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Awesome Anachronistic Apparel
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 is for them to purposely use an Outdated Outfit in everyday life.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? 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. Wait, what.

See also Gorgeous Period Dress and Elegant Gothic Lolita. As a general rule, any costume emphasizing the Most Common Super Power will be this. When it fails, you've got Disco Dan.

Examples:

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.

Film
  • 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.)

Live Action TV

Real Life
  • The cravat.
  • In real life, they never truly went away, so they're not entirely anachronistic... but Zoot suits 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, any where.
  • 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 80's 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.