Some characters wear a realistic outfit, to the point that a cosplay of them might be relatively simple. But this gets kind of boring; it's not a challenge for the cosplayer to put together, and very few people will actually realize that he or she is in costume. (Which might explain why even mundane series tend to gravitate towards unique school uniforms and such).
Sometimes the character designers realize that their characters' wardrobes are too realistic. One way to compensate for this is by mixing bits and pieces of what might be a number of perfectly acceptable outfits into a bizarre Frankensteinian mess. The outfit may be comfortable, but something about it just looks slightly, but not totally, off.
Often involves Too Many Belts, Goggles Do Nothing, Virtual Paper Doll (with some questionable mixing and matching), Impossibly Tacky Clothes.
See also Rainbow Pimp Gear, where video game characters achieve this effect due to their ideal gear being unfortunately mismatched, Seriously Scruffy (when the character's odd outfit is down to stress) and Improvised Clothes.
Contrast Pimped-Out Dress, which could have loads of accessories, but (usually) in a stylish manner.
Most of the Digimon cast's outfits — in particular, the liberal use of goggles and gloves. The reason the franchise's homepage is linked and not individual series is because it would be faster to list aversions than go through each series's weirdly dressed characters in list form. In fact, the only total aversions are Hikari in Digimon Adventure, Iori in Digimon Adventure 02, and four minor characters in Digimon Frontier. Digimon Savers actually got backlash for generally neutralising the weird clothing, with the result that Digimon Xros Wars sees the return of the rummage sale rejects in truly spectacular force. Comparatively Digimon Tamers also toned it down somewhat; only Hirokazu's clothing - and at a stretch, Ruki and Jenrya's - couldn't pass for normal.
Digimon Adventure 02 provides some justification in that the strange clothing, excluding Takeru and Hikari, is automatically applied to the Chosen Children upon arriving in the Digital World; their outfits in the real world, again excluding Takeru and Hikari, are much more normal. Said Digital World clothing is said to be a manifestation of how they see themselves and, well, they're all eleven or less. Some individual cases and situations are also justified, such as Ryo.
Naruto's safety-orange hued jacket and pants certainly stands out. On the few occasions where Naruto isn't wearing his jacket you can see he has some sort of layer of chainmail under it, which explains having something so loose if not the color. By the time of the second series he abandons the goofy looking orange jumpsuit in favor of a slightly less goofy looking orange jumpsuit.
Lee and Guy's green jumpsuits are acknowledged as goofy looking by almost everyone but them and Naruto.
In Magical Girl Lyrical Nanoha, the outfit one's Transformation Sequence results in is called a "Barrier Jacket", and is partially determined via the subconscious. As the series progresses, more and more barrier jackets are a pastiche of random pieces of medieval armor, capes, military uniforms, and exaggerated modern teenager apparel. Which actually makes sense, as later characters have more exposure to different cultures (Belka, Midchilda, and Earth) with those aspects.
Haruko from FLCL is a big example. Naota isn't; cosplayers are only recognizable as such due to Limited Wardrobe.
Handwaved in Saber Marionette J, where Lime originally shows up in a fairly standard android jumpsuit and, because of Otaru's poorness, really does get her newer outfit from a rummage sale.
Solty Rei plays with this when, during a shopping trip, the main character goes through a series of fairly reasonable outfits. Without looking, her guardian assures her to just pick the current one, and she does out of affection — a tightcute, orange jumpsuit with clunky boots number the other women look embarrassed about.
The Bount in Bleach had strange accessories like headphones and chains to make them look less normal.
The school uniforms in Princess Tutu are distinctive enough (and odd enough) that they don't fit under this...but what the characters like to wear outside of their uniforms are just normal enough to make you scratch your head. Ahiru wears big poofy yellow shorts and a midriff-baring sweater that is appropriately bird-like, while Fakir seems to be wearing one of the standard boy's dance outfits...except that he has inexplicably torn up the top and haphazardly sewn it back together.
Chrono from Chrono Crusade has an outfit that at first glance seems distinctly anime, but when he takes off his coat it's apparent that he's wearing what would be a normal outfit for a young boy living in New York during the 1920's — as long as you ignore the bright red color of his shorts, anyway.
