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- In Attack on Titan, Mikasa constantly wears a red scarf that doesn't quite go with her uniform, because Eren gave it to her to keep her warm on the night that she lost her parents.
- In one episode of Genshiken, Madarame spends the better part of the episode considering the slovenly state of his wardrobe and agonizing over the high cost of stylish clothes. He finally screws up his courage enough to buy some very nice clothes that earn a stamp of approval from The Fashionista of the group. However, at the end of the episode it's revealed that he now wears the exact same outfit every time stylish clothes are called for.
- Kaizaki Arata, main character of ReLIFE, always wears his necktie loose. While he looks like any normal, if a bit sloppy, high schooler, he actually can't tighten it after the trauma of seeing his senpai hang herself.
- In My Hero Academia, Izuku Midoriya, the protagonist, is the only student in his class who hasn't gotten the hang of tying a necktie, appearing as a round bundle around his neck. It ties into his nervous, jittery demeanor and his lack of experience with his superpowers compared to his classmates.
- Meanwhile, Bakugo wears loose-fitting and wrinkled clothes to demonstrate his disdain for authority and lack of politeness.
- Gendo Ikari in Neon Genesis Evangelion has some obvious ones when you examine his clothes. His jet-black outfit is actually a Custom Uniform, but he can't be bothered to button up the front of it. The conspicuous white gloves he wears (to cover some burn scars) obviously don't match the rest of his clothes, and he's perpetually sporting a thick chinstrap beard. It's all meant to show that Gendo is professional but also deeply jaded and doesn't quite care about the overall goal of NERV despite being the guy in charge of it.
- Agent Coulson's suit in the first Iron Man is ill-fitting, in keeping with his role as comic relief. Later movies in the Marvel Cinematic Universe give him better duds.
- Jurassic World: In the very first scene with Hoskins and Owen, we see that both characters carry hunting knives at their backs. The difference, however, is that Hoskins has his strapped perpendicular to his belt, with the handle pointed upward. It would be rather difficult to draw the weapon effectively this way (and downright impossible if, say, his back were to a wall). By contrast, Owen has his strapped parallel to his belt, where he can draw the blade quickly from myriad positions. This illustrates the contrast between the two: Hoskins is an "armchair" badass, pretending to have a warrior's understanding, while Owen is the one with actual, practical experience.
- It's subtle, but in Planes, Trains and Automobiles the viewer can tell that John Candy's traveling salesman character's suit is off-the-rack and made of a synthetic material, especially by contrast with Steve Martin's successful, relatively wealthy character, who wears one made of fine wool that looks custom-tailored.
- In XXX, the title character makes a point of commenting on Milon Sova's bad suit, described as "motel drapes". Later on, we see Sova wearing a better suit, because he's sold information on Xander to the Big Bad - "My government doesn't pay as well as Yorgi."
- In the children's book Bootsy Barker Bites, the main character is a bit of a pushover, and her saggy knee socks are frequently falling down, or are asymmetrical.
- Discworld: In Night Watch, Findthee Swing is impeccably dressed except that his shoes are in bad repair. Sam Vimes notices this, along with his mother's advice to not trust anyone who doesn't take care of their shoes. Findthee Swing is the head of the Secret Police. While Swing looks like a clerk, he's as much of a bastard as any scruffy criminal (like Carcer), and he's also a surprisingly dangerous fighter.
- When Remus Lupin is first introduced in Harry Potter and the Prisoner of Azkaban, it's mentioned that his clothes and luggage bear signs of frequent repair, establishing him as a somewhat shabby and hard-used character. Once he becomes popular among the students, it's mentioned that Draco Malfoy makes fun of his clothes, but no one else cares; thus, the wardrobe flaw helps emphasize Draco's shallowness as well as Lupin's underdog status. It's also an effective contrast to the previous Defense teacher—Gilderoy Lockhart was all style and no substance, while Lupin is the opposite.
- In The Hunger Games Prim's shirt is always untucked. Katniss describes this as resembling a ducktail. She uses this fact to express how innocent and unready for combat Prim would be if thrust into the Arena.
