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Outdated Outfit

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Fashion is merciless. It beguiles kings and makes them slaves. It should come as no surprise that in the space of years (if not months) a perfectly fashionable dress or suit can go from tres chic to horrible; what is surprising is when someone keeps wearing said outfit... for over fifty years!
No, this is not the White-Dwarf Starlet, but rather a character who is identified with a type of outfit (or just one) and have kept the look for far too many years without getting an update. This is common in Comic Books where the story is set in the "Present Day" and the clothes become hilariously anachronistic.
If they ever do get some new duds, expect much poking fun at their hilarious past fashion sense, while said character adamantly maintains the look is "still cool!" and it's the world that's out of touch. On the flip side, if the outdated outfit has become an intrinsically linked part of the person's image, it can lead to fans crying that they should have stuck with the old clothes.
See also Grandfather Clause. Compare Awesome Anachronistic Apparel, where a character's clothes are so cool that, while they may be out of fashion, they are certainly never out of style.
See also Unintentional Period Piece and Popularity Polynomial. I Was Quite a Fashion Victim is what happens when a character does move on and is horrified by their previous costume. Refugee from Time is a similar phenomenon applied to a character's backstory or origins, while Disco Dan is this but applied to a character's whole personality.
Contrast Fashions Never Change and No New Fashions in the Future.
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Daughters of the Dragon: Misty Knight still wears a poofy 1970s-era afro (weirdly, though, it's far more exaggerated than her actual style in the '70s). Luke Cage, on the other hand, has managed to get his shirt buttoned all the way up.
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In-universe this occurs in the film The Toll of the Sea. Lotus Flower is a young woman living in China during the early 1920s. When she presumes her American husband will take her home with him, she tries to dress her most fashionable in Western clothes. Alas, she uses her grandmother's old fashion book for advice. She looks gorgeous, but still painfully out-of-date by several decades.
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X-Men:
Jubilee is the most extreme example that comes to mind. Although semi-possible as an outfit that a young girl would think is "cool" in the 1980s, the bright yellow trench coat and wrap-around sunglasses became just plain painful as the '90s continued. She did have a more modern costume during her time with the New Warriors.
Gambit's costume, with the wrap-around headpiece and leather jacket over actual body armor look, is now becoming a very dated 90s look. It doesn't help that almost all of the other X-Men have gotten a costume upgrade over the years except for him.
Dazzler; it doesn't help that she was created to cash in on the disco craze. And in 1980, when disco was running down. Dazzler wears her 1970s costume these days, though. Apparently, her singing career got a revival, so she's all glam again.
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Black Canary's outfit dates back to her debut as a 1940s noir-esque villain. It has been replaced but the comics always come back to the original. It's been given several explanations over time, with the most common being that the Legacy Character daughter of the original styled herself after her mother's old outfit. In the 2010s, DC explained her outfit as being because she's in a rock band.
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The Simpsons:
Disco Stu and his leisure suit.
Otto in later seasons. He dresses and talks like a perpetual 1980s teenager. He even still wears a portable cassette player on his hip despite the fact that they've been obsolete for years.
The Simpsons had intentionally outdated designs even by 1980s standards but it becomes more blatant as the seasons go by.
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The main character from Hard to Be a God (written in 1963) wears nylon underwear. In the 22nd century.
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Captain Peacock of Are You Being Served? is always seen wearing semi-formal morning dress, which had long been abandoned by all but the staunchest businessmen, even in The '70s. This goes hand in hand with the character, who is fastidious, pompous and stuffy.
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In Echo Chamber, Tom wears a patterned sports coat and bowtie on a date. There was speculation that this was a Shout-Out to Doctor Who, but Word of God has it that Tom bought the jacket only because he thought it was hideous.
