Awesome Anachronistic Apparel/Playing With

Basic Trope: A character is wearing an outdated outfit, but still manages to look really cool in it.
 * Straight: A character is wearing a kimono and hakama in a modern day setting, and manages to look quite stylish in it. The other characters don't seem to notice or care.
 * Exaggerated: A character is wearing a kimono and hakama in the distant future, and manages to look quite stylish in it. The other characters don't seem to notice or care, despite every other character wearing futuristic clothing.
 * Justified:
 * The character is old-fashioned, and his clothing helps reflect this.
 * Alternately, he's a time traveler. Or Really Seven Hundred Years Old.
 * Inverted:
 * A character is wearing a kimono and hakama in a modern setting, but he can't quite pull off the look, and is made fun of by the rest of the cast.
 * A character is wearing a futuristic outfit in feudal Japan.
 * Subverted: A character is wearing a tuxedo in the Arthurian era, except it turns out he's just an actor out of costume inspecting a movie set.
 * Double Subverted: That same character then goes to a beach town, where he lives, still in the tux.
 * Parodied: One character wears clothing from a different century and region every episode.
 * Deconstructed: The character is deeply unstable and has no idea what time period they're really in.
 * Reconstructed: But despite that they manage to look completely awesome in it.
 * Zig Zagged: A character is wearing a kimono and hakama in the present day, but it turns out to be a costume he's wearing in a play. But then gets out of his costume and puts on his zoot suit...
 * Averted: All characters wear time-appropriate clothing.
 * Enforced: "Put him in an old-fashioned outfit, it might look good on him."
 * Lampshaded: "Why the hell is the sergeant dressed in a kimono? I know it looks great on him but we're in the middle of a freaking war here!"
 * Invoked: A teenager tries wearing a kimono and hakama in the present day to make a fashion statement.
 * Defied: A character's wife has to force her husband to dress in modern clothing, despite everyone else thinking he actually looks pretty good in his outdated outfit.
 * Discussed: "Never thought I'd see someone wearing something that old. But admittedly, he looks pretty good in it..."
 * Conversed: "Style doesn't just disappear because fashions change, say a guy walking down the street wearing a great billowy cloak would still look pretty good."
 * Played For Laughs: A time traveler goes to modern times wearing a Roman suit of armor and is reminded that this is the wrong era for that. He then proceeds to change into several other outdated outfits; although he looks cool in every one, he still stands out, until he finally remembers which century he's in.
 * Played For Drama: The character's outdated outfit is supposed to represent how he's a "fish out of water". This eventually leads to the character finding out he's actually from the time period his clothing represents, having been brought back from the past as a baby.

Put on your bolo tie, and head back to Awesome Anachronistic Apparel.