- Curly in Of Mice and Men wears a glove on one hand. The rumor is that he keeps the glove full of vaseline so as to keep that hand soft for his wife.
- The Andy Griffith Show. In "Rafe Hollister Sings", Andy is tasked with trying to make Seriously Scruffy farmer Rafe Hollister look more presentable as he will be singing for a Mayberry social function being emceed by Mayor Stoner, who feels Rafe is far too seedy and raggedy to represent, "The finer things Mayberry has to offer". At one point, Andy does try dropping hints to Rafe to clean himself up, but Rafe's idea of doing so pretty much only consists of an old sportcoat, and tacky tie... while still in his overalls and straw hat otherwise. Later still, Andy and Barney try to outfit him in a new suit himself, however, they are unable to find a suit big enough to fit him, and nearly suffocates in the too small suit they provide for him.
- In Breaking Bad, cancer patient Walter White's (otherwise professional-looking) button-up shirts are always two sizes too big, lending him a disheveled appearance and making him appear scrawny and sickly even when he is in relatively good health given his condition. It also fits his characterization as a very intelligent and competent man who has a bad habit of missing small but crucial details.
- Doctor Who:
- The First Doctor dresses in slightly unusual but rather appropriate Edwardian clothing. The Second Doctor dresses in a similar outfit (supposedly the same outfit), but the clothes are all clownishly large and baggy, his bowtie is perpetually askew and he has an unkempt mop-top hairstyle. When he is put into a machine in "The Macra Terror" that makes him look sharp and gorgeous, he moans about it and immediately resets his outfit to normal much to Polly's displeasure.
- The Third Doctor thinks sharp but inconspicuous dress for a wealthy gentleman in 1970s Britain (or at least a time aesthetically based on it) consists of brightly coloured velvet suits, frilly dress shirts, bow ties and a satin cape. Other characters derisively comment on his ridiculous dress sense, and in "Carnival of Monsters" Vorg even assumes from his outfit that he's a working-class carnie.
- The Fourth Doctor dresses in well-coordinated and obviously very expensive Awesome Anachronistic Apparel with a Byronic or gothic vibe topped with a designer hat, but wears it with a tackily-coloured stripy knitted scarf that is far, far longer than necessary. And never does the buttons up right. And Can't Tie His Tie. And doesn't iron anything. And the hat's visibly crumpled because he tends to just shove it into his pocket. And he rarely even brushes his hair . . .
- The Fifth Doctor dresses in a sharp Cricket outfit . . . with the exception of a celery stalk attached to his left lapel and a pair of sneakers.
- The Sixth Doctor dressed in an outfit which was frequently compared to that of a clown.
- The Seventh Doctor wears mostly somewhat casual formal wear with a hat, beige or dark dress jacket on top of (usually) tartan trousers with a shirt and a tie. He also wears a sweater vest, which wouldn't be an issue, if the thing wasn't covered in question marks. When he shows up in the TV Movie he's ditched it, (and the hat) but he's gone with Albert Einstein's hairdo.
- The Tenth Doctor is nearly always seen in a perfectly-tailored brown or navy pinstripe suit and tie of the sort that would not look out of place in a board room, but with casual Converse sneakers instead of the expected dress shoes to emphasize his eccentric nature.note He even wears sneakers with a tuxedo.
- The Master, when given any choice in the matter, is colour-coordinated and often downright dapper. Even managing this in the usually-ridiculously awful Time Lord ceremonial robes. Granted, it's easy to coordinate if you like to wear predominantly the darker, neutral parts of the spectrum, but this is beyond weird by the normal Time Lord "clashing is a thing" standards. Heck, s/he can even match a fully outfit temporally, let alone culturally. Oh, and yup: considered madder than a bag full of hammers, if brilliant, by most other Time Lords.
- Elementary inverts this twice where Sherlock sees through a character's attempt to appear lower class by their shoes.
