Now the exact form of the dress doesn't matter. It can apply to grand, sweeping gowns, or mini dresses. What matters is the heavy use of fancy materials or decorations (which can be expensive, even today).
Gown Pimping Options
Many, many yards of cloth, including layers of skirts, capes, trains, and long hanging sleeves
Gloves (long, especially Opera Gloves, or short depending on the sleeve length and/or neckline). Usually white, but can be worn in colors to match or contrast with the dress.
A matching Hand Muff, Cape, Stole, Hat and/or other accessories.
Admittedly, there is no real objective line between this and a regular evening dress, so it's more a manner of how obvious it is the dress is pimped out. Say a lady has an evening dress with a fancy design embroidered onto a small part of the skirt. Fancy and stylish, but it's not that obvious, even when you see the skirt. So it wouldn't be this kind of dress. If most or all of the dress was instead almost covered in embroidered designs, it would be this trope.
Sometimes a character with a Clothes Make the Legend dress uses this trope to make her dress fancier, while still keeping its iconic look.
This trope might apply to guy's clothes (as in they aren't crossdressing), but in fiction, this type of outfit is reserved for either known historical uses, based off those uses, or else characters who are outright fops.
This will show up more often when combined with Princesses, especially Princess Classic.
A Sub Trope of Impractically Fancy Outfit.
A Super Trope to:
Marie Antoinette of course got the most dresses, with perhaps the standout dress being one that is not only trimmed with ermine, but the ermine itself is decorated with diamonds (same with the ermine on the cape). And at least in the manga, she wore a nearly identical dress for her husband's coronation.
Madam Du Barry had quite a few herself, showing her favor from the king.
Rosalie also got several.
And Lady Oscar even wore on to go on a date with Fersen.
Sailor Moon had an episode involving wedding dresses (Sailor Moon Abridged skipped over it, save for the French accent Serena inexplicably had in the dub).
There's also Usagi's Go-Go Enslavement gown when Prince Diamond captures her.
The dresses all the girls wore in episode 37 for the Princess seminar.
All of the senshi have princess dresses in the manga, but Serenity's really takes the cake with a huge train, puffy sleeves, pearls, gold, white, etc.
Jupiter once wore a long, black dress, that had a large, red rose embroidered on the skirt.
CLAMP loves this trope. If they can't work elaborate outfits into the plot of a manga, they'll add them in Omake and packaging art. Cardcaptor Sakura, Tokyo Babylon, and xxxHoLic have very noticeable uses of this trope.
Tsubasa Reservoir Chronicle. And those are just the weekly chapter splashpages. It gets even more elaborate in the other TRC art.
Mahou Sensei Negima! has Ayaka, who can often be seen wearing absurdly elaborate outfits on normal days. There's also Tsukuyomi, who wears such outfits to sword fights where they'll undoubtedly be torn to shreds. The next time she appears on-screen, she'll invariably have a new one to destroy.
Princess Fala/Allura of Go Lion/Voltron, has a fancy pink dress.
Amue, aka Romelle, has a blue dress that isn't that fancy aside from the pink frills, but her pink Mini Dress Of Power is more pimped out.
Code Geass. Almost everyone in the Britannian Royal Family, yes even the Bishōnen princes, are prone to this trope. Joining in the pimpin' fun are Kaguya◊ and anunwillingKallen.◊ No surprise considering it's by CLAMP...
Lelouch's outfit after he is crowned Emperor probably qualifies as a male version.
In the Cross Dressing Festival picure drama, Lelouch is forced to wear a very elaborate purple Victorian style dress. Nunnally really wants to see it.
The dress in Paradise Kiss. The characters actually spend several volumes making it.
Also the main character's dress in one of the previous edition of Yazagaku Fashion Contest in Paradise Kiss' prequel Gokinjo Monogatari.
Last Exile has plenty for the upper class, notably Mad-Thane's wife and daughter, and Sophia after she reveals she is the emperor's daughter.