Kino, of Kino's Journey is a fairly subtle version of this. She looks to be wearing normal traveling clothing most of the time, but then you realize she's wearing two trench coats of completely different designs, a hunting cap, goggles, a dress shirt, pants, a belt with a ridiculous number of pouches, a second belt for her gun, a boatload of weapons, a scarf, and metal wrist guards. As a traveler, clothing is supposed to be practical rather than pretty, but it seems overkill until the later episodes.
Very often, Mikako from Gokinjo Monogatari ends up with a case of this in her attemps to dress in a way that is absurdly flashy, original and/or outlandish.
Sadamitsu in the Tokyo Arc of Otogi Zoshi looks particularly ridiculous. His jacket - an orange and yellow thing with Cupid-style cherubs on the chest and a large red heart in back - is bad enough, but he supplements this with a midriff-baring black shirt, shiny leather pants, studded leather wristbands, a silver medallion necklace, and some skull jewelry on his hands.
Raikou Shimizu of Nabari No Ou is a triumphant example, sporting a sleeveless... jean-jacket... thing in combination with black hakama and colorful bracelets (plus pink hair and a huge number of talismans...) And it gets worse◊ when he's stressed out.
One early episode of Yu-Gi-Oh! GX featured a masquerade party where the students dressed like Duel Monsters; Judai got a little confuse, and combined the costumes of several monsters (Saggi the Dark Clown, Breaker the Magical Warrior, Celtic Guardian, and Gearfried the Iron Knight). Fortunately, even he eventually realized he looked ridiculous in the mishmash costume and ditched it.
Jack Ryder actually got his costume from a costume shop's rejected costume parts. And it shows. In Batman: The Animated Series he acquired the costume from various clothes in a Vintage Clothing boutique.
Alan Scott got his costume from a theatre's box of spare costume parts.
Ditto for Jack Knight as Starman, whose costume is something he pieced together in a few minutes from things he hadn't sold in his secondhand shop.
Jubilee before she got depowered. Her costumes were probably inspired by the anime look, but she's the comic book example that jumps out as having WAY too many accessories. Her most infamous attire is a bright yellow trench-coat, huge hot pink wrap around glasses, and what looks like giant dishwashing gloves, and this was worn over shorts and a red shirt. Given that she debuted in The Eighties... Word of God is that the outfit was deliberately designed to look like a Robin costume made out of actual clothing.
Wonderfully Lampshaded in the Marvel vs DC Crossover: Robin appears out of nowhere in front of Jubilee and she just replies (paraphrasing) "Nice outfit." They end up as potential love interests before battling.
Subverted with Manhunter, whose costume was assembled from whatever super-weapons she could grab from the evidence room. It looks Bad Ass.
One incident forced Tony Stark to don pieces of costumes from his fellow West Coast Avengers to retrieve one of his missing armors. Hawkeye ended up giving him the joking name "Spare Parts Man". Thankfully, he retired that "armor" pretty quickly.
Tyler Durden's wardrobe in the movie version of Fight Club is a combination of retro Impossibly Cool Clothes and deliberately shabby rummage sale clothes that perfectly convey Durden's iconoclastic-rebel-hipster personality. The fact that they look so cool is aided enormously by the fact that they're worn by Brad Pitt. Word of God is that the tacky pink bathrobe he wears in one scene actually belonged to his girlfriend at the time.
The Dark Knight: The Joker was apparently designed with this look in mind, to seem as though his outfit was pieced together from different suits he'd stolen. Surprisingly, the cops who tried to determine his identity from his possessions discovered that the entire suit was custom-made.
Diane Keaton made this look famous in Annie Hall, even inspiring a fashion trend (people are likely to know what the "Annie Hall" look is without knowing a thing about the movie).
The Puma Man costume definitely qualifies. Khaki pants and a poncho do not a superhero costume make.
Then there's the absurdity sported by the title character of Wild World of Batwoman, whose costume resembles neither a bat, nor a woman. The actress actually made her own costume, although what she was taking at the time is a mystery to the ages.
Most pirates in the Pirates of the Caribbean series. Justified as most of their gear is either plundered, or scrounged, or bought from some remote colonial port.
