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 is for them to purposely use an Outdated Outfit in everyday life.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 1850s. 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. Values Dissonance will often determine how this trope applies: berets are pretty cool in North America, but in France and Spain they are more often thought of as old-fashioned.
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.
See also Gorgeous Period Dress and Elegant Gothic Lolita. If a character's whole personality is stuck in a bygone era, you've got Disco Dan.
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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 nameis stillShowa (aka Emperor Hirohito), not Heisei.
Ryougi Shiki of Kara no Kyoukai wears a kimono (usually light blue) under a bitchin' red leather jacket with fur fringe.
Inverted in InuYasha, with Kagome wearing modern day clothes in feudal era Japan.
Roderich/Austria 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 centurion armor.
America meanwhile still tends to wear his World War II bomber jacket well into the present.
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 ordinarily, 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.
Played with in Fullmetal Alchemist with Alphonse Elric. Though he doesn't wear it by choice, Al walks around in a full suit of medieval battle armor, much to the surprise and commentary of others. Due to his naive, idealistic, chivalrous worldview and nobility (one character even envisioning him as a literal Prince Charming), the armor is surprisingly appropriate, and no one disputes that he pulls it off with considerable awesome, to the point that he is frequently mistaken for his famously talented in-universe Memetic Badass brother Ed. Of course, most people don't realize Al isn't wearing the armor, he's a disembodied soul bonded to it, and the armor is his body.
In Snow White And Seven Dwarfs, which takes place around ~2015, Souichi and Souji wear old-fashioned Japanese-styled clothing. That said, as the revision explains, it's for practical reasons, rather than fashion. They respectively de-age and age rapidly, and so need clothing that's easy to adjust when their body changes (though Souichi goes as far as to wear an appropriate decoration over his ear, so perhaps fashion is a slight factor there as well).
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. Especially the Gentleman Ghost—being a ghost, he's nothing but a walking set of late-19th century finery, with top hat and monocle.
Batman's nemesis The Penguin has sported white-tie-and-tails, top hat, and monocle ever since his first appearance in the early 1940s, when that look was already becoming old-fashioned. He did ditch the top hat and tailcoat in the 1990s, switching to the more practical tuxedo, but even this is on its way out as dress becomes more casual and men increasingly opt for business suits on formal occasions.
The yellow jumpsuit with the black stripes down the sides originally worn by Bruce Lee in Game of Death, but used again in Kill Bill Vol 1. True, it's not exactly "anachronistic", but more "nostalgic" and "intimately associated with its era."
Sam in Benny & 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 dresses in a top hat and frock coat of the sort worn in Victorian times, though somewhat more colourful and gaudy.
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, which hints at her true nature...
By the time of Universal Soldier: Day of Reckoning, the UniSols have forgone the awesome firepower that they're used to, along with the advanced body armour and combat rags, and have gone completely old school. They look less like a professional army, and more like a guerrilla army, with clothing and equipment taken from different time periods, ranging from World War II to Operation Desert Storm. Their weapons even reflect this as well, with lots of Vietnam War Era M16s and AK-47s. Scott 3.0 runs around wearing clothing components from infantrymen in World War II, along with combat boots from The Vietnam War Era. Deveraux himself goes the route of Colonel Kurtz by wearing an M65 Field Jacket, along with matching pants and combat boots.
In Casino Royale (1967), Sir James Bond (David Niven) was a holdover from an earlier, more genteel age of espionage, and underscored it by wearing a series of smart Edwardian suits.
In-universe in The Time Machine (2002), where in 2037, Hartdegen's Victorian outfit, worn because he really is from Victorian times, is praised by a passing woman as being "retro".
