this, though, until they're halfway up a fire escape and the wind is lifting her skirt.
- Parodied in one of The Naked Gun movies. Priscilla Presley climbs up a ladder.
Leslie Nielsen: [looking up] Nice beaver!
Priscilla Presley: Thank you, I just had it stuffed. [Hands him a stuffed beaver]
- David Fincher's The Game has this. When climbing out of an elevator, Christine wants Nicolas to go first. Nicolas complains that it'll be that much harder to pull Christine up than for her to go first. Christine says that she's not wearing any underwear. A few minutes later, when they are chased by dogs in the alley, Christine doesn't hesitate. Nicolas calls her on it.
- The 51st State reverses it, with Emily Mortimer looking up Samuel L. Jackson's kilt.
- In Austin Powers: International Man of Mystery, Vanessa climbs a ladder in an extremely short skirt. Austin watches appreciatively for a few seconds before remembering he has to go beat the Bad Guys and save the world.
- Spaceballs has the droid Dot Matrix climbing a ladder between spaceships, followed closely by Barf. She tells him to "stop looking up my can!"
- Dry Summer: In one scene Osman the sleazebag tells his sister-in-law Bahar to climb a ladder and check on the dam for the express purpose of getting a look up her skirt at her bloomers. The second time he gets a look up her skirt as she's up in a tree gathering fruit; she dumps all the fruit on him.
- Anita Blake is climbing down into a sewer with a friend below her. For added fun, Anita explicitly says that if a skirt covers her buttocks, it's long enough for her, and she's wearing a thong. Oh, and she knows her friend is looking up her skirt, but is so...empowered? or something that she doesn't care.
- There's a comment at one point in the Book of the New Sun where Severian, the hero, says that he should walk in front of a female character because he's seen the state of her undergarments.
- The shop owner's wife, Judith Toumignon, in Gabriel Chevallier's novel Clochemerle is the hottest woman in the titular town. When coming to the shop, men often request an item from one of the top shelves. Guess why?
- Ladders aren't involved, but in the Xanth series, it's a good idea for a woman not to wear a skirt when crossing the invisible bridge that stretches across the Gap Chasm, as anyone walking below could look up and see what color her panties are.
- In Maskerade, Walter Plinge insists that Nanny Ogg precede him while descending a ladder, so he can't look up her dress. If any other man had mentioned it, he'd probably be due a thumping (as Nanny's in her seventies easily, and rather plump to go by official art), but he's sincere and more than a bit daft so it's clearly honest concern. As the series' Dirty Old Woman, Nanny just contemplates that this may be the first time anyone's said that to her...
- In the first Adrian Mole book Adrian helps his neighbor, Mrs. O'Leary to put up street decorations for the wedding of Prince Charles and Diana. When she climbs a ladder, he can't help noticing her knickers, which he finds surprisingly sexy for someone who goes to church every day and twice on Sundays. ("Black lace! With red-satin ribbons!")
- In Stephen King's It, it's mentioned that as a kid, Ben Hanscom always looked up when passing under the staircases in the library because once, when he was looking up for no reason, he saw the panties of a pretty high-school girl.
- In The Wheel of Time series, Elayne Trakand is lifted into a ship on a plank attached to ropes, and has difficulty with the boatman who rowed her out there staring. Aviendha (who doesn't understand wetlander customs relating to nudity) hurls a knife into a wooden post to make the boatman understand that he mustn't look...then lifts her skirts to climb over the seats and retrieve her knife before riding up. The boatman is understandably confused.
- The Takers by Jerry Ahern. Mary-Frances Mulrooney is boarding a nuclear submarine and gets a Wolf Whistle from a sailor down the hatch. An officer tells off the seaman responsible, then explains that none of the women who boarded earlier got a whistle like that.
- In 2 Broke Girls, Han accidentally looks up Caroline's skirt while she is standing on a ladder writing on the blackboard. He rushes off in embarrassment but not before thanking her.