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Spirou is perhaps the ultimate incarnation of this trope: When he started in 1938 he was a bell-boy elevator operator in a chic hotel wearing the traditional red outfit. The outfit (especially the hat) has become tied with the character, even as bell-boys in general and elevator operators in particular were consigned to history. Most readers ended up not knowing what the hell Spirou's uniform came from, but changing it became problematic because it was so intrinsically tied with the characters. Thus Spirou wore his outfit for many decades despite it being out of place. Newer authors compromised by making Spirou wear a variety of red clothes, and only keeping the uniform's hat to be used occasionally as a Continuity Nod. Many characters have even remarked on the odd hat's appearance or even outright questioned where it's from. Of course, it's lampshaded in Le Petit Spirou where every single member of Spirou's family wears the outfit 24/7. Recent takes on the series justify the clothes in different ways: in Emile Bravo's version for example, Spirou is a bell-boy operator but the reason he wears the outfit all the time is that he's too poor to buy new clothes. Meanwhile, Fantasio's fondness for bow-ties remains unexplained throughout the series.
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Supergirl wears a skirt because she was inspired by Otto Binder's earlier creation Mary Marvel, who in turn was inspired by female figure skaters. By the late 60's, though, a skirt-wearing heroine was seen like outdated, leading to debates among comic fans who think a skirt-wearing flying female hero is stupid and impractical, and fans who point out that her skirt costume is iconic at this point, she usually wears shorts underneath -thus denying the fanservice angle-, and super-hero costumes are not practical anyway.
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In The Beano, the artists occasionally tried to 'update' the characters' clothes. It usually didn't take (as with The Bash Street Kids and, to some extent, Dennis the Menace), but subtler changes did (as with Roger The Dodger getting long trousers).
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Mad Men covers the entire span of The '60s but that doesn't mean that every character gets a new wardrobe according to every years' new trends. The older characters wear the same outfits from The '50s or The '40s like the three-piece suits of Roger Sterling and Bert Cooper, or the early 20th century shirt with cameo brooch wore by Jurassic secretary Ida Blankenship. Even the gorgeous Joan Harris sticks for most of the show to her Marilynesque wardrobe when it's becoming outdated in the late 1960s (she does eventually upgrade her style in the last seasons).
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Invoked in Mortal Kombat 11. When several of the original Kombatants are plucked from the 90's in the time travel plot, most of the characters are wearing what they wore in the older games...except Johnny Cage, who is dressed in hideous 90's day-glo and not the subdued karate pants with no shirt that he actually wore in every Mortal Kombat up until MKX. This could be due to Johnny's personality having been massively flanderized since MK9.
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Shantae has a variation with Rottytops; she wears a sweat band, tank top and daisy duke combo in what is an Arabian-inspired setting, never mind the first game coming out in 2002note It was originally planned to be released in the 90s., yet Rottytops' wardrobe has stuck with the series since then, even after other characters got design changes.
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Invoked in Nurse Betty. The title character believes she's a nurse on her favorite soap opera hospital, and the most surefire sign that she's out of place is the fact that she's wearing the little white nurse dress and cap while surrounded by actual nurses wearing modern blue scrubs.
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The Wizarding World in Harry Potter tends to be between a couple of decades and a couple of centuries out of touch with Muggle fashions, alongside regularly being clueless about the gender-appropriateness of muggle clothes, leading to an Anachronism Stew hodgepodge of clothing depending on the age of the wizard and how much stock they put in holding themselves apart from mere Muggles. Wizard fashions change with the times as well, as illustrated in Harry Potter and the Goblet of Fire. Ron comments on his Yule Ball robes, "Traditional? They're ancient!"
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The notion of this became a running gag on Arrested Development, with the character of Lupe who was known to wear exclusively hand-me-downs from Lucille. This usually resulted in funny background gags, such as a Halloween jumper on Thanksgiving or a Bush/Cheney jumper in late 2005.
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Assassin's Creed: Valhalla: In a guest appearance in a crossover storyline, Kassandra is dressed in a Roman legionnaire's uniform... while on 9th century Skye. It helps show that Kass hasn't gotten much socializing done lately, because her modern day appearance had her in a suit.