In David Eddings' Belgariad series of novels, Belgarath developed his trademark vagrant's outfit on purpose in order to pass mostly unnoticed. While everyone thinks that his ragged tunic and mismatched shoes are remnants of rubbish heaps, the entire outfit was custom tailored, including a tunic that has patches over intact cloth, and his mismatched boots were custom-made by a master cobbler and fit perfectly—after Belgarath spent a full day patiently explaining to the craftsman *why* he didn't want them to match and wanted them to be scuffed up a little after they were made.
Most of the time, when characters in the X-Wing Series have their clothing mentioned at all, they're in pilot's jumpsuits. But in Wraith Squadron, when three Wraiths doing The Infiltration are passing as wild-shirted tourists, well - better just to quote.
Wedge shook his [pile of clothes] out. A short-sleeved tunic in orange and yellow tropical fruit patterns and short pants in lavendar. "I'm going to throw up." [...] Donos looked mournfully at his outfit: a shirt with thin red and green horizontal stripes and shorts with black and white vertical stripes. "Sir, permission to kill Face?" [...] Face unfolded his own fashion disaster. A black silken shirt with a variety of insects picked out on it in glittery silver, shorts in a brighter, more painful shade of orange than that of New Republic pilot's suits, and a red kerchief for his neck. "As you can see, I saved the best for myself."
Later in the same series 'Red Flight' are told to dress in the local Feudal Future fashion for a diplomatic dinner. Wedge, Tycho and Wes choose nicely coordinated outfits, but Hobbie throws together random colours and styles from the wardrobe on the basis that:
"There are three types of dress clothing. The kind that offends the wearer, the kind that offends the viewers, and the kind the offends everybody. I'm going for the third type. Fair is fair."
Claudia from The Babysitters Club series was described as wearing the wackiest outfits possible, often a mismash of clothes from clashing social situations (ie, a tutu, combat boots, baseball jersey, and top hat) usually followed by the sentence, "On anyone else, it would have looked crazy, but on Claudia, it was fabulous!".
One book includes a minor character who constantly wears incredibly tacky pants and brags about how little he spent on them.
In American Psycho most of the other characters apart from Bateman embody this trope. The clothing they are all wearing is fine if you don't think about it too much. However the second you start to imagine what all the other characters are wearing your quickly realise that they would all look really stupid.
In Lonely Werewolf Girl Agrivex deliberately dresses in the worst faux-punk outfits she can create as a way of rebelling against her fashion obsessed, always immaculately dressed, Aunt.
Many of the more ignorant wizards and witches in Harry Potter tend to err towards this when trying to pass off as Muggles. This is partly due to the majority of wizarding society secluding themselves from the Muggle world (thus not really interacting with them much, if at all), and/or dressing primarily in long robes and other such similar items.
Those who do fare better tend to be either Muggle-born or half-blood (thus, usually in the constant presence of Muggles), or they study Muggles (as Mr. Weasley does, thus ensuring his children pick up this skill from him).
Willy Wonka wears a suit that would be positively natty, albeit more appropriate for a Stage Magician than a chocolate factory owner, if not for the strange colors involved: plum-colored tailcoat, bottle-green trousers, pearly-gray gloves, black top hat. Tellingly, the two movie adaptations tone this down into coordinating but still-whimsical ensembles (and have him clean-shaven — he's written as having a black goatee — to boot)...but the 2013 stage musical chooses to take the original description and push it further (teal lapels and cuffs on the coat, an orange vest, contrasting patterns on the vest and pants...), resulting in quite an eyeful. Of course, this is a reflection of Mr. Wonka's extreme eccentricity.
Various incarnations of the Doctor take this approach to their outfits. The later versions tend towards less outlandish but nonetheless distinctive looks.
The Second Doctor had a many-pocketed, unkempt coat to go with his 'space hobo' look.
The Third Doctor wore velvet smoking jackets and frilly shirts that the actor himself (Jon Pertwee) had worn precisely because they looked silly. He also wore a cape most of the time. And his hair, fluffed out with rollers because the actress playing his companion teased him about his bald spot, slowly increased in size as his tenure went on. He also had a tattoo (in the 1970s, before it was cool).