- An Inversion: In the Doctor Who 2012 Christmas special, "The Snowmen", Clara and the Doctor ascend a long spiral staircase to a cloud where the Doctor has parked his TARDIS. The Doctor asks Clara to go first, but she refuses, telling the Doctor to keep his "eyes front". While the Doctor says he always keeps his eyes in front, Clara admits otherwise.
Doctor: ...Stop that!
- During an extended sketch on The Benny Hill Show taking place on a cruise ship Benny is standing next to a ladder/stairway when a few lovely birds in short skirts go up. He gets his eyeful, then calls a buddy over so he can peek too. As the buddy arrives and sets himself up, a Man in a Kilt starts his way up the stairs, giving Benny's buddy a glimpse of what they don't wear beneath the kilt.
- In Are You Being Served?, Miss Brahms refuses to go up a ladder with Captain Peacock standing at the bottom. He goes up himself. Then a door opens and he ends up wearing a new hat.
- The finals of Terri Runnels' "Terri Invitational Tournament", where the winning team got $100,000 and her managerial services, between the Hardys and Edge/Christian was a ladder match at WWF No Mercy 1999. To promote it, she did a promo where she was climbing a ladder while wearing a skirt, complete with commentator Jerry "The King" Lawler, in full pervert mode, looking up, though, uncharacteristically, nothing was actually shown. The fact that her top was almost open likely had something to do with it.
- In Cactus Flower, Toni, perched on a ladder stacking records on a top shelf, displays a lot of her legs to Juliannote :
Julian: Say, do you always stand up there like that?
Toni: Like what?
Julian: Well, if any customers stand where I'm standing... let's just say it's quite an angle.
Toni: [Shrugs] Oh, that. Nobody here looks. Most of our customers are classical.
- In Star Ocean: The Last Hope, the group is on top of the tower Citadel on Lemuris, they find a long cloth leading down to the ground. Edge suggests he go first to test for strength, at which Reimi complains and calls him a pervert. She gets her wish and heads down the cloth first (this entire scene makes no sense; she doesn't wear a skirt but a panel of thigh armor over top of leather shorts).
- Resident Evil 2: Ada either leads Leon up a vertical ladder (while wearing what's almost a miniskirt), or asks him for a boost up to a high ledge. Leon is clearly taking in the view in the latter. RE 4 also has at least one upskirt shot of Ada in a cutscene, e.g. when she saves Leon from Mendez.
"Leon is never one to pass up an upskirt view. No matter how contrived the reason."
- Attempting to do this to Ashley (or doing it by accident if an enemy throws you to the ground near her) in Resident Evil 4 (again, playing as Leon) will cause her to call you a pervert. Peeping from one very specific spot with a custom sniper rifle scope reveals that they are made of white knitted cotton. If you use her alternate outfits, which don't feature a skirt, she won't have that reaction.
- thedarkid's excellent Let's Play of Resident Evil 2 has a screencap of Leon getting a view up Ada's skirt. About 80% of the way down the page.
- In TimeSplitters: Future Perfect, Cortez is with the beskirted Jo-Beth for the horror-moviethemed level. Halfway through the level, they find an ominous hole in the ground with screams and roars coming from it. We then get this little gem:
Jo-Beth: (hearing the screams) ...er...you go first.
[Cortez pauses; the camera focuses on her skirt]
- Happens before the first full moon in Persona 3 where Yukari warns the MC and Junpei. However, in Persona 3 Portable she only warns Junpei no matter what gender the MC is and after Junpei retorts to her warning Yukari suggests burying him and leaving him behind. Also odd, as she wears a skirt that, in battle, would show everything if not for the fact that her legs end in shadow past the hemline.
- Though not a ladder, in Final Fantasy VII, if you choose to climb the stairs up the Shinra Tower, Tifa will eventually realize she's wearing a miniskirt directly above her two male companions, stop, and refuse to continue until you go ahead of her.
- Subtly implied in Silent Hill 3. The Otherworld transition in Brookhaven Hospital involves Heather ascending a very long ladder. About 3/4 of the way up, she passes by Valtiel, projecting 90 degrees from the wall in such a way that, if he had a face, he'd be looking right up her skirt. Given the game's near-constant imagery of molestation and stalkers, this is almost certainly intentional.
