Skirts and Ladders

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 Genre 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.

And yes, the trope's name is a reference to the popular board game Chutes and Ladders, sometimes called Snakes and Ladders. Creepy connection, isn't it?

Anime and Manga

 * In a scene cut by 4Kids, during Yu-Gi-Oh's 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.
 * 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).
 * Great Teacher Onizuka starts with this scene.
 * 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.
 * AIKa R-16: Virgin Mission uses this trope extensively.

Comic Books

 * There's a scene from 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, and Alan's expresssion is a Crowning Moment of Funny.
 * 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 Fan Service!

Film
"Leslie Nielsen: Say, nice beaver.
 * 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.

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.
 * 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!".

Literature

 * 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 Masquerade, 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 panties, which he finds surprisingly sexy for someone who goes to church every day and twice on Sundays. ("Black lace! With red-satin ribbons!")

Live Action TV

 * In Two 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.

Video Games
""Leon is never one to pass up an upskirt view. No matter how contrived the reason.""
 * 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.
 * 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.
 * Hacking the game reveals that they are, indeed, white.
 * RE 4 also has at least one upskirt shot of Ada in a cutscene, e.g. when she saves Leon from Mendez.
 * 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.

"Jo-Beth: *hearing the screams* ...er...you go first.
 * In the remake of Resident Evil 1, you can unlock Jill's RE3 outfit. There are at least two cutscenes where she falls backward or is shown from below, allowing an upskirt view. In some RE3 cutscenes, you can also see upskirt.
 * In Time Splitters: Future Perfect, Cortez is with the beskirted Jo-Beth for the horror-movie–themed 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:


 * Cortez pauses; the camera focuses on her skirt*

Cortez: Okay."


 * Happens before the first full moon in Persona 3 where Yukari warns the MC and Junpei. 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.

Web Comics

 * This Keychain of Creation strip.
 * This The Chosen Four strip.
 * This Freefall strip does it with stairs and a tail.
 * Here in the Neolithic Cross Time Cafe a Scottish tiger gets quite an eyeful of a female feline as he holds the ladder!

Western Animation

 * In Phineas and Ferb 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.

Real Life

 * Averted by the U.S. Navy, and maybe others. Sailors respect a lady's modesty (and perhaps the occasional Scotsman) by facing away.