In Aunt Dimity Slays the Dragon, when Calvin Malvern describes his King Wlifrid's Faire he specifically says the point of it is to enjoy a fantasy, rather than a stickler-for-detail re-enactment. To that end, he encourages the residents to attend in costume, and lets it be known that anything vaguely like medieval- or Renaissance-era clothing will do. Lori and her neighbours quickly get in the spirit, doing library research, taking one of Sally Pyne's sewing classes, or hiring costumes from a theatrical supplier. Even Bill dons an ensemble from Calvin's stores that he calls a "cool medieval dude" outfit; Lori is particularly taken with the way he fills his tights.
In the Mercy Thompson series werewolves, while immortal, will change their clothing with the clothing style to avoid becoming stuck in the past, while vampires will keep the style of the era they or their leader were turned in.
Willy Wonka's outfit of tailcoat, top hat, etc. brings a classic Stage Magician or circus ringmaster to mind. The book was written in 1964, and with the passing years, it looks more and more anachronistic in both the book and adaptations.
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 Panama 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 tends to end up in situations where his jacket is very out of style - although its most ill-advised outing was to Blitz-era London, as it is actually a WWII German Kriegsmarine jacket. Jack openly mocks him for going around in the Blitz dressing like a U-Boat Captain!
Five really mixed this up with his choice of an Edwardian-era cricketer's outfit combined with (at the time) modern-day sneakers.
Something of a running joke with Ian and Barbara in the First Doctor's tenure - while being both ordinary humans from modern-day Earth, they would pick up various items from their travels, and the Doctor giving them permission to raid the TARDIS wardrobe is a significant point in his Character Development from a total Jerkass into a much more reasonable Eccentric Mentor. As a result, they tend to wear incredibly inappropriate clothing everywhere, usually just for fun, with Barbara usually preferring alien clothing and Ian historical clothing. Barbara spends "The Edge Of Destruction" dressed like a male Thal (from "The Daleks"), Ian wears an ancient Chinese jacket while running around Marinus, and he selects a silly-looking Victorian greatcoat to wear outside in "Marco Polo", insisting he just fell in love with it. The Doctor compliments him on his taste and tells him he got it from Gilbert and Sullivan.
Dodo raids the TARDIS wardrobe (without permission, much to the Doctor's irritation) before her first adventure, set aboard a Generation Ship around the time of the sun going supernova. She spends the whole story wearing Ian's Knight of Jaffa tabard, which both the Doctor and Steven criticise her for - Steven's reasons being because it's inappropriate, and the Doctor's being in case she ruins it and they need it later. In her case, it's less to emphasise her coolness and more to emphasise just how utterly weird she is.
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.). And Jayne, who uses a Lemat Revolver, which would be a very anachronistic Cool Gun in a show set today, is constantly seen in T-shirts and jeans. The best clothes to imagine having in a Western.
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.
It has been speculated in-universe that Jack's fashion sense has a Freudian Excuse of some sort. Owen probably put it best.
In Miracle Day, he attracts the attention of a gay bartender with his signature greatcoat. Yes, he's wearing it while everybody is on a lookout for someone who looks like him (and he's also the only mortal man in the world).
His evil ex-boyfriend, Captain John Hart, favors a '50s-style greaser outfit, cowboy boots, and a Hussar jacket.
The dentist in M*A*S*H 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.
White Collar: Neal Caffrey started out dressing in old-fashioned suits he got from his landlady (they belonged to her late husband, a bootlegger during The Roaring Twenties), but later switches to modern-day suits. However, he still loves hats of that style, to the point where this allows Peter to easily track him down in a foreign country.
Family Matters: Steve Urkel. Although his costume is less "anachronistic" and more "no one outside of a circus would ever wear that."
Kolchak: The Night Stalker: Carl Kolchak's seersucker suit would be vaguely appropriate in the heat of summer in the early 1950s, but made him stick out like a sore thumb in 1975. Darren McGavin once said he figured Carl bought the suit for his first job interview and never bothered getting another.
Supernatural: Many of the ghosts and residents of purgatory are still wearing clothes from the times of their deaths. In addition in the episode "Devil May Care" (S09, Ep02), Abaddon wears a well fitted vintage bus drivers uniform with a billed cap.