The manga Alice Quartett, about four clothing designers who run a boutique together, has them collaborate on a Pimped Out Dress in the first chapter.
Shattered Angels has some very fancy and elaborate dresses, even for servants. School uniforms looks very elegant, especially for the boys, and the student council. Then there are the dresses worn by Absolute Angels.
The girls of the Lobelia Academy wear fancy dresses are part of the Zuka club.
Comic Books
The Snow Queen's dress in Fables has plenty of frills, a few ribbons, and a fur boa.
Jean Grey's wedding dress in X-Men has Opera Gloves, a hooded cloak, and a diamond threading pattern all over it, stopping at the flared hem.
Even her dress in her first appearance would count (given her family's moderate wealth). Even if it doesn't look fancy, the fabric was likely high end, and the clean lines and form was typical of some upper class women at the time.
Ozma's dress at the end of Return to Oz, which was based on the outfits John R. Neill drew for her in the original books.
Use symbolically in the film Diane. Diane de Poitier's dresses are opulent, but Catherine de Medeci's dresses are more so. Until one day, to show her favor with the king, Diane shows up in a dress just as grand. Even the ermine trim on the skirt is identical to one on the dress Catherine is wearing at the same time.
In the Ginger Rogers film Lady In The Dark, she wears a dress with a mink skirt. She had to wear an altered version for a dance sequence in a later scene.
The skating dresses worn by Sonja Henie in her movies
In Pirates of the Caribbean, Elizabeth gets two of these. One in the first two movies until she becomes a stowaway, then again, to some extent, when she is on Sao Feng's ship.
Queen Elizabeth in Elizabeth: The Golden Age is adorned by an astonishing sequence of unbelievable confections. Some were in what the producers cheerfully admitted were wholly historically improbable colours, just to look cool.
Labyrinth, Sarah's dress in the "masquerade ball" scene.
Esme Squalor in A Series of Unfortunate Events wears a bizarre and disturbing variant — a huge dress that looks like a fire, complete with black lace for smoke, which crackles when she walks.
Esme Squalor owns this trope in a twisted way, as she is always wearing something ridiculously pimped out because it is "In," including stiletto heels that are actual stiletto knives.
Whoever had designed the dress didn't known when to stop. They'd put lace over the silk, and trimmed it with black vermine, and strung pearls anywhere that looked bare, and puffed and starched the sleeves and then added silver filigree and then started over with the silk.
Esme Weatherwax buys one of these in Maskerade to blend in with an opera crowd.
Subverted in City Watch Commander Samuel Vimes (formerly a lowly Night Watch captain, then knighted and later made Duke of Ankh against his will) who goes out of his way to avoid wearing his hated official ducal outfits as much as possible. Given that these consist of a velvet cloak and hat, a red shirt with silly baggy sleeves, tights and puffed shorts, a "tiny shiny breastplate" and a helmet with feathers in it, while Vimes' stubbornly proletarian soul prefers a honest policeman's outfit (leather knee-breeches, leather cloak, sandals or sturdy boots, a dented breastplate and a helmet blessedly free of any silly feathers), the sartorial conflict is preprogrammed.
The wizards of Unseen University are the prime offender. They have shown a magpie-like —if magpies were a bunch of fat old nicotine-addicted men in beards— fascination with glittery accessories and tend to pimp out their robes and broadbrimmed pointy hats as much as possible. Or at least the older and more conservative wizards do. There's no use in being important if commoners cannot see how important you are, they argue. A fine example was the sentient Archchancellors' Hat, which had, among other things, a ring of blazing octarine stones affixed all around its rim which gave it "a rich and sinister tastelessness". Even more elaborate are their festive costumes, as seen during formal occasions such as the wizards' procession:
There were a lot of them [wizards] in the hall, in all their glory. And there was nothing finer than a wizard dressed up formally, until someone could find a way of inflating a Bird of Paradise, possibly by using an elastic band and some kind of gas.