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Some attempts to modernize her looks became dated almost right away. See her headband in the 80's and her belly shirt in the 00's.
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While not as pronounced as others here, Garfield's owner Jon has hair, a collar shirt and shoes that firmly put his creation in the seventies. Given his Disco Dan tendencies and general social ineptitude, not to mention Vague Age, this actually suits his character quite well.
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It's been mentioned more than once that Nephandus of the Whateley Universe dresses like it's the 80's. The 1880's.
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Dazzler; it doesn't help that she was created to cash in on the disco craze. And in 1980, when disco was running down. Dazzler wears her 1970s costume these days, though. Apparently, her singing career got a revival, so she's all glam again.
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The James Bond of the novels has a pretty good sense of timeless style, except for the nylon underpants.
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Mortadelo y Filemón: According to Word of God, Mortadelo's clothing was already outdated when the comic was started in The '50s.
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Captain Jack Harkness of Torchwood fought in World War II, and has worn his military greatcoat ever since. On occasion, this has caused other characters (who are unaware that he is immortal) to speculate that dressing in period military means he's gay. (Of course, he's not that picky.)
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The Story Between a Dumb Prefect and a High School Girl with an Inappropriate Skirt Length: Sukegawa dresses and acts like a sukeban from the 80s or 90s, before any of the characters were born. None of them except Izubuchi recognizes her long skirt and fingerless gloves as signs of delinquent fashion.
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Popeye:
Popeye gets a pass when wearing his Navy whites (which haven't changed much in decades) but usually he's wearing a much more dated nautical outfit that was old-fashioned even in the 1930's.
Olive Oyl's fashion statements hasn't changed since the 1920s with her psyche knot note a bun hairstyle mimicking the bobs of the decade. and galoshes.
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Several examples: Donald Duck's sailor suit, Big Bad Wolf's one-suspender-trousers and Cat-in-the-hat-hat, Daisy's bow, and so on. Admittedly, both Donald and Scrooge's outfits were supposed to be outdated from the start. Attempts to modernize them (as in Quack Pack) have been made, with mixed results. At best. Part of this is caused by a schism of canon among the comic writers: some of them consider the stories to still be set in the 40s and 50s while others insist that they take place in the modern world.
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In Who Framed Roger Rabbit, despite living in the mid-twentieth century, the humorless and villainous Judge Doom wears a suit years out of date, complete with a black hat, overcoat, gloves, and sword.
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ECW's Tommy Dreamer drew an enormous amount of hate in his early days due to being a prettyboy face (good guy) and his comically outdated wrestling outfit, complete with bright green suspenders.
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Blade: Blade wore some really gaudy outfits back in the 70s, which tended to be red, or yellow coats with green pants. His modern look tends to be much more appreciated.
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Swedish military-humour character 91:an Karlsson still wears a blue uniform (outdated already when he was created in the 20s) despite most his comrades having switched to more modern camo.
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In Fans!, Rumy's family is so old-fashioned that they may as well live in the 19th century. Her sister in particular could give Mr. Burns a run for his money as far as an inability to comprehend what people are into these days, and she's never seen out of a kimono.
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In the Cheburashka cartoons, Shapoklyak's outfit is very fashionable... for The '30s.
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In Milo Murphy's Law, time-travelers Cavendish and Dakota decided that since every time period they went to was the past, they'd go with a Seventies-style of dress. Dakota went with the 1970's, while Cavendish went with the 1870's.
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In The Owl House, as Belos/Philip prepares to return back to the human realm, he changes into his normal human clothes... That is, normal clothes for a guy from the late 17th century. Luz lampshades this.
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In Thoroughly Modern Millie set in 1922, flapper Millie tries to get her new friend Dorothy to change her old-fashioned long dresses for short skirts and bob her equally olf-fashioned long hair.