The Fourth Doctor actually has a well-coordinated, if anachronistic, outfit - a poet shirt and pirate boots - but buries it under an oversized coat, huge hair and a hideous and ill-matching scarf significantly longer than he is tall, with awesomely disasterous visual results. Tom Baker binged on charity shops while picking his outfit, but the scarf was a happy accident (they bought too much wool for the old lady who knitted it expecting her to only use what she needed to make a normal scarf, but instead she thought she was supposed to use it all up).
The Fifth Doctor's red-trimmed cricket outfit and decorative vegetable. Not many men can pull off a decorative vegetable.
The Sixth Doctor's ridiculous clown suit (to match his ego-inflated personality). At a who-con in Tampa, Colin Baker (The Sixth Doctor) told the audience that he had chosen his garish coat specifically because he didn't have to look at it.
The Seventh Doctor's question-mark sweater (with question mark-handled umbrella) which might just have gone too far.
Subverted by the Eighth Doctor, who stole his outfit from the locker of someone who was going to a costume party. After rummaging through and apparently giving a certain amount of consideration to some really costume-y things, he settled on a rather peculiar but elegant Edwardian suit.
The Ninth Doctor averts this: his dark pants, dark-colored v-neck t-shirt, and a black leather coat coordinate nicely — though the coat may not be the best thing to be wearing in WWII England, as Captain Jack notes.
The Tenth Doctor wears a brown pinstripe or blue suit (it varies) with an open collar shirt, a tie and... Converse trainers (in three varying colors). Not to mention the duster. Believe it or not, the whole thing works.
The trainers-with-suit looked odder when Ten's stint started than it does now, since while it hasn't exactly become a trend, it definitely has its imitators.
The Eleventh Doctor got most of his outfit from what was lying around in a hospital while he was fighting two Starfish Aliens. The old professor outfit with a bowtie is actually one of the more "normal" ones.
And at the start of the next season, he has a stetson. However, River Song doesn't like him in hats and has an... unambiguous way of demonstrating this. The last twoepisodes of Series Six and the trailer for Series Seven, plus Word of God courtesy of Matt Smith, show that the Stetson is here to stay.
For a modest man, James May on Top Gear has a collection of incredibly loud shirts. He especially favors a purple-and-pink striped number. One of them, a white shirt with a blue flower pattern, even has its own fanbase. Lampshaded by the man himself during an episode of James May's Man Lab, when he presents a rack full of said shirts, and then proceeds to pull out the infamous purple-and-pink one...
The use of this trope also turned into a Running Gag in series 12.
"Are you wearing that for a bet?"
Mason from Dead Like Me likes to take the layered look a bit too far and is very rarely seen wearing fewer than three tops at once, often paired with some shabby-looking Fingerless Gloves, stolen accessories, and maybe some hideous ankle-zip trousers.
Harper goes beyond this and into crazy costumer, since she makes her own outfits.
Gunter and Tinka from Shake It Up are never seen without these kind of clothes. At one point they wore burglar outfits and they sparkled.
Janet Donner, a one-off character from the Eerie Indiana episode "The Lost Hour". She spends most of the episode in an outfit that would almost look normal were it not for rampant over-accessorizing: Every inch of the front of her coat is covered with pins and brooches, her belt similarly has various items hanging off it, and her earrings are mismatched. However, as a teenager who's been living in an otherwise (mostly) deserted version of Eerie for a year, she just gets everything she has by looting the World O' Stuff - so it's meant to look like she's just been scavenging for whatever random trinkets she thinks look cool.
Shawn Hunter on Boy Meets World had clothes that were always badly mismatched (even by the standards of '90s grunge fashion) and at least two sizes too big. It was strongly hinted that his clothes were literal rummage sale rejects, as his family was extremely poor and slovenly. However, he often hid them under a tattered black leather jacket, thereby managing to look somewhat cool.
On RuPaul's Drag Race, the first challenge of every season involves creating a whole outfit out of unconventional materials, such as dollar store junk, curtains, throwaway scraps from a Beverly Hills boutique, etc. Since the contestants have varying design skills, the end result ranges from stunningly elegant to...this◊.