Even the incompetent Rincewind the Wizzard, in his threadbare moth-eaten red robes and flip-flops, dreams of a new wizarding hat with fresh sequins and "those, you know, like glass chandelier things? Lots of those all round the rim" and its inscription Wizzard spelled with three Zs.
Every second or third set of elven clothes in any setting where elves are present and any clothes are described at all. Pretty much all clothes female dark elves wear when not Badass in a Nice Suit.
Qilue in Silverfall by Ed Greenwood came to the masquerade (for some business, not to show off) in such "[un-]dress" that everyone automatically assumed it's a "princess" costume:
Simylra: a lady... and not quite naked. She's wearing some black leather straps—here and there, you know.*
plus buttock-high boots with silver heel spikes and elbow-length gloves of the same material, plus a handful of two of silver and gems hanging from those straps
They must bear some powerful spells; her disguise is nearly perfect. Cathlona: Her disguise? Simylra: A drow princess. ...Gods, how can anyone compete with that? Cathlona: (looking for herself) Simmy, either get me a drink—a very large drink—or let me go home... Dumathchess Ilchoas "the Dauntless": ...A woman, did you say? You mean you're not really a drow princess? Qilue: A drow princess? No...
In Kushiel's Legacy, Phedre spends a while waxing lyrical about her dress before every fete, ball, masque or other special occasion. The red and black dress for her first assignation comes to mind, and the gown she wore in Kushiel's Avatar to murder the Mahrkagir with her hair-pin. When she wears a gown with a low back that shows her tattoo, she means business.
Alexander Pope, when writing The Rape of the Lock, knew better than to insert lavish descriptions of Belinda's outfits... however, considering that her petticoat alone, with its fifty-sylph guard of honor, is described in terms of which Achilles himself would have been proud, it simply follows that the dress that goes over it is equally sumptuous.
Sansa's wedding outfit. Included, partially quoting the Citadel: "a gown of ivory samite and cloth-of-silver, lined with silvery satin, with long dagged sleeves that were almost touching the ground, the bodice slashed almost to the belly, the deep vee covered over with a panel of ornate Myrish lace in dove-grey, long and full skirts and very tight waist; tight slippers of soft grey doeskin; a costly maiden's cloak, meant for a wedding ceremony, made of velvet heavy with pearls, embroidered in silver, and fastened by a silver chain." Even if not the most elaborate gown in the series, it's certainly the most Costume Porn for one.
Parodied in a short story wherein a designer makes dresses so elaborate and ridiculous that they completely obscure the woman inside. At the end of the story, the men at a garden party start to notice that the women at the party are weirdly unresponsive, because they are just talking to empty dresses. It turns out that the women are all hanging out inside the house in their underwear..
That Lady In Ermine had a few, particularly one with a lot of frills, and a crinoline skirt that had nothing underneath to show her legs.
Live Action TV
Any avant-garde challenge on Project Runway tends to feature this.
The dresses on Strictly Come Dancing, and ballroom dancing in general are often like this.
Kaylee's flouncy dress in "Shindig", along with several other dresses worn at the party (including the one it takes the space of a wink to remove).
The Academy Awards. Oh, sure, the Emmys and Tonys have pretty dresses too, but what else is the point of the Red Carpet segment? Certainly not those little interviews. The Red Carpet is made for this trope.
The "lady has no taste" version is frequently used on The Drew Carey Show with Mimi. Her wedding gown was covered with giant flower buds that opened at the culmination of the ceremony.
Ace foregoes her usual bomber jacket for one of these in the Doctor Who serial Ghost Light. Once she's done crossdressing, that is.
The first three Blackadder series had quite a few, particularly Elizabeth's dresses in the second series.
Dynasty, especially when it came to shoulder pages, or anything that made the dresses sparkle.