- In "You Do It To Yourself" Sherlock and Bell visit a Chinese gambling parlor, and Bells wonders who speaks English. Sherlock points out a supposed janitor who he deduces is the owner, as a janitor would not wear such fancy shoes.
- In "A Giant Gun, Filled with Drugs", Sherlock evades a hit squad disguised as painters, because their shoes do not have paint stains.
- In the Firefly episode "Shindig", Kaylee's idea of fancy dress is a store-bought, ultra-frilly Pimped-Out Dress. She is mocked for her lack of class by the Rich Bitches at the titular party, who favor custom-made and clearly expensive Simple, yet Opulent attire.
- On The Jack Benny Program, Jack shows off his new suit he bought in Hong Kong. He goes on to play a violin duet with guest Giselle Mc Kenzie, during which his cheap suit slowly shreds itself. On radio, Jack was often described as being too cheap to buy any new clothes, wearing ancient styles such as a tuxedo with a belt in the back and buckle shoes.
- M*A*S*H. Radar often wears over-sized and wrinkled fatigues, as well as boots one size too large for his feet. Watsonian: Radar doesn't really dress right for his lack of height. Doylist: Gary Burghoff wanted to distinguish Radar in appearance as well as behavior, and felt such wardrobe would emphasize the character's youthfulness.
- Parks and Recreation:
- For the first few seasons, Andy wears very casual clothing such as sweats, jeans, and T-shirts. In later seasons when he gets a better job and begins wearing button-up shirts and ties, his ties are always tied improperly short, showing that although he is making an effort, he is still unused to dressing up. (A man's tie should always touch his belt buckle; Andy's leave a one-to-two-inch gap.) He also tends to wear ties with short-sleeved shirts, usually considered a fashion no-no. Contrast this with characters like Ben, whose suits always fit impeccably and with a slight nod to current style (narrow lapels, skinny ties).
- Jean-Ralphio attempts to dress in a very stylish and fashion-forward manner, but tries too hard and winds up looking clownish. Compare and contrast with Tom, whose trendy dress becomes a plot point when he rents out his wardrobe to fashion-conscious high schoolers.
- Seinfeld. Jerry invokes this in one episode, when he mentions he is disappointed in an adaptation of Frankenstein he saw, because the Monster didn't wear a blazer. Jerry likes the idea of the Monster in a blazer, on the grounds that he shows he at least makes an effort to make himself presentable.
- In Supernatural, Castiel almost exclusively wears the same trench coat-and-tie combo, with the tie always loosened or even on backwards, demonstrating that he is unconcerned with (or completely clueless about, Depending on the Writer) human customs.
- Final Fantasy VII:
- It's hard to tell due to the PS1-era polygons, but Rufus Shinra appears to be wearing an incredibly large and baggy white business suit immediately after his promotion to President, like a boy trying on his father's clothes. In later appearances he is more of a Man of Wealth and Taste.
- Cloud's SOLDIER uniform is about half-accurate - the clothes are right, but unlike the symmetrical, sleek armour favoured by most members, it uses quirky, industrial-looking asymmetrical light armour apparently modelled after motorcycle parts, bandages and mismatched accessories. It oozes a very 90s manga kind of cool and suits an out-of-work mercenary living in a Cyberpunk slum, but the effect is to make him look a bit scruffy and crazy, as if he'd desperately cobbled together something that looks a bit like a SOLDIER uniform out of bits and pieces that other people have thrown away. Besides being almost certainly the literal truth, this is a pretty straightforward metaphor for what is going on in his head.
- Street Fighter EX: Cracker Jack wears a shirt with tie, a Nice Hat and blue trousers. Except that, being a thug, his shirt is sleeveless and his tie is tied directly on his neck. EX2 has him become a proper Sharp Dressed Man, though.
- In The Legend of Korra, Mako wears an old scarf at all times, even when dressing to the nines for a fancy date, because it's one of the few mementos he has of his parents. Something of an Informed Flaw; although some characters react to it as though it clashes horribly with his fine clothes, to the audience it looks perfectly normal, even stylish.