Both Howard and Vince of The Mighty Boosh are this, though they're at opposite extremes. Howard is constantly dressing in plain second-hand looking clothing from the seventies in some hideous shade of brown with a very rare splash of hideous colour, like the purple and orange poncho he wore in series two. Vince on the other hand is a campy fashionista who makes a lot of his own clothes when he isn't buying them from the most trendy shops in London, and dresses in bright sparkly clothes, often with many accessories like belts, a pink hat or bright red cowboy boots. Vince always manages to pull his outfits off pretty well, but Howard, um, doesn't.
This could be considered the Disney Channel house style, at least in terms of very bright, clashing colors.
Macklemore's "Thrift Shop" mentioned a lot of items that considered under this trope (Zebra jammies, big ass coats, and velour jumpsuits, to name a few), which gets subverted into Mundane Made Awesome territory due to the message of the song.
Captain B. Zarr from The Party Zone, who wears a black flight jacket, aviator goggles, a propeller-topped polka-dotted aviator helmet, and white cowboy gloves.
This is universally true, but not for the reason you think. Orks naturally respect the biggest ork around, and since orks grow in size the more they fight, when a Flash Git has more bling, they also tend to be bigger in size to account for all the heads they had to bash in to steal the bling they currently have.
Unless the ork being impressed is also a Flash Git. Then they respect the ork for all his shiny fings.
Although, by that time the other orks the Flash Git lived with have probably kicked him out of their clan for being too snooty, and then they somehow automatically become Freebootaz. It isn't really explained how, nor does anything orky need to be.
Rent. Started a whole new fashion fad trying to duplicate the mismatching East Village thrift shop look, spending hundreds of dollars on what actually only costs $10 to achieve.
To a certain degree, any RPG where the character model changes based on the items equipped will have this going, especially at low levels when character don't have much choice in what's available to them. The Elder Scrolls IV: Oblivion, is particularly egregious about this.
Taken to extremes in the Jak and Daxter series of games: the bizarre half-barefoot footwear in the first game are a particularly notable example. In Jak 3: Wastelander it's shown Jak still wears bandages fashioned like this under his boots.
No More Heroes' Travis Touchdown is no doubt a pathetic enough Otaku to deliberately dress this way. At least the single glove seems kinda handy for using his beam katana, but the rest... the player can choose exactly how ridiculous Travis' outfit becomes by buying more clothes (or diving for shirts in Santa Destroy's many dumpsters), all of them awesomely tasteless Otaku wear.
Fallout, especially the third game, would follow Mad Max and have people with weird attire made out of literal garbage, such as discarded tires.
In Fallout: New Vegas, legionares wear what is obviously sports equipment with odd decorations (including feathers and paper plates). Centurions however show off their badass status by wearing a mishmash of things from enemies they've killed. Including supermutant helmets and Brotherhood armor parts.
The various quest reward gear items obtained between levels 60 to 65 are the most blatant example of this trope as well as the inspiration for the Penny Arcade comic. Mismatched in the most extreme case of garish color clash that could only occur if a clown car exploded in a Skittles factory, the stats on the pieces are still head and shoulders above the most powerful endgame raid gear obtained prior to The Burning Crusade expansion. Many players refer to this phase of a character's life as the pimp suit.
Later expansions have done better, with more unified looking sets... at the cost of sometimes plunging deep into Real Is Brown.
Mists of Pandaria now has Transmogrification, which allows players (for some in-game gold, and with certain limitations) to change pieces of their outfits to match the look of other pieces they have, either averting or invoking this trope as they wish.