Elizabeth R of course has several, worn by Elizabeth, or others. The first episode (when she's still a princess) notes that her dress with ermine sleeves is her finest gown.
The cover art of almost every one of Enya's albums depicts her wearing this sort of dress; notable examples are The Memory of Trees, Amarantine, And Winter Came, and The Celts. She also wears similarly gorgeous, sumptuous dresses in her music videos, such as "Caribbean Blue", "The Celts", "Only If", and "On My Way Home" (the latter also being an example of Pretty in Mink). Even her more simple dresses are still stunning and elegant, but with her ethereal beauty she could make almost anything look beautiful. (Almost anything. The power business suit for "Anywhere Is"...doesn't really do her justice.)
Barbie has easily one of the biggest collection of pimped out dresses of any fictional character ever. The line even has collection sets just for making nothing but more pimped out dresses. These include:
The HappyHolidays line, along with many other Holiday lines.
While Rozalin's dress may not be the most extravagant dress in the history of fiction, it certainly comes close: petticoats, flounces, Detached Sleeves, ribbons, pearls, jewels, bows, jewel encrusted bows, gold-laced shoes, wings (which, while not technically part of the costume, are held in a way to resemble the biggest shoulderpads known to man), and a matching designer gun.
The Fairlions in the Super Robot Wars Original Generation series. Yes, they're Humongous Mecha. But they were made as showpieces for the princess of The Kingdom, and piloted by she and her BadassGothic Lolita bodyguard. The Angeleg is also similar to this, with added wings, of course.
Princess Peach's dress started out pretty simple, but as graphics advanced, it got more pimped out. First was a small overskirt and a brooch over her chest. Now in Super Smash Bros. Brawl, her dress has several layers of overskirts, lace trim, pleats, and gold decorations.
Zelda didn't have a defined or even fancy dress in game until Ocarina of Time. Since then, they've always had some of the elements of that dress: a pink-to-purple top half with a gold emblem over the chest, a white-to-rose skirt with a banner showing Hyrule heraldry hanging from a golden belt, and her golden diadem with a massive jewel (always red, except for in Twilight Princess) at the center. She almost always wears Opera Gloves, gold shoulder guards attached to her chest emblem, and occasionally a cape. The younger Zeldas don't wear the big Triforce-shaped earrings that the older Zeldas do. TwilightPrincess Zelda wears two sets of smaller earrings and has the most Gem Encrusted, pimped out dress of all.
The GBA remake of A Link to the Past also gives her a fancy dress; however, said dress is actually an exact copy of what she wears on the Japanese box art on the original NES release.
And also from TwilightPrincess, there is Princess Agatha's dress.
From Wind Waker, the same dress is worn by Mila until her family loses its fortune, and then by Maggie when her family becomes rich.
A deceptively toned-down example occurs in Final Fantasy X: Yuna's wedding dress had a five-foot-long train that was trimmed and lined with feathers, a pair of feathery wings on the back, and her veil was long enough to reach the ground and extend past her train. She also had a tiara, gloves, and in addition to her actual bouquet, there was another one in the middle of her wings.
Lulu's dress, on the other hand, is immediately increased a level by the gigantic black lace, the low-cut fur collar, and three gazillion belts. Ironically, it's easier to pull off than Yuna's wedding dress (what with fur, lace, and even the gajillion belts being easier to find/make than hundreds of pure-white feathers), but a common cosplayer complaint is that they need at least two people to help them walk from the weight of the belt-skirt.
Rosa of Final Fantasy IV got a rather extensive upgrade for the DS version - they added even more jewels, a tiara, and a second cape apparently made of lace, as well as lace tights and sleeves.
Touhou features many "monsters" that, to fit its theme, turn into Moe Anthropomorphism forms of the monsters they are supposed to be. In cases like Yamame, who is supposed to be a spider monster, her only (outwardly) monsterous features are in the clothing she wears.