The Avengers: Aside from Steed's slightly dated "British gentleman" look throughout, the episode "A Touch of Brimstone" features a bunch of prankster villains, the Hellfire Club, with a taste for 18th century styles.
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!)
King Charles, both in hair and in apparel, tries to reflect late French monarchs. Even on stage.
Once, a singer/songwriter was asked to sing at a nightclub in Los Angeles... in a wig. The long-term result of this was stage persona Prince Poppycock, a displaced fantasy-kingdom noble in richly-colored, embroidered, and trimmed 18th-century costumes, elaborate wigs, and whiteface makeup.
Steam Powered Giraffe. They were voted "Best Costume - Group" in the 2013 Steampunk Gazette Reader's Choice Awards.
Los Romanos of CMLL, Méssala and Calígula, took the soldier thing a little too literally and missed it by a good fifteen centuries as well. Not many complained though.
This is clearly what Thunder Kitty aims for in her outfits, to show how great things "used to be". Opinion is, divided, but in good taste seems to be the general consensus.
Deuce and Domino dressed like Greaser Delinquents out of the 1950s...in 2007. Their female companion, Cherry, wore roller skates - which, while currently making a comeback, are no longer unself-consciously cool.
Apparently, in the 2070s of the Shadowrun world, Steampunk is in-fashion. Not entirely this trope until you remember that a lot of the steampunk look comes from the Victorian/Edwardian fashion of the late 19th-early 20th centuries. Meaning you could have an elf walking down a Seattle street, casually chatting to a friend of his in Berlin via Augmented Reality while decked out in a fine waistcoat, top hat, boots and so-on with an assortment of clockwork mechanisms scattered here and there, maybe even an honest-to-God pocket watch just to complete the look. Oh, and a pair of goggles, naturally.
The villain Retrograde from the Champions supplement High Tech Enemies dresses like an early Victorian dandy. This fits as he has a hatred of modern technology and possesses the power to transform high tech devices into low tech, non-functioning equivalents.
Many clothes of attire in the Fallout series, especially more evident in Fallout 3 and Fallout: New Vegas which cover a wide range of anachronistic clothes for the post-apocalypse, ranging from trenchcoats and 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.
Armor that happens to be modified football armor, no less.
Anachronistic football armor at that.
Several characters in the "Mothership Zeta" DLC can, at least, be justified, as they have just been thawed out from a Human Popsicle state, which they've been in after their abduction. This includes a Combat Medic from World War III, a genuine cowboy from the Old West, and an 18th-century samurai (whom you can't understand) in full battle armor.
The major point of uniform customization in Star Trek Online (assuming you're willing to spend real money). You (a 25th century Starfleet captain) can walk around in everything from the Starfleet uniform of the time to the Earth Starfleet uniform of the NX-01 tour — and that's just the actual uniforms, the off-duty clothing includes the option of 21st century clothing.
Even if you aren't willing to spend real money, the default clothing options includes the TNG movie-era uniform (which is at least two uniform-changes back).
There are even two uniforms that can be acquired that in-universe invert the description of this trope while taking the anachronism one step up: future uniforms.
Tex Murphy in the eponymous series of games dresses as a typical noir-style detective with a trenchcoat and fedora... in a post-World War III world. However, many other characters dress in 30s and 40s styles consistent with the Raymond Chandler-inspired setting.
As part of a promotional with Dragon Age, Commander Shepard in Mass Effect 2 can wear Blood Dragon armour, apparently designed in-universe by an urban combat outfitter to resemble that of a futuristic medieval knight.
Many, many examples in the Soul Series. The most glaring example is Setsuka's alternate costume in IV, which references her European origins but is in an Edwardian style dress. A woman in an early 1900's dress walking around 16th Century Eurasia. Yes, really.
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.