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Lampshaded in The Venture Brothers: The titular brothers (and even their father) dress in a mostly 60s pulp fashion. Same goes for Dr Orpheus (who dresses like Dracula, for lack of a better term). All of them have had their outdated duds remarked upon by people who avoid the trope. Dean and Hank have both remarked that their fathers forces them to wear those painfully out of date clothes. They'd much rather wear something more...normal.
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Very conspicuous in Andy Capp where every character's outfit (and the whole scenery surrounding them) is stuck in the late 50's- early 60's. This doesn't stop them from using smartphones in the more recent strips.
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Plot-relevant in Good Bye, Lenin!. As stated below under Real Life, this happened in the Communist bloc. The entire movie is about tricking protagonist Alex's mom into thinking Communist Germany still exists after the fall of the Berlin Wall. Thus, everyone who is going to visit Alex's mom is required to take off their Capitalist Germany clothes and put on their Communist Germany clothes.
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 Good Bye, Lenin!
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Gambit's costume, with the wrap-around headpiece and leather jacket over actual body armor look, is now becoming a very dated 90s look. It doesn't help that almost all of the other X-Men have gotten a costume upgrade over the years except for him.
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In Avatar: The Last Airbender, the Northern Water Tribe plans to infiltrate the Fire Nation Navy and assasinate Admiral Zhao. They use actual Fire Navy uniforms for the infiltration, but since they were captured 85 years ago during the early part of the war they are blatantly out of date when compared to the modern uniforms. Sokka, who traveled from the Southern Water Tribe and encountered many Fire Nation soldiers along the way, has to explain the differences in styles. The 'old' uniforms are based on the designs from the original unaired pilot episode.
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The Flash: Barry Allen was associated with a bowtie long after they were popular. With his return, Geoff Johns has Barry explaining that he had to borrow an old bowtie on the fly for a court appearance where he met his future love, Iris West, for the first time. She liked the look. He said nothing.
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A downplayed example, but Ralphie still wears his red baseball cap in The Magic School Bus Rides Again. Kids still casually wear caps however it's largely seen as a nineties (or rural) fashion.
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Blondie (1930): Dagwood Bumstead once commented to a man on a park bench about how many "weirdos" were walking around the city. That man couldn't help but notice that Dagwood wears a suit with one giant button on the front of it. It's a single shirt stud in a particularly stiff, formal shirt meant exclusively for white tie and tails. It's not meant to be worn with anything else, and is all but extinct even there, with most modern formal shirts taking two or three studs. (The high-waisted trousers and mandatory waistcoat worth with white tie mean that the four-stud shirts used with tuxedos don't really work.)
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In Grand Theft Auto: Vice City, Tommy Vercetti spent fifteen years in prison, and the shirt he wears went out of fashion. Other characters in the game make puns on this.
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At one point in The Red Green Show, during a discussion of Dalton's driver's license (expired in 1994), Mike comments that his wardrobe suggests 1962.
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Mary Jane Watson is a huge victim of this, being a fashion model during her appearances in the 1980s and 1990s. The funny thing was that the contemporary "big hair" look that Todd Mc Farlane gave her in the 1990s actually dated more quickly than her "so outdated it's cool again" 1960s hairstyle, which was then brought back.
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Fallout: "Pre-war" outfits are clearly 50s fashion despite that the war happened in the late 21st century. This is a major clue (among many others) that the game takes place in an alternate universe — the game is stuck in the 50s, mostly to afford the zeerust.
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 Fallout
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9 Chickweed Lane - for a comic that's supposedly set in the present a lot of the characters dress in a style more suited to The '60s or The '70s (turtleneck shirts and dresses for the ladies, tweed coats with elbow patches for the men).
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In I'm Gonna Git You Sucka former pimp Flyguy was sent to prison in The '70s and when he gets out a decade later he wears the same outrageous pimp outfit he wore before his arrest: yellow suit with wide leopard print fur trimmed bell bottoms, a wide brimmed hat and clear platform shoes filled with water and goldfish. Instead of looks of admiration as he expects people they point and laugh, making fun of him. At the end of the movie he changes into a cooler (for The '80s) outfit: a slick, silk grey suit and fedora.
