Somebody needs to disguise their identity and/or avoid attracting attention. Their solution? Wear a Black Cloak with a really big hood. Because nothing diverts attention away from oneself better than a big creepy black cloak that makes you look like the Grim Reaper. Its hood will cover their face in shadow, regardless of whether it's long enough to actually do so. In addition, the hood will never fall off accidentally, even if the wearer is fighting a Wind Mage in the middle of a typhoon. In modern times, a hoodie is a good substitute.
Yes, wearing a hood during a fight isn't a good idea because it constricts your peripheral vision, but who cares as long as it looks cool? Besides, being mysterious is badass. Even more besides, no one has peripheral vision anyway.
Video game designers of older days liked the trope because throwing an all concealing hood (or suitable replacement) over an unimportant or "mysterious" character meant that they could skip on actually animating the character's speech.
This can be a Justified Trope if in a Wretched Hive or Bad-Guy Bar, where this is a perfectly acceptable fashion accessory.
Contrast with the Cool Masks worn by superheroes, which disguise them by making them look more conspicuous. When not, see Malevolent Masked Men.
The members of the Black Valley in Mai-Otome wear these; once it's revealed they're not evil, it gets lampshaded when there's a little girl in the group, wearing a cloak and a hood and a pink bow over the hood.
March Story has the title character with a hood that droops down past his neck.
In Death Note, Light uses this once, with a hoodie (rather less conspicuous than most hoods).
In Claymore, Clare wears a hooded cloak while infiltrating the Holy City of Rabona. She however has the sense to wear a dark cloak as a form of camouflage at night. Seven or so years later Clarice and Miata do the same but in broad daylight. It did not work out very well for them.
Oddly enough, the Seven Ghosts frequently wear these as well. Of course it is obvious they are being mysterious, but they seem more concerned with avoiding positive identification.
Fakir wears a hood to cover his distinctive green hair while he wears a mask in the tenth episode of Princess Tutu. This is probably in part because Fakir has a tendency to be a little theatrical when it comes to his role as the Knight.
Subverted with Korumi in Onegai My Melody - Not only does her black hood disguise nothing, but the second season reveals it's apparently genetic.
Holo from Spice and Wolf wears a hood to cover up the animalistic wolf-ears on top of her head. She switches over a less-conspicuous hat, however.
She switches a lot between the two. The point of the hood is to imply that she is a traveling nun, explained in the light novels to be the standard getup of any independent woman who wants to do traveling, and as such doesn't normally get a lot of attention. The hat on the other hand is a part of a typical city girl outfit, which is more convenient when she wants to go drinking and having fun, activities unsuitable for even a nun out of convenience rather than devotion.
When on an assassination mission, Guts from Berserk wears a dark cloak with a hood. He's also seen wearing his all black hooded cape post-Eclipse after he becomes the Black Swordsman.
Turkey from Axis Powers Hetalia wears a hood and a mask, when he isn't the Ottoman Turks (Where he wears a mask an a huge hat instead).
Roderick Kingsley, the original Hobgoblin in Spider-Man, has a hood. More often than not, it casts a shadow that hides most of his mask while leaving only his glittering red eyes visible. Very creepy. When he temporarily gave up the role, his successor kept the hood but never produced the shadow, just one of many many ways he was a failure. Eventually Kingsley came out of retirement, killed him, took the role of the Hobgoblin back, and sure enough, lots of creepy shadows.
Raven of the Teen Titans loves the Hood; it somehow conceals her face just as well as a mask but without that pesky glue. It even stays on when she flies. (The cartoon provides a possible explanation for this by giving her telekinesis, a power she lacks in the comics.)
In the comic book version of W.I.T.C.H., the girls wore brown, hooded cloaks to be able to walk around undetected in Meridian. In their human forms. Notice that we're talking about the comic version of Meridian here, were everyone is green-skinned, has tentacle hair, or is otherwise downright monstrous looking. For some reason, it worked.
As his name suggests, Hooded Justice, the first costumed adventurer in the backstory of Watchmen, wore a hood- a black one that covered his entire face, meant to resemble an executioner or hanged criminal. The resemblance to a Klan hood was not accidental.
The Oliver Queen Green Arrow during the Mike Grell series The Longbow Hunters and the following Green Arrow monthly series (1980s and 1990s run) wore a hood. Dinah "Black Canary" Lance designed it for him so he wouldn't catch a chill in Seattle's rainy clime. Since he had abandoned his trick and gadget arrows for broadheads instead, it was a better fit for a darker and grittier GA than the old "Robin Hood" hat from the Golden Age. Initially he still wore his domino mask underneath the hood, but after enough people explain they already knew who he was he gives up the mask and wears only the hood. Depending on the artist, it still hid the face—it was the beard that defeated the whole purpose of it all.
Subverted in The Traveler. While the Traveler always wears a hood, it's constantly falling off and he's shown putting it back on numerous times per issue. He wears a mask that covers everything but his eyes and mouth though, so his face still isn't seen even when the hood is down.
Skroa used this in Book 7 and 8 of Les Légendaires to conceal his identity. Partially justified, as his real appearance is a giant, green, anthropomorphic bird-like demon, meaning any disguise would be better than just going around as himself. Ironically, this was actually of little use