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Fashion is fleeting, but style is forever.
Authors want their characters to stand out, and there's various tropes that can be used to make their look distinctive. One such way that says a lot about a character's... well, character... is for them to purposely use an Outdated Outfit in everyday life. Rather than a suit and tie, they'll wear finery from London in the 1850's. Instead of a dress, how about a ceremonial Kimono? Instead of business attire, go to meetings decked out in Renaissance plate armor and helmet. Regional chic from past times works as well: a character wearing cowboy gear is sure to look cool and stand out.
This isn't just a distinct visual look, but a subtle (or very overt) statement that this character is enamored with the bygone style and perhaps even time period. They have a different world view than most contemporary people (though not necessarily the one from their chosen period of dress) and aren't afraid to defy convention by dressing unconventionally. When done well, this trope shows it's not the clothes that make the man or woman, but the wearer who gives what ought to be a desperately out of place Halloween costume a natural style and appropriateness. Somehow, it seems natural that the man in a cowboy suit is opening a bank account, and the woman in the Kimono is working at a particle physics lab, or the man in a bowler hat is slaying zombies.
Anime and Manga
- In Sayonara, Zetsubou-sensei, our main character, his sister, and his devoted stalker all wear old-fashioned kimono. But not just kimono, vintage and seasonally appropriate designs from the early 20th century. The accessories are no exception: the author will knot the obi differently on different occasions, and always matches the characters up with classic outerwear in winter, like Inverness coats and kakusode gaitou. If you know much about traditional Japanese clothing, it can be quite the sight to behold. To be frank, in that universe Japan's era name is still Showa, not Heisei.
- Ryougi Shiki of Kara no Kyoukai wears a kimono (usually light blue) under a bitchin' red leather jacket with fur fringe.
- Inverted inInuyasha Kagome wears modern day clothes in feudal era Japan.
- Inverted in Mushishi, where the main character wears modern clothes in a feudal setting... For no reason other than that it looks cool. According to the author, Mushishi was originally set in the modern day, but they forgot to change Ginko's clothes when the comic changed to the feudal era. And, no, nobody ever says anything.
- Roderich/Austria in Axis Powers Hetalia generally dresses in rather anachronistic suits, among the few constants being a cravat. No one else notices.
- Grandpa Rome meanwhile still manages to look badass in Roman armor.
- Inverted- Miaka and Yui (and presumably the other two priestesses as well) in Fushigi Yuugi were both dressed in their modern day school uniforms. These wouldn't stand out ordanirily, but when you consider that most of the book is set in ancient china, then you get the picture. At one point, Tamahome plucks at Miaka's bra strap and says 'What's this?' Miaka's reaction is to call him a pervert and give him an upper-cut.
- Also when Tamahome is in modern day Tokyo, everybody stares at him as he's in his battle armour, trying to get back to help Tasuki and Chichiri, after finding that Mitsukake and Hotohori have died.
- The Shade and the Gentleman Ghost are both DCU supervillains who dress in old fashioned finery. Justified in that both men were actually alive when these clothes were first being worn.
- The Hellfire Club, enemies of the X-Men.
- The yellow striped jumpsuit originally worn by Bruce Lee in Game of Death, but used again in Kill Bill Vol 1.
- Sam in Benny and Joon is first seen on a train reading a book entitled "How to Dress Like Buster Keaton". He seems to be succeeding at this. (Sam also embodies the other part of this trope, because of his odd personality and fondness for Keaton's style of comedy.)
- Willy Wonka.
- Word of God has it that Mother Gothel of Tangled was intentionally designed with clothing from approximately 400 years before the movie's time period.
- The wizarding world in the Harry Potter films is full of this. The costume designers must have had a field day.
Live Action TV
- Doctor Who: Doctors One (Edwardian academic garb), Two (long coat and bowtie), Three(smoking jacket, ascot, and ruffled shirt with lace cuffs), Five (cricketer's costume and porkpie hat), Eight (frock coat, vest and cravat) and Eleven (tweed suit with leather elbow patches and a bowtie).
- Doctors Four, Six and arguably Seven subverted this trope with bohemian outfits that were never in style.
- Nine and Ten avert this with, respectively, leather jacket and contemporary suits which become anachronistic to their surroundings. Nine dealt with it in The Unquiet Dead, and they travel so much, they'll end up going somewhere where they'll be out of style.
- Five really mixed this up with his choice of an Edwardian-era cricketer's outfit combined with (at the time) modern-day sneakers.
- The Badass Longcoat, especially as worn in Firefly. Practically everyone on the show is wearing clothes from either the 1860s or the early 1990s. Or the Roman Empire, for the Companions.).
- Captain Jack Harkness of Torchwood. It's more subtle than some of the other examples on this page, but he consistently dresses in 1940s style, complete with Royal Air Force greatcoat and suspenders. It's worth noting that his timeframe of origin is the 51st century, so he presumably just likes the style. And when he has to wear more normal and contemporary clothing for a time in Children of Earth, he is NOT happy about it.
- He spends the entire time pouting until Ianto finds replacements.
- It could also be because that's the clothing he met the Doctor and Rose in.
- Seinfeld's Cosmo Kramer wears casual clothing from rougly the 60s and 70s throughout the 90s. At one point, Kramer's regular clothes, while still casual, made it appear to office employees that he was working with them in an office with 90s formal business wear.
- Michael Richards, Kramer's portrayer, once rationalized this by explaining that his character developed a severe case of agoraphobia as a very young man and never again went out to buy new clothes.