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Superboy Conner Kent's leather-jacket, colorful outfit, piercings and surfer cut were meant to make him look cool and modern... in the 90's. He has updated his look a couple of times since then.
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Back to the Future:
Back to the Future Part II: In the alternate 1985, where Biff is a Corrupt Corporate Executive, Biff and his gang (still together since 1955) seem to fit in◊ more with The '70s than The '80s. Part of this is because Biff's look and lifestyle are based on Elvis Presley's final days. Biff's outfit and hairstyle in the original 1985 in the beginning of the first movie also seem more at home in the 1970s.
In Back to the Future Part III, when Marty travels to 1885, Doc Brown from 1955 dresses Marty in what he believes to be appropriate period themed garb. Marty protests the loudly colored faux cowboy clothing, saying "Clint Eastwood never wore anything like this". When Marty gets to the past and goes into town, he's quickly mocked for his clothing and nearly gets killed by the bad guys. When 1885 Doc Brown saves him, he asks "What idiot dressed you in that outfit?" Marty says "You did.".
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Red vs. Blue downplays this with Caboose. While everyone else has upgraded to Halo 3 armor and weaponry, Caboose still has the defaults from Halo 1. Anyone not familiar with Halo would just think he has a custom helmet. Caboose's antiquated and more primitive choice of gear actually becomes a plot point later on in the storyline.
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This becomes a plot point in Somewhere in Time. Richard procures what he thinks is a period-appropriate suit when traveling back in time only to arrive and find out that it's ten years out of date. Then, when he tries showing off how practical his suit is, he accidentally discovers a modern penny, which snaps him back to the modern day.
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S.H.I.E.L.D.: Dum Dum Dugan's trademark derby hat was already old-fashioned for his social class and nationality during World War II.
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In Back to the Future Part III, when Marty travels to 1885, Doc Brown from 1955 dresses Marty in what he believes to be appropriate period themed garb. Marty protests the loudly colored faux cowboy clothing, saying "Clint Eastwood never wore anything like this". When Marty gets to the past and goes into town, he's quickly mocked for his clothing and nearly gets killed by the bad guys. When 1885 Doc Brown saves him, he asks "What idiot dressed you in that outfit?" Marty says "You did.".
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When Marnie Was There seems to take place in the 2010s but the titular Marnie dresses in very vintage looking clothes for a 12 year old. Even her colours of choice are somewhat dated. Her parents and their peers also dress in clothes that look more like they're fit for the early-to-mid 20th century. This is because Marnie is a ghost and is fashioned after her childhood in the mid-1900s.
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Phoenix Wright: Ace Attorney takes place 20 Minutes into the Future and Miles is wearing a ruffled cravat as if it was the Victorian era, although this seems to be something common to the Von Karma family he's from, and Phoenix has made snide comments to himself about his ruffles.
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The original design of the First Doctor's costume was intended to deliberately invoke this trope, as the combination of out-of-fashion clothes and mixed eras effectively gave the impression of an alien traveler from another time who would have only a broad idea of mid-twentieth-century fashion. (This can be viewed as counterpoint to other sci-fi time travelers who turn up dressed spot-on for the moment of broadcast, such as Gary Seven in the Star Trek: The Original Series episode "Assignment: Earth".)
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Archie Comics:
Jughead's hat was actually in style for High School boys in the late Thirties/early 1940s. In The '90s Jughead got a backwards baseball cap. Fortunately the Powers That Be decided to change his hat back, given that he was named after it. The more modern-looking reboot keeps the hat, however the show Riverdale replaces it with a similar looking beanie.
Miss Grundy from the earlier strips had a dress with silhouettes akin to the mid-1920s. A strip from the 1970s even joked upon her hemline.
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Oliver of the The Brady Bunch, when he appears in nobody had to die is described as a "Baby John Lennon" (with the long hair and the round glasses) and the unnamed narrator describes his apparel as the product of a bygone era. She still wants to protect him, though.