- The first game in the Disaster Report series features a point where a female character asks the male protagonist to climb up a ladder before she follows. Her stated reason for asking is: "I'm not wearing... um..." The game won't allow you to proceed until you agree. Later you can view photos stored in the camera of another character she traveled with and it reveals that he took a photo of her (clothed) butt when he climbed a ladder behind her.
- Subverted in Tales of Graces, where at one point, Cheria is standing at the top of a stepladder that would provide the character you're controlling with a clear view if you were to stand underneath her. However, anytime you approach the ladder, she'll conveniently decide to crouch down to prevent this from happening (She's shown to be wearing Modesty Shorts in some cutscenes, though).
- In The Legend of Heroes: Trails of Cold Steel, Angelica orders the boys to first go up, then the ladies, and finally her. Crow was the only one who got it and got pissed at Angelica for getting the good stuff while the rest of the girls aren't pleased when they finally climb up the ladder.
- Zig-zagged in Danganronpa.
- In the last chapter of the first game, Naegi and Kirigiri climb a ladder going up several storeys out of the trash dump, but she choses to go second to avoid this. Then in the next scene, the camera is looking straight up at both of them while they talk, and her skirt is shadowed completely. After beating the game and getting to her School Mode ending, like with everyone else's School Mode ending (male and female) Naegi wins a pair of her underwear as a prize, and their description reads (as if speaking to the male audience) that they're so black that it'd be extremely difficult to see them from any angle (meaning it's possible the player actually was looking at them the whole time). The official artbook says her skirt has "an iron wall defense."
- A lampshade gets hung on this one in Danganronpa Parody just before the two climb the "unnecessarily long ladder" (as the Lemony Narrator puts it).
- This also gets brought up later on in the series during an interaction between Komaru Naegi and Touko Fukawa in Danganronpa Another Episode: Ultra Despair Girls.
- This ends up happening in the first chapter of Danganronpa V3: Killing Harmony where Kaede Akamatsu climbs up a ladder in the library to examine the top shelves, only to realize that Shuichi Saihara is stood below her getting an eyeful.
Shuichi: Ah! S-sorry!
Kaede: Oh. So you did see them, huh... (Well, whatever. He can't unsee them.)
- This Keychain of Creation strip has Marena badgering Secret about what she saw looking up her skirt.
Ten Winds: Yet another support for the Pants Faction.
- This◊ The Chosen Four strip has Paula telling an hypothetical Jeff he "better not look up" while descending in the mole-infested mine.
- This Freefall strip does it with stairs and a tail as Florence leads Max Post up some stairs.
- Here in the Neolithic Cross Time Cafe a Scottish tiger gets quite an eyeful of a female feline as he holds the ladder!
- This The Order of the Stick strip:
Belkar: Oh, and hey, Tsukiko. On behalf of all the men in the city: Thanks for wearing a short skirt while flying. You've given me a lot to think about. Heh.
- Mace appears stunned by the view up his love interest Lilith's skirt as they descend a rock cliff together in Volume 2 of Dreamkeepers.
- In Phineas and Ferb, when one of Candace's inventions (long story) is picked up by Doofenshmirtz's hook, she's forced to dangle from the edges of her with her friend hanging on to her legs. She glances up her skirt but quickly looks down after that.
- In Futurama, uniforms for both sexes are skirted, which leads to a scene with Zapp Branigan climbing a ladder and Kif looking away, but not out of respect for his captain's modesty.
- Code Lyoko, "Is Anybody Out There?": In a Getting Crap Past the Radar moment, Odd and Aelita have to rush to the Factory in their nightwear. And when they're climbing down the ladder to the sewer, Odd's gaze is firmly set toward Aelita's pantless nightgown.
- Averted by the U.S. Navy, and maybe others. Sailors respect a lady's modesty (and perhaps the occasional Scotsman) by facing away. To hear some people tell it - not as much as you'd hope.
- The Savannah College of Art and Design had, very briefly a clear glass staircase. This was quickly replaced by a frosted glass staircase for this reason.