From Software's Evergrace duology: the jokey or downright strange looking (calling someone from this series pants-on-head retarded could be disturbingly accurate) weapons and armor, ranging from a frying pan WITH the bacon and eggs still in it, to a bird's nest with the bird still in it (worn as a helmet), to a downed tree (the 'sacred pole', which is about 20 feet long and when not in use is off the edge of the screen), to a random globe you find on someone's desk, to a fanservice-y bit of armor which is just two straps with gigantic pauldrons all megaboost one or more stats. (keep also in mind they can be upgraded and utilized like normal equipment too. The shopkeeper even calls you out on it. "YOU want to upgrade THAT? You're weird.") However, the best all-round builds with an even increase in stats are all plain and generic armor of sorts. And the best full set in the game only looks out of place because this is a medieval fantasy game. (It's a suit of futuristic armor that resembles one of the Armored Core hover leg mechas). Since a good amount of enemies have an immunity to one form of attack or another, using a ridiculous-looking build to Min Max just a couple stats leads to a lot of 0 damage hits on some areas. (An interesting gameplay quirk is that armor that boosts attack doesn't just boost attack, but one of the three kinds of melee attacks too, piercing, chopping, slashing. Whatever is the highest becomes your 'main physical attribute' and determines what is immune to you)
Many male Pokémon characters wear very strange clothing combinations, like pieces of clothing designed for wildly different climates/temperatures mixed together (Gold's heavy sweatshirt and shorts, Lucas' winter scarf and skintight T-shirt in his original design) or highly unfashionable or ridiculous items thrown in an otherwise somewhat sensible outfit (Ethan's knickerbockers that would have been appropriate for a boy his age around eighty years ago but worn without stockings or even socks, Lucas' infamous beret, the thing on Brendan's head). Female characters, on the other hand, tend more towards Stripperific, on girlsfartoo young to be wearing such things. Player characters aren't limited to this, however; Brycen wears what looks like half of a kimono, a mask, and slip-on shoes.
In the case of Gold, his outfit is a real fashion native to the Pacific Northwest where late spring and fall is warm enough for shorts but too rainy for T-shirts, so people usually go in shorts and sweatshirts. So averted for Gold and Red (who just wears jeans and a T-shirt with a short-sleeved coat).
The winner though is Ghetsis in Pokémon Black and White. You simply cannot trust a guy who dresses in what could be a hideously ugly curtain and a castle turret.
A too-short hideous curtain, no less. Something that tacky would have to have been custom-made for him, so why didn't he get it in the right size to fit him and not leave his (equally-garish) bathroom slippers showing?! His outfit in Black 2 and White 2 isn't much better design-wise... but at least it fits correctly.
AZ from Pokémon X and Y is another candidate, but given his size and how he's been Walking the Earth for 3000 years, his dissheveled appearance might be justified.
The Fable series opens the door to this trope by allowing the player to customize the Hero's appearance. Most of the clothes (and tattoos) are parts of sets that at least compliment each other if worn together. If the player chooses to mix and match, though, the results can range from badass to completely ridiculous. Fable II introduces dyes for clothing and hair, which just adds to the fun.
Team Fortress 2 occasionally has shades of this ever since the advent of new unlockable weapons, optional cosmetic items, and the option to paint said cosmetic items. Some players will deliberately design and wear some positively garish things just to stand out. Hot pink and lime green paint applications are popular for this task.
In-universe, the Soldier's 2011 Halloween costume comes across as this, consisting of a coat hanger, cardboard box, plastic cups, dryer hoses, and shoeboxes to dress up as a plausible yet hilariously poor-quality 'robot.' This is in stark contrast to the other classes' costumes, which are all quite clearly well designed in-universe. Justified in that the Soldier is a Cloud Cuckoolander in a state of Perpetual Poverty, so the cheap, unconvincing robot costume suits him. He also makes up for it with unique and priceless vocal responses.
Dragon Age: Origins: Morrigan's initial outfit consists of rags, polished stones, feathers and bits of armor. Justified given she lives in a swamp, so every piece of clothing she owned was salvaged or found.
Tidus, the main character of Final Fantasy X. Most of Tetsuya Nomura's character designs for VII and VIII were at least plausible, but many of the characters from FFX (the aforementioned Tidus and Lulu with her belt-dress being prime offenders) have costumes that are simply strange. Nooj◊, from the sequel Final Fantasy X-2, takes the cake with an outfit that is nothing short of bizarre.
Nomura growing out his more extreme Rummage Sale Reject style can be seen in the progression of the costume designs in the Kingdom Hearts series. Compare, for example, Riku in I and Riku in 3D. Some iconic things like Sora's poofy pants and big shoes may stick around forever, though.
Takako of Iothera makes no attempt to coordinate her clothing.
Cassandra: I know not wearing the entire ROYGVIB spectrum at once is anathema to you, but...
Jericho, of the Whateley Universe, dresses every day in clothes that are so gaudy and so mismatched that people actually get ill from looking at him. He's blind and his psychic vision is black-and-white and uses that as an excuse.