Everyone in Magna Carta: Tears of Blood has pimped out dresses taken to the extreme.
In Tales of Monkey Island, Elaine Marley-Threepwood gets one when she willingly becomes LeChuck's demon bride in Chapter 5, and she wears it through the remainder of the chapter, even when she reverts to her normal, no longer demonic form. And get this: her black bridal dress comes with a revealingGem Encrustedblack bustier/corset worn under a see-though sheer black fabric sleeveless blouse (which is probably veiling her Sideboob) with a black sash belt around her waist, a dark gray broomstick skirt and black dress boots at the bottom, along with gem encrusted black Opera Gloves, and an eerie-glowing blacktiara. This is made even more sexier when she reverts to normal (and the black crown no longer makes an eerie glow) both during and after Guybrush's battle with LeChuck!
Pimped out dresses (any clothes for that matter) is a staple of GranadoEspada.
Visual Novels
Fate/Stay Night's Saber gets extra points for not only having a Pimped Out Dress, but one that's further pimped out with plate mail. It's to be expected, though: most of the examples here are merely princesses, while Saber is a king. King Arthur, to be precise.
Umineko no Naku Koro ni's witches all seem to get this, as well as one or two members of the Ushiromiya family. Beatrice's dress is by far the most elaborate, considering she's one of the main characters.
Don't forget Shannon◊, she has one skirt on top of a miniskirt, a corset, and several buckles. And she's just a servant.
Cherry's ceremonial dress in RPG World. Which as Hero noted, really raised her polygon count (since the comic is about a 3D video game).
Drowtales has some pretty elaborate costumes, but the dress worn by the Empress Diva'ratrika (though only seen for one panel and in concept art) is especially fancy. Note that the moon decoration appears to be part of the dress itself. She appears much more in the side story "The Longest Wait", which is actually centered on her, though that version of her outfit is much less fancy.
Erika's new dress in strip 1222 is definitely pimped out. It's kind of hard to describe coherently but it certainly gets an impressed reaction from Largo (whose own clothes are rather blinged out as well, complete with hamster and a Nice Hat that looks like he stole it from Girl Genius).
The bread and butter of the "Harvest Festival" arc from Las Lindas. Thanks to Digit, all the girls get suitably pimped out dressed, and even Alejandra got in on the act...though hers didn't stay on for long
Darths & Droids had a number of jokes about Amidala's dresses, from guessing their armor class, to some funny foreshadowing when Jim is told not to wear the dresses when he's a Jedi, but ends up playing Amidala later on.
There are quite a few games on the web which involve using sprites to make Virtual Paper Dolls, which allow mixing and matching to make pimped out dresses.
Ebrellin in Peacock King Trilogy is described as a character that looks like a 'parade float' when he isn't naked.
Western Animation
The Disney Princesses have a fair amount. Their many fancy dresses could fill out this trope by themselves, but in their merchandising, the dresses are fancied up even further. A few sets trim the dresses with fur. Another set turns all the dresses gold. Another trims all the dresses with jewels (and that actually comes in two varieties: a set with them just wearing the dresses, and a set with them wearing the dresses and Ermine Capes).
Cinderella is an unusual example of actually showing the pimping-out process, featuring a scene in which her animal friends pimp out her ball gown. Although her iconic dress was instead made with magic sparkles.
In Sleeping Beauty, the fairies make one with their magic, but they end up fighting over the color, and the ensuing flashy light war gave away where they were hiding.
Despite being elegant enough to deserve its entry here, Aurora's gown is one of the closest examples to Modest Royalty in the Disney Animated Canon.
Disney made quite a few paper doll books based on their princesses with outfits they didn't wear in the movie. Even Pocahontas, with her modest wardrobe got a paper doll book with outfits of the Braids, Beads and Buckskins variety. Made before the direct-to-video sequal, but had a page that said "Later in life, Pocahontas went to London. These are some dresses she would've worn." It showed a couple of dresses in the fashion of that era.
