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Theiss Titillation Theory
The sexiness of an outfit is directly proportional to the possibility that a vital piece of it might fall off.
This basic theory underwrites Stripperiffic clothing, Impossibly Cool Clothes, and pretty much anything else you stick female characters into: what makes clothing sexy is the hope of a catastrophic Wardrobe Malfunction. The Trope Namer is William Ware Theiss, costume designer on Star Trek: The Original Series, who first codified the concept.
The theory acknowledges that this possibility is entirely imaginary: the true magic of these outfits is that no matter what She-Fu the wearer attempts, she is never ever going to expose a nipple. Not in this time slot. Having said that, the TTT takes advantage of an odd side effect: a particularily sexy outfit actually out-titillates a nude woman. Evidently, she who might become naked is more interesting than she who already is.
Particularly common in Science Fiction and related genres. However in Will and Grace, Debra Messing occasionally wore outfits that would not be anatomically feasible for a better-endowed woman.
Though Theiss was a costume designer, according to Inside Star Trek: The Real Story, by Herb Solow and Robert Justman, most of the costumes following this theory were actually somewhat more modest before being "improved" by Gene Roddenberry. According to the "Art of Star Trek" book, Theiss preferred to design costumes that only appeared to be in danger of slipping or coming off, through the use of strategically-placed sheer or skintone fabric. He was further able (forced?) to add to the effect by the censorship rules of the time regarding what parts of the body could or could not be shown (the navel being the most well-known restriction). He found he could get surprising amounts of appeal from the carefully-arranged display of areas of skin not generally considered erogenous.
Impossibly Low Neckline ("What's holding it up?"), Absolute Cleavage and Sideboob ("What's keeping those two strips from slipping off to one side or the other?"), Godiva Hair ("All she has to do is turn her head a little...") and Underboobs ("That shirt should ride up!") are common forms of thisnote The answer to these questions is "Glue and a prayer".
Compare Wardrobe Malfunction.
Contrast Fetish Retardant.
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Anime and Manga
In One Piece there is nothing holding up Boa Hancock's robe except the sheer cruelty of the universe. This is MUCH more apparent in the animated version.
And yet Rindou, her bazooka-wielding underling probably has her beat as far as this trope is concerned. Seriously, is her short jacket duct-taped to her nipples or something?
Gaap in Umineko no Naku Koro ni wears a dress that appears to have a pretty good-sized strip chopped out of it all the way down and very barely stitched back together with laces◊. It's been described as "a wardrobe malfunction waiting to happen."
Apparently the author designed Gaap like this just to mess with an employee who enjoy doing cosplays of his characters.
In Macross Frontier, Sheryl's stage outfits fit the trope enough. However, this is only an illusion as most of the time she's actually wearing a holographic body suit.
Halibel in Bleach wears a tight top exposing gratuitous underboob. Her pants, which barely consist of enough material to cover her inner thigh until just above the knee, are also held up only by a sash. Lilinette's vest also looks pretty malfunction-prone.
Though the underboob never popping out is understandable, considering part of her hollow mask covers them
This is played surprisingly in Bleach, considering how Stripperific many of the women's outfits can be. The female characters, despite fighting fairly often, suffer nowhere near as much Clothing Damage as male characters. You might be able to argue that this is because the women don't wear enough clothes to damage.
Cowboy Bebop's Faye Valentine. Particularly in the movie, which has a scene with strong rape-y overtones, wherein the one button that appears to be her top's only fixture is sliced away by the Big Bad. Given her figure, this should have resulted in her clothing flying open rather spectacularly. Since it didn't, we must conclude that her breasts are coated with an adhesive; it's the only way that scene makes any sartorial sense. Of course, since it's implied Faye dresses like that to distract people, she may need a certain amount of help keeping it on.
Yumi Komagata from Rurouni Kenshin wears a top so low that it should not be physically possible to keep up, and indeed constantly looks like it's about to fall down. Word Of God says that he's gotten letters from female fans attempting to cosplay as Yumi asking how she does it.
