In The Roaring Twenties, when fashion was in a big upheaval compared to the decades before, Coco Chanel came up with a dress that would work in any evening or formal occasion, and blend in through any decade since. In short, she made the Ninja of dresses. (Some say that it went all the way back, though, to Lilly Langtry, who when she first came to London had only one evening gown, which was black; she told everyone she was in mourning for her brother.)
The Little Black Dress is pretty much what the name implies: a dress that is black and is little (although it can have a full length skirt). It usually comes without decorations, but can still have some trimmings as long as they are sparse and don't risk dating the dress.
The exact style can vary, working with many types of necklines and skirts, although since The Sixties, shorter skirts are more common.
This versatility and ability to work with any shot made the dress immensely popular with Hollywood costume designers, which spread the dress's popularity around the world.
Despite how it seems, this isn't really the opposite of a Pimped Out Dress (and may rarely even overlap with Happy Holidays Dress). It's just the pimping out is rare, to a lesser degree, and still done in a way that makes the dress last.
But not every style of this dress is guaranteed to last. Many such dresses from The Eighties are more likely to be an Outdated Outfit.
Compare Lady in Red, Woman in White, Princesses Prefer Pink, Fairytale Wedding Dress.
Contrast Fashion Dissonance, I Was Quite A Fashion Victim.
Not to be confused with Woman in Black (although they can overlap), Launcher of a Thousand Ships (the shipping trope formerly named this).
Kuugen Tenko in Wagaya no Oinari-sama dons one of these in episode 22. Bonus points in that she fights a wolf woman while wearing it and doesn't even get it dirty!
One-time villainess Eris from Slayers had a Stripperific variation of this trope.
Jean Grey has worn a few. One in X-Factor #1 in a scene where she meets Scott again, and then declares she won't stand by with mutant hatred growing.
Another was worn in #51-53. The dress is obviously not meant to keep warm in winter weather, so she buys a fur coat, a white one, to complement the dress.
Tsuruya in Kyon: Big Damn Hero has one, and she wears it to a movie. With Kyon, his sister and Miyoko.
Film
Breakfast at Tiffany's has probably the most iconic example with Holly Golightly's dress, designed, like all of Audrey Hepburn's costumes for the film, by Hubert de Givenchy.
In Mrs. Doubtfire, Miranda has a couple dresses to wear for her date. Daniel in disguise tries to convince her to go with the older, and more frumpy, black dress, and it doesn't work.
Double Subversion in True Lies. When told to "dress sexy", Helen puts on one...with huge frills that seriously date it. Then she looks really hard in a mirror and rips the frills off as part of her impromptu self-makeover. Now we're talkin'.
Angela in Angel-A wore one, looked ridiculously good in it
Audrey Hepburn's little black dress in Sabrina. It was actually designed by Hubert de Givenchy, but in a power grab, Paramount costume designer Edith Head took credit for all of the clothes worn in the film.
Literature
There's an actual publishing company, specialising in Chick Lit, called Little Black Dress Books. Including this trope in some form is probably a contractual obligation.
Used as a metaphor in Al Franken's The Truth (with jokes). Al quotes a blogger who referred to the 9/11 attacks as "Bush'sLittle Black Dress" — just as the dress can be slipped on for any social occasion, the 9/11 attacks could be used as the justification for any policy he wanted to pursue.
Nicci of the Sword of Truth wears one of these all the time. It's symbolic of her unfeelingness and becomes associated with her being "Death's Mistress". In fact, when she's worried she might be recognized when she doesn't want to be, she wears a red dress and relies on her ... assets to distract.
One episode of CSI: New York had a trio of female crooks who robbed a jewellery store while dressed as Audrey Hepburn in Breakfast at Tiffany's.
In the premiere of Buffy the Vampire Slayer, Buffy is shown holding up dresses in front of her to decide what to wear to the Bronze. Her comment on the black dress is "Hi, I'm an enormous slut!" Sure enough Buffy wears a little black dress while doing her notorious Mating Dance with Xander the following year.
Music
She was a long cool woman in a black dress...
"Oh, baby, you're a classic, like a little black dress..." - Fall Out Boy, Tiffany Blews
"Gettin' You Home" by Chris Young makes use of this trope.
In the music video of Selena Gomez's "Round and Round", she wears a black dress under her trenchcoat.
In the chalga song, "Moqt nomer" by Teodora & DJ Jerry "Little black dress next the skin
Leaf from Pokemon Red And Blue. She never got to wear it outside of an official art though due to her not appearing until FRLG due to space shortages.
One of Dizzy's pre-fight animation in Guilty Gear X.
A female Commander Shepard can wear two over the course of the Mass Effect series:
In MassEffect2, Commander Shepard gets a leather one that squeaks in Kasumi Goto's Loyalty Mission. Once finished, the dress becomes available as casual wear aboard the Normandy.
Mass Effect 3 offers a spaghetti strap little black dress as part of her casual wardrobe. This one even includes her N7 logo.
Rayne in BloodRayne 2 begins the game in a black evening gown. Floor length with long slits up the sides and Absolute Cleavage; the little fabric remaining is thin enough to cling skin-tight.
Carmelita Fox from Sly Cooper has one that she wears when not suffering from Limited Wardrobe syndrome, most noticably in the second game when attending a lavish party, and during the ending cutscene of the third game.
Either inverted or subverted in Rosenkreuzstilette, where Luste Teuber actually wears little black underwear, fingerless elbow gloves, and Zettai Ryouiki.
Lara Croft wears a very Fanservicey one of these during the Japan mission of Tomb Raider Legend.
Webcomics
In The Chapel Chronicles, the main character, Chapel Smith, wears a little black dress in almost every strip. It’s one of her fundamental characteristics.
In El Goonish Shive, during the Grace's Birthday arc, Nanase gives Ellen a little black dress to wear. It's the first time Ellen, an Opposite-Sex Clone of Elliot, has ever worn anything remotely feminine, and she's quite embarrassed by the ordeal.
Kim Possible wore one of these in "Emotion Sickness", to show that she's feeling a bit saucy towards Ron. It has since become a cornerstone in the show's fandom, eventually earning the Fan Nickname "The LBD".
Frankie from Foster's Home for Imaginary Friends wore the LBD in three episodes for separate occasions: a dinner date ("Frankie My Dear"), a red-carpet movie premiere alongside Mac ("Ticket to Rod", although neither of them actually end up going) and a fund-raising party ("Fools and Regulations").
Also worn by Drew Saturday in The Secret Saturdays episode "Guess Who's Going To Be Dinner" when she and Doc go on an anniversary date.
As of the website's first update in over a year and a half, Ruby Gloom's heavily-expanded wardrobe (which originally consisted of a medium-sized black dress, which actually seems to have been pushed out of the picture entirely) includes such a dress.
Several in Batman: The Animated Series, given that Bruce hangs out around affluent people. Even Barbara Gordon has a mini one.
In one episode of Justice League, in order to get acquainted with society, Wonder Woman decides to attend a formal ball, wearing a new, nice, black dress.