The Princess and the Frog has a number of old-fashioned ones, though they are all either explicitly costumes or magically conjured. Tiana does wear a fancy conventional wedding dress and evening gown at the end.
Princess Kida of Atlantis from Atlantis: The Lost Empire is a notable exception to this trend, as well as to the official Disney Princess line-up, for the sole reason that the movie she was in sunk at the box office.
Princess Jasmine from Aladdin has a few outfits that fits this trope, all of them cheerfully combining it with Bare Your Midriff.
In a Shout Out to Beauty and the Beast, one episode of Gargoyles had Elisa Maza wear Belle's golden ballgown on Halloween while Goliath wore Beast's dress suit.
Ariel gets a few in The Little Mermaid: The pink luncheon dress, her wedding dress, and her dresses in the sequel.
In the tradition of Disney, Don Bluth's movie Anastasia includes not one, but three pimped out dresses - a gorgeous, pale yellow dress with a blue sash and strings of pearls, (and an Imperial Russian tiara, bien sur), which Anya dreams up during "Once Upon a December;" the very simple, dark blue strapless dress that she wears at the Parisien Opera (the train, however, certainly gives this dress its due of sparkles); and the dress that she wears during the celebration her Grandmama holds.
Yzma sports villainous versions of this trope in The Emperor's New Groove. At one point, the huge ribbed wing/collar... thing.. attached to her current outfit falls off, and she hastily pushes it out of sight.
In Kim Possible: So the Drama, Kim is seen wearing a mildly pimped-out prom dress, which gets charred by a Diablo's laser beams, prompting her to shout, "Do you know how much babysitting I had to do to buy this dress?"
Daria has a few, some in the show, but most in the credits pictures.
Quinn's middle ages dress in "Fair Enough".
Erin's wedding dress in "I Don't".
A number of dresses show up in American Dad, for various reasons.
Rarity from My Little Pony Friendship Is Magic is a fashion designer with a penchant for creating these. Yes, even though she (and most of the rest of the cast) are talking horses who don't normally wear clothes.
Indie clothing designer Skin.Graft has copious amounts of fancy (and Goth) as one of its hooks. Just check out their wedding gowns.
Just about any coronation dress by default, men and women.
In Britain, even the peers and peeresses are required to wear ermine trimmed robes and dresses for the coronation. One of the more notable of these is worn◊ by Consuelo Vanderbilt◊. Notable due to her being part of that famous Gilded Age family.
Also, courts such as Versailles, and the British court until recently, practically required such dresses.
Speaking of the Gilded Age, this trope probably accounted for a third of the reason it's called that.
Marie Antoinette usually followed this trope, since her position required she wear the best dresses, but she once caused an uproar for wearing a dress in a painting that was actually simple◊. It's essentially like seeing the Queen Elizabeth II wearing only her underwear for a royal photo.
The website Go Fug Yourself shows when this phenomenon goes too far.
One of her most famous dresses, depicted in the Rainbow Portrait◊, is crammed not only with gorgeous details but gorgeous symbolism. Highlights include both Ancient Greek and Biblical references, as well as a motif of eyes and ears conveying how no part of the kingdom was hidden from her.
The Pope's vestments are often this.
Dresses in competitive ballroom dance are almost always this.
It used to be the fashion for boys up to around five to wear dresses like their sisters, and some could still be quite elaborate. Take this portrait◊ of a prince of France in the mid 18th century. It's like a miniature version of a dress worn by his mother◊ and then his sister.
Fashion designers love to make these, whether they are the impractical dresses on runways, or the slightly more practical dresses on red carpet events.
Diane Kruger has worn a number of dresses by Karl Lagerfeld.
Tsarist Russia actually had a Dress Code to help make their dresses distinct from the rest of Europe's aristocracy.
Eve Torres, at awards ceremonies, and once won a match in an evening dress.