- The dentist in Mash loves Japan, so he wears a kimono in his spare time.
- Kyoryu Sentai Zyuranger: The rangers wear color-coded garb from their ancient time when untransformed, and it looks pretty damn cool.
- When not dressed in his Badass Longcoat, Doctor Steel usually dresses in an Aristocratic neo-Victorian Steampunk style, complete with top hat. (He even has his own personal clothier!)
- Steampunk Chap Hop artist Professor Elemental usually dresses in the style of a late 1800's Gentleman Adventurer: khaki shirt and shorts, with a pith helmet and Sherlock Holmes pipe.
- Revo of Sound Horizon, amused by the fact that the fandom decided to crown him king, has taken to wearing ruffled shirts, embroidered waistcoats, cravats, breeches, and other such anachronistic items almost any time he's in public -- and then there's the times he decides to go all out with the Costume Porn...
- Ace Attorney: The Von Karma clan is very partial to the cravat; Miles Edgeworth even has a spare with him after Kay uses it as a hanky.
- Jack Marshall and his late brother Neil wear cowboyesque attire.
- Many clothes of attire in the Fallout series, especially more evident in Fallout3 and Fallout: New Vegas which cover a wide range of anachronistic clothes for the post-apocalypse, ranging from trenchcoat dusters to modern-day riot gear to 1950s parkstrolling outfits.
- Especially the Caesar's Legion in New Vegas. Guess what their entire group decide to wear in the 23rd century.
- While the Final Fantasy series doesn't normally do this, some of the extra DLC costumes in Final Fantasy Dissidia do have some strange costumes as a Shout-Out to either their own games or others. Laguna can wear a knight's armour from his temporary film role in Final Fantasy VIII, Tifa can wear a cowgirl outfit from her days as a mountain guide in Final Fantasy VII, and for the sake of a cross-reference, Lightning can wear Aya Brea's 20th-century jeans and black T-shirt from Parasite Eve.
- Wil of Questionable Content and his "several cloaks."
- Also, the Horrible Revelation, a bar that rents Victorian suits and dresses. (Which appears specifically because the author loves drawing them.)
- And then, when Wil goes to interview for a job at said bar wearing a hilariously outdated suit, he's hired on the spot, and is seen wearing it in every subsequent appearance at work.
- In an episode of Daria, Jane dates a guy who has a thing for dressing up in styles from the early half of the 1900's, and by the end she gets fed up with how seriously he takes all of it.
- Helena Bonham Carter often appears in costumes that resemble outdated fashions.
- The cravat, and possibly the bowtie as well. It's now relegated to formal use since most people find it either too old-fashioned or for stodgy teachers/politicians. Bow ties are also notoriously difficult to tie. In an age when many men refuse to bother with even an ordinary necktie, a bow tie is simply beyond the pale. Major props to people who can actually do them up.
- it's not hard. A cravat(and ascot, for that matter) is tied in the same manner as a regular necktie(sometimes without actually knotting it), and a bowtie uses literally the same knot most people use to tie their shoes(you just have to pay closer attention to keeping things the right length, so that bow will be even.)
- In real life, Zoot Suits never truly went away, so they're not entirely anachronistic, but experienced something of a revival in the 1990s before retreating back to their urban, Black/Hispanic roots.
- Anything to do with ninjas or samurai, at any time, anywhere.
- Lampshaded, parodied, yet still works with superhero capes.
- In Japanese superhero TV shows (e.g. super sentai, Kamen Rider) the pastel scarf replaces the cape.
- A whole section could be done about this solely about hairstyles, particularly Eighties Hair and the duck's ass mullet.
- Zorro costumes are inherently cool.
- Fedora hats, which fell out of mainstream fashion before The Sixties but have lately come into vogue with the hipster crowd.
- On a similar note, thin ties.
- G. K. Chesterton's cape and swordstick.
- Trenchcoats. Add a fedora for good measure. Justified and no longer conspicuous if you're in the rainy season of a rainy climate.
- Of Corsets Sexy.
- Arguably the entire reason for Steampunk fashion, though in its drive to be awesome, it ends up with a fair amount of Anachronism Stew. It's a pastiche of roughly 1850s-1910s fashion, with a generous helping of Sci Fi mixed in.
- Waistcoats and pocketwatches.
- Long, over-the-elbow gloves for women; often called "Opera Gloves" (no prizes for guessing at what event they were worn), these were standard accessories of ladies' costume for evening wear (and often daytime wear) from the late 1880s through the late 1950s; they also showed up in the Regency era.
- Dita Von Teese is the walking embodiment of this trope. The lady is seriously into vintage fashions, especially those of the 1940s and 50s. And it's not just her clothes either; she furnishes her house in 1950s style right down to the appliances, and drives seriously cool vintage cars.
- Tom Waits has not changed his style since he started performing in the '70's - and his style was outdatedly cool even then, as he dresses sort of like a 1930s hobo. Take this '77 performance, for example. The backup band is all in polyester and outrageous mustaches, and Tom looks exactly like he does today, except considerably less wrinkly and more attractive.
- Also a good example is his stint on Fernwood Tonight, a cheesy fake talk show from the '70s.
- Prince and The Revolution did this in The Eighties, in Rummage Sale Reject style. And it worked.
- National costumes from all parts of the world tend to fall into this territory and are often entirely made up in a much later period than what they are supposed to represent, as the national pride rears its head. Needless to say, they tend to be far too colourful and elaborate to have been remotely affordable before the late 19th century.
- The League of STEAM are often written about and interviewed as leading examples of steampunk style.