Princess Tutu. Princess Kraehe wears a black tutu which looks like it might fall off at any second. Episode 13 of Princess Tutu Abridged even has the cast trying to figure out how it stays up at one point.
Several female superheroes fall under this. Notable examples include Starfire whose outfit is part lingerie, part bondage gear and Power Girl◊ and her infamous boob window.
Dear God, Emma Frost.
Dagger has an...implausible◊ costume. It's gotten worse over the years, as the character has gotten better-endowed and the costume has gotten skimpier, but even in earlier days the only reasonable explanation is that the thing is glued on.
Exactly how Vampirella keeps hey costume from falling off is a mystery. (Wizard Magazine claimed that for Real Life models who dress as the character at conventions, they use aerosol spray glue.)
Return of the Jedi. Was there any more to Leia's dancing-girl costume beneath the panels of cloth hanging from front and back of the waistline? According to Carrie Fisher on the DVD commentary, there wasn't, and at times, crews standing behind her could see "all the way to Florida", as it were. Oola suffers a wardrobe malfunction as she is being dragged towards Jabba the Hutt, and again as she falls through the trap door. You can still see a short bit of the first malfunction in the current special edition. Older editions have longer scenes.
Hammer Horror movies in particular lived with this trope. Women in form-fitting see-through nightwear that could slip off their smooth shoulders at any moment.
Ursula Andress in The Blue Max. There is a protracted scene where she has a folded towel looped around her neck so that the two lengths of towel, draped strategically in front of her, both conceal most of a breast, or at least the nipples. Despite how she moves or speaks, despite how her unsupported breasts jiggle and move, her nipples are always concealed by the towel as if it was glued in place (and probably was).
Vetinari mentions this in Terry Pratchett's Jingo. "Curiously, the purpose of the nautch girl or exotic dancer has always been less to reveal and more to suggest the imminence of revelation."
All over the place in Piers Anthony works — Anthony is fond of having some characters go completely clothed, others go completely nude, and a third group go partially clothed. The first two groups are seen as more-or-less nonsexual, but the third is a major turn on.
One of the best examples of it at work is Theiss' own creation in the Star Trek episode "What Are Little Girls Made Of?" In that episode, a female android named Andrea◊ has a costume the upper portion of which is merely two crossing strips of material. Off the set, public modeled displays of this costume never failed to get a dramatically appreciative reception from at least the men.
In William Shatner's Get A Life, he tells a story about how Gene Roddenberry talked that same outfit into a fashion show at a Sci-Fi con. According to one of the people there, the model apparently had to spend the evening "beating men off with a stick". Notable is the fact that Star Trek hadn't even aired yet.
According to Herb Solow and Robert Justman's book on Star Trek, William Shatner couldn't stop hitting on Sherry Jackson, the actress playing Andrea, once he saw her in the outfit. Further, the first public modeled display of the costume was in Desilu Studios' lunch room, where Ms. Jackson entered in said outfit — according to Herb, forks stopped midway to people's mouths.
Similarly, the top part◊ of the Greco-Roman-style outfit worn by Leslie Parrish (playing Lieutenant Carolyn Palamas) in "Who Mourns For Adonais?" consisted of a single swath of cloth draped across her breasts and slung over her shoulder. Most people who were there believed that nothing held it in place except its own weight, and were absolutely certain it was going to fall off at any second. Parrish, on the other hand, knew that it was stuck to her skin via massive amounts of two-way tape which had torn off chunks of skin during the original fitting; this is why she instead wore a bathrobe during all rehearsals, even the dress rehearsal.
In "Mudd's Women," Maggie Thrett, playing the character of Ruth◊, suffered repeated wardrobe malfunctions during shooting — apparently one of her, ahem, assets refused to remain covered. (Unsurprisingly, the final version of the costume was another of Roddenberry's "improvements.") The ruined shot was saved for a Gag Reel, however.
In a male example, one scene in an episode of White Collar had Neal Caffrey wearing nothing but some very low-riding sleep pants, with a waistband that looked very loose. You could practically hear the fangirls pleading for him to bend just a little further...