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Tintin:
Tintin's plus fours. Tintin himself was slowly updated (he wore jeans instead in his last adventure, Tintin and the Picaros). Herge once received numerous letters pointing out a minor inaccuracy he made in a depiction of a certain airplane, and wryly asked why he wasn't receiving similar mail over Tintin's pants being decades out of fashion.
While Captain Haddock's jacket, turtleneck and naval cap are pretty much timeless and Tintin's plus fours were something people actually wore at the time of his first appearances (less so after World War II, though), Professor Calculus' stiff high collar was outdated from the start. Like the beards sported by many of Hergé's scientists and savants, it harkens back to the time before World War I.
Additionally, the Thompsons have tried a few times to blend in when investigating in a foreign country, but their outfits were often too "folkloric", and on at least one occasion, the national dress of the wrong country. Far from blending in, they've been known to attract crowds come to laugh at them. Nowhere more hilarious than in The Blue Lotus, where they come wearing Qing Dynasty clothes, complete with queues and fans!note They were also holding their canes behind their backs as they walked down the street, making it all the funnier. The result?note which provides the page image for Overly Stereotypical Disguise
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Parodied in Futurama, in the episode "Less Than Hero", where Fry and Leela gain superpowers and, together with Bender (who already has them), decide to become superheroes; as Captain Yesterday, Fry wears a decidedly outfashioned white-and-blue disco outfit.
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Scooby-Doo.:
Freddy's orange ascot.
Pretty much everyone's outfit really! Daphne and Velma look incredibly dated when not wearing more modern duds. The only one that could be said to have avoided it is Shaggy, and he's only avoided it out of luck — pants and a t-shirt just refuse to go out of style. Although Shaggy's pants were originally (that is, in the 1969 series) drawn bell-bottomed, so not even he is entirely safe. In the 1980s stories with Scrappy, the bell-bottomed ends were gone, inexplicably gaining a red shirt in the process, though later they were changed to brown again.
It's lampshaded in a commercial for What's New, Scooby-Doo?, in which the gang finds Fred's lucky ascot. As the gang tries to figure out what it is, Fred has a flashback to the time he wore it last and got made fun of by a girl at a party. Velma then deduces it may have been worn around the neck, at which point Fred dejectedly says he's going to wait in the van. The ad had this tagline:
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It's lampshaded in a commercial for What's New, Scooby-Doo?, in which the gang finds Fred's lucky ascot. As the gang tries to figure out what it is, Fred has a flashback to the time he wore it last and got made fun of by a girl at a party. Velma then deduces it may have been worn around the neck, at which point Fred dejectedly says he's going to wait in the van. The ad had this tagline:
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Back to the Future Part II: In the alternate 1985, where Biff is a Corrupt Corporate Executive, Biff and his gang (still together since 1955) seem to fit in◊ more with The '70s than The '80s. Part of this is because Biff's look and lifestyle are based on Elvis Presley's final days. Biff's outfit and hairstyle in the original 1985 in the beginning of the first movie also seem more at home in the 1970s.
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Most of the girls in Peanuts usually wear typically 1950s-style dresses. (Lucy and Sally eventually started sporting slacks, but kept their coiffed '50s hairdos.) A late strip makes reference to Harry Potter but the kids still dress like it's the 1950s, 1960s at the latest.
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Steve Rogers in The Avengers (2012). His fashion is hopelessly out of date (long-sleeve collared shirts, maybe with the sleeves rolled up and slacks) which makes him look stuffy and formal compared to Tony or Clint. Entirely justified, given that Cap spent the last 70 years as a Capsicle. Cap himself suggests that his old stripes and stars uniform is a bit old-fashioned. Coulson suggests instead that with everything that has happened, people "might need a little old-fashioned." This noticeably changes as of Captain America: The Winter Soldier and beyond where Steve adopts a more modern haircut and wardrobe to symbolize him becoming more acclimated to the present day.