Despite the existence of futuristic city in Noob, anyone not wearing a medieval fantasy style outfit qualifies due to sheer rarity. The recurring hacker was the only character wearing a futuristic outfit up to Season 3.
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.
The Scooby-Doo gang, overlapping with Clothes Make the Legend, are better remembered and mostly appearing in their late 60s outfits. Possibly this is why they came back to them in Mystery Incorporated. Notably, Velma is the only one who's never changed from her orange sweater/red pleated skirt/orange knee socks/red strap-on shoes combo. Shaggy's outfit, however, is probably the one that least needed alteration, although the cultural connotations of it have shifted from Surfer Dude to… well, something a bit less kid-friendly. Then again Mystery Incorporated may take place in some kind of Retro Universe as it seems 60s-70s style clothing is the norm for just about everyone.
The Riddler always had his green bowler hat (which, contrary to what most people think, is from the '60s TV series, not the comics).
The Penguin kept his top hat, bow tie, monocle, and cigarette...although for some reason he let his hair grow a bit longer than you'd expect someone trying to break into high society to do.
In addition to his usual mauve-colored double-breasted suit, The Joker also went around in a boater hat and raccoon coat on some occasions - an ensemble that hasn't been cool since the early 1930s at the very latest.
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 perceived as being notoriously difficult to tie (even though the actual knot is the same you use for your shoes). In an age when many men refuse to bother with even an ordinary necktie, a bow tie is simply beyond the pale.
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. Especially since ninja outfits were invented by someone other than actual ninjas, who dressed as peasants to blend in.
Lampshaded, parodied, yet still works with superhero capes. As well as the short shorts contrasting with the tights' color i.e. Underwear of Power.
In Japanese superhero TV shows (e.g. Super Sentai, Kamen Rider) the pastel scarf replaces the cape (though three Sentai teams have used capes, and Knight and Femme from Kamen Rider Ryuki wore capes as well).
A whole section could be done about this solely about hairstyles, particularly '80s Hair and the duck's ass mullet.
Arguably the entire reason for Steam Punk 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.
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.
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 usually tend to come across as far too colourful and elaborate to have been remotely affordable before the late 19th century.
Exception: The Barong Tagalog, the Philippine National attire for men, is very regularly seen in most formal occasions and government meetings even when the attire itself predates the Philippines's discovery. It was created using thin fabrics and is a very necessary answer to the West's thick and heavy 3-piece suit because of the Philippines' hot and humid weather.
While the traditional kimono as known today (and its variants) can be traced to the late 19th-early 20th Century, its origins can be traced to Chinese-inspired clothing around the Nara and Heian periods.
Cowboy outfits are actually a subversion: Real cowboys in the American Midwest still wear outfits similar to what one would wear during the 19th century (though to what extent depends on the activities they're performing), due to practicality reasons. They often stand out when venturing abroad.
Fezzes. They were the height of fashion in 17th century Turkey; anyone who wears them nowadays is either trying to seem quirky, or just likes the style.note Or, if it's Memorial Day, they're likely a Shriner.
Justified Trope: the Ottoman Empire once wanted to define its culture more clearly, in opposition to Europe's culture. So they picked a style of hat from Morocco, a territory they did not currently own (so they wouldn't be playing favorites), and decreed that the fez would be the official hat of the Ottoman Empire. Europeans wore them when they wanted to be decadent Orientalists. Then it got deconstructed in the early 20th century when Turkey suddenly no longer wanted to be Ottoman, and Ataturk made a famous speech about how rotten the fez was and why Turks wouldn't wear them any more. In short, don't wear a fez if you're in Turkey unless you want to make a very dangerous political statement.
Vic Reeves is basically a clothes horse and so can pull off any style he wishes but he tends to look best in outdated tweed suits, New Romantic outfits with lots of lace round the collar and cuffs, a very frilly cravat and velvet (usually purple) jacket or a waistcoat with almost anything.