Lady Gaga usually wears skin-tight clothing, bypassing this trope; but in the video for Poker Face, one of her outfits is a criss-crossing number obviously inspired by the Star TrekTrope Codifier.
Kylie Minogue's video for Can't Get You Out Of My Head features a stunning outfit that must be just about to fall off. A still image can be seen here. Apparently there was a lot of double-sided tape involved.
In the D&D 3.5 edition Player's Handbook, all of the female examples shown in the races chapter have clothing that looks almost exactly like the example pictured at the top of the page. Not to mention the Nymph in the Monster Manual, the Elemental Savant in Complete Arcane, for that matter just about any female character pictured in any D&D book.
A noteable exception being the iconic 3.5 rogue, the halfling Lidda, who's typically fully clothed from her neck to her toes. On the other hand, that clothing tends to be skintight, so...
Jessica Albert from Dragon Quest VIII. Her breasts are so large◊, and her top is so low◊, one would think her nipples were glued to the neckline, with how they never explode out—even with her idle stretching◊, her bouncing◊, or her bending over◊. The "Sex Appeal" (as her skill in the game is) of Jessica's dress is that she is essentially naked from the nipple up. As such, her top attracts much attention and many camera shots in the game.
The entirety of the female cast of Soul Calibur—with the possible exception of Hilde—are participants in this trope, thanks to the implementation of female-focused clothing damage in Soul Calibur IV. In addition to, you know, the huge quantities of cleavage and the rather unusual designs that were carried on from earlier games.
Yoshino "Haru" Harusawa of Shin Megami Tensei: Devil Survivor wears an outfit that would do Theiss proud. Looking at her sprites, it's a wonder she isn't having a wardrobe malfunction every few seconds. Needless to say she's a popular character.
Specifically, she wears what would normally be a form-fitting dress, except that it's at least two cup sizes too big for her. This makes the top half hang off dangerously low.
It doesn't help that she's constantly fiddling with the straps.
And you know how significant that is when all the character animations are expressed in a few sprites. That's right; out of say, five sprites they drew of Haru, one of them is of her fiddling with the straps.
The Angel: Her design from the original Devil Summoner, which was swapped out, but later made a glorious return for Strange Journey and the new Devil Summoner, can be described as so: a light chained blue scarf that barely covers the breasts and nothing else.
Morrigan's robes in Dragon Age: Origins. There are more Stripperiffic examples, but the loose fit, the cleavage and Side Boob indicating lack of a bra, make it look like she could escape her top during any of her magical gestures.
Final Fantasy VII: Tifa Lockhart runs around kicking ass in a white tank top, leather mini-skirt, and combat boots. Then there're her assets.
The reboot of Mortal Kombat. Most female fighters' outfits start off this way, and get only worse as battle damage sets in (to the point where the only thing that could possibly be keeping some of them on is glue or magic, and the only thing keeping them from flashing is Barbie-doll anatomy.)
In Holy Musical Batman, Robin is a rare male example of this trope. All he's got on is a shirt, cape, mask, shoes, and briefs the whole musical. It gets worse after a scene where we see Superman and Batman rip off each other's Underwear of Power.
This is parodied in an episode of The Simpsons, when it's Agnes Skinner who wears a skintight dress to Homer's award ceremony as "Man of the Hour". Homer's father, her co-host, asks, "What's holding that dress together?", to which Sideshow Mel stands and answers, "The collective will of everyone in this room!".
This is the idea behind the "fan dance" and "bubble dance" invented by the famous burlesque dancer, Sally Rand.
Gypsy Rose Lee's burlesque routines famously didn't reveal much skin; her signature move was sliding her shoulder strap off her shoulder.
Soooo many red-carpet dresses, it's not even funny. Whether it be see-through or the slow edging of a nipslip, you know that the more TTT a dress is, the more likely that's what's gonna be leading on TMZ that night.
In Brazil, this trope is invoked for strapless dresses/bikinis, being usually called "Tomara-que-caia" ("I-hope-it-falls-off").