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In the second season of Stranger Things, students of Hawkins Middle School and Hawkins High School in 1984 wear plaid, long skirts and fashion that came out of The '60s. In "MADMAX", the scenes went from two girls walking with short-sleeved vests and long plaid skirts to a girl wearing a turtleneck and a plaid skirt. There is also a girl with '80s Hair and a plaid, long skirt walking down in a hallway full of students.
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Good Omens (2019):
Angel Aziraphale's coat is centuries old and visibly worn out, but he keeps wearing it because he's fond of it.
Anathema frequently wears old-fashioned dresses.
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 Good Omens (2019)
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El Goonish Shive's Elliot, Tedd and especially Justin have very 1990s/early 2000s hairstyles. They've been toned down as part of the Art Evolution, and Tedd eventually got an Important Haircut that changed it to a less dated style, but Elliot and Justin's haven't gone away completely.
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Beetle Bailey still wears the standard Army uniform that was used between the late 40s and early 70s.
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Doctor Who: The Doctor. This is forgivable, though, since if their outfit isn't fashionable in one episode (or era), it may be in style in the next one.
The original design of the First Doctor's costume was intended to deliberately invoke this trope, as the combination of out-of-fashion clothes and mixed eras effectively gave the impression of an alien traveler from another time who would have only a broad idea of mid-twentieth-century fashion. (This can be viewed as counterpoint to other sci-fi time travelers who turn up dressed spot-on for the moment of broadcast, such as Gary Seven in the Star Trek: The Original Series episode "Assignment: Earth".)
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 Doctor Who
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Johnny Thunder of the Justice Society of America sported a green business suit and bowtie that would have been in fashion when the character was created in the 1940s, but he kept wearing it for decades afterwards. The narration in one story in the 1980s lampshades this by mentioning that his fashion sense went into a permanent stall sometime in the 1950s.
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The Wire: After spending the last 14 years in prison, Cutty shows up to an interview in a double-breasted sports coat, obviously having not updated his wardrobe since he got out.
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Daredevil: Typhoid Mary originally wore outfits based on New Wave Music. In the 2000s, this was replaced with leather.
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Superman:
Jimmy Olsen sometimes still wears a blazer and bowtie. Poked fun at in All-Star Superman, when Jimmy is voted worst dressed man in Metropolis. In that series, he also takes a shine to "Kryptonian Overpants". This trope changes depending on the decade, as blazers and bow-ties have gone in-and-out of style since Jimmy's debut.
Superman himself. The "shorts over tights" thing was actually the outfit worn by athletes in the early 20th century and heavily associated with circus strongmen. So the "classic super-hero look" is actually over a century old. (And ironically the way that spandex outfits are sometimes worn with shorts brings the whole trope full-circle, with reality becoming fiction becoming reality again.)
Supergirl wears a skirt because she was inspired by Otto Binder's earlier creation Mary Marvel, who in turn was inspired by female figure skaters. By the late 60's, though, a skirt-wearing heroine was seen like outdated, leading to debates among comic fans who think a skirt-wearing flying female hero is stupid and impractical, and fans who point out that her skirt costume is iconic at this point, she usually wears shorts underneath -thus denying the fanservice angle-, and super-hero costumes are not practical anyway.
Some attempts to modernize her looks became dated almost right away. See her headband in the 80's and her belly shirt in the 00's.
Superboy Conner Kent's leather-jacket, colorful outfit, piercings and surfer cut were meant to make him look cool and modern... in the 90's. He has updated his look a couple of times since then.
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Jimmy Olsen sometimes still wears a blazer and bowtie. Poked fun at in All-Star Superman, when Jimmy is voted worst dressed man in Metropolis. In that series, he also takes a shine to "Kryptonian Overpants". This trope changes depending on the decade, as blazers and bow-ties have gone in-and-out of style since Jimmy's debut.