He's specifically picked each part of his ensemble to not go with anything else in order to draw attention away from the crowd he hangs with. That or to fit in with them. Said crowd includes a Lamia, two tetra-armed demonic looking, fear aura packing receptive empath twins, a mute Ancient Apex Predator and an extremely violent current incarnation of the Ultimate Blacksmith. Besides, if he's forced to, he will wear the school uniform. Just don't ask WHICH school uniform...
In Worm, Brian's little sister Aisha is introduced wearing a strapless top too skimpy to pass for underwear, torn denim jeans, and green fishnet leggings.
June from KaBlam! wears: A long sweater that's orange with black spots (think Fred Flintstone), a yellow t-shirt, green plaid baggy shorts, and purple shoes (or cleats in the earlier episodes). If anything, it just makes her even cuter.
Done intentionally with the Freedom Fighters in Avatar: The Last Airbender , who are noted in the artbook to be wearing random piece of clothes they scavenged and pieces of armor they stole.
If you don't know a person like this, then likely, you are that person.
Most Russian soldiers during The Nineties. They even had an ironic rhyme: Форма номер восемь, что спиздим, то иносим (Uniform #8, we wear what we could jack).
Mostly applied to active duty combat deployments, refers to various improvised improvements to standard equipment, scrounged or looted off dead combatants from either side. Popularized due to overly heavy, one size fits all cost cutting solutions implemented in standard issue gear. Examples abound like 32 kg ~= 70 lb flak jacket torso armor, useful against small arms debris and shrapnel, but a useless hindrance in close range urban combat scenarios, due to its inability to stop assault rifle rounds despite its extreme bulk. Desirable item upgrades were quality combat boots, more utilitarian camo (better suited to local climate, lighter, better pattern, improved comfort, improved ergonomic storage), holsters/utility belts/hands free store and carry solutions, lightened paratrooper-issue AK's, squad support weapon-sized extended capacity clips taped together in pairs (for 90+ readily accessible rounds, instead of 20-30), and any manner of light and high-quality sidearms or combat knives. Hence, once so many violations stacked up for utilitarian reasons and improving survival, no one thought anything of small personal touches added for swagger, making for a decidedly mismatched guerrila unit look.
Exception: "demobilization parade uniform". A long-standing tradition to pain-stakingly prepare a ridiculous, customized version with any and all bling (ribbons, patches, decorative elements) and flair they could scrounge and sneak under the radar, to be worn on trip home. Stated goal is to "arrive home in style", but really more of a random reason to get silly and competitive to waste time until discharge, and occupy themselves to make waiting for it a little less difficult.
"Wacky Tacky Day", found at High Schools across the U.S.
Grunge/Punk/Hard rock band the Lunachicks have the tendency to wear outfits like this. At first, it seemed as if it was out of necessity due to lack of a wardrobe budget; later on however, it was very much intentional. Evidence:
See also: the video for "Babysitters on Acid."
Visual Kei artists, bands, and fans, especially those with less money for costuming...or those who want to maintain that "authenticity."
David Tennant himself spends half his time like this, on one occasion wearing a lurid green-gold paisley silk shirt and bright red tartan trousers◊, and on another, a neat white tux jacket, cumberbund, shirt, and bowtie with orange-brown trousers. Another occasion saw him wearing an incredibly bizzare pink and blue brocade tie. His look as the Tenth Doctor is one of his more ordinary looks, apart from a straight up tux or jeans and a normal-looking shirt. Oh, and there's this◊.
Super Junior's 5th album concept ended up looking a lot like this. Hilarity◊ ensued. No, you're not hallucinating. He's really wearing three pairs of underwear under fishnets, two coats, and a tube top made of ropes.
Shite Shirts uses this deliberately, to the extent that you can't even choose a design - you get what you're given.
Country group The Band Perry has been pretty consistently called "An incredibly talented band in desperate need of a better stylist." Their music has been described as "classic Country with an eclectic infusion of Rock, Gospel and Soul." A lot of the time, so is their fashion sense.◊
Japanese street fashion in the decora style, characterized by layered clothing and an artful excess of accessories, can be like this.
At the height of *NSYNC's fame, they regularly showed up to award shows and other functions in hilariously clashing outfits. The Huffington Post even noted being disappointed that they wore simple black suits when they briefly reunited on stage.