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Scooby-Doo and the Cyber Chase:
The gang's clothing was updated (and carried over to What's New, Scooby-Doo?). It had a hilarious comparison between present updated Daphne and her old-style Video Game counterpart:
Fred and his counterpart, on the other hand happily reminisce on the relevance of the ascot.
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John Steed in The Avengers (1960s) wears a bowler hat and old-fashioned suits, to match his classic cars and generally old-fashiond style. His partner, Mrs. Peel, by contrast wore very up-to-date (for the time) Mod fashions and drove an also modern for-the-time Lotus Elan.
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Buffy the Vampire Slayer:
Certain vampires are identified by their old-style clothes. (One of the more hilarious examples was in "Faith, Hope and Trick", where Faith is first seen dancing with a disco vampire.) Joss Whedon originally intended all vampires to wear clothing matching the time period in which they died, but realized that the concept was major Nightmare Retardant. The first episode had a passing reference to the idea, with Buffy identifying a vampire based on his 1980s fashion.
Spike has been using the same leather jacket since he looted it off of Nikki Wood in 1977, and has had the same bleached hair since at least before Billy Idol, seeing as it's been mentioned in canon that Billy stole his hair from Spike.
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Ric Flair became so associated with his long sequined robes that he continued using them in his entrances decades after they went out of fashion.
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Mother Gothel from Tangled has a wardrobe centuries out of date, which serves as an indicator that she's far older than she appears to be.
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1.0
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 Tangled
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Monica's Gang: Usually you can tell in which decade the character was introduced by looking at their outfits. The girls that were introduced from the 60's to the 70's wear dresses (except for Denise, who debuted in the 80's, but her default outfit is a puffy-sleeved dress with Mary Jane shoes), whereas the ones from the following decades wear tees and shorts; Likewise, the boys from older decades wore loafers and suspenders on their pants, whereas the ones from the younger decades have sneakers and cargo shorts. While the older characters can wear modern-style clothing for merchandising or if the plot calls for it in the comics, their default attire is always stuck in the 60's. This also applies to their parents.
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Schoolhouse Rock! has a lot of those characters fall victim to this. The superhero Verb in his mirrored shades and shirt open to his belt really stands out. Not to mention all of those bell-bottoms!
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Ghosts in The Frighteners seem to be stuck wearing whatever outfits they died in. This means that Stuart is wearing a letterman jacket from the 1950s, and Cyrus is trapped dressed like Disco Stu, which he is unhappy about. Averted after they cross over to heaven, at which point they get some nicer white duds.
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In Star Trek: Voyager, the crew of Voyager are lost in the Delta Quadrant before the rest of Starfleet changed their uniforms, leading them to continue wearing the old-style uniforms, even after re-establishing contact with Earth.
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Spider-Man: The Amazing Spider-Man (Lee & Ditko) was especially bad for this. Seeing almost all the adult men wearing fedoras, teenage boys wearing bow ties, and girls wearing long skirts are especially jarring by today's standards.
Mary Jane Watson is a huge victim of this, being a fashion model during her appearances in the 1980s and 1990s. The funny thing was that the contemporary "big hair" look that Todd Mc Farlane gave her in the 1990s actually dated more quickly than her "so outdated it's cool again" 1960s hairstyle, which was then brought back.
Supporting character Captain Jean DeWolff dressed like someone out of a 1940s film noir and drove a matching vintage roadster, but that seems to have been a deliberately retro look.
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Goemon Ishikawa XIII of Lupin III is known for wearing traditional samurai garb (even down to the Fundoshi) in the modern era, as well as claiming that the modern Japan has lost touch with the spirit of the samurai.
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This is actually done for people who know their fashion history in Downton Abbey, where Grande Dame Violet, the Dowager Countess, wears outfits from the 1900s in the 1910s and 20s, while her granddaughters and daughter-in-law (and her sister-in-law, a forward-thinking American) wear the height of fashion.
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The following is a list of statements referring to the current page from other pages.

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Costume Tropes
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Signature Tropes
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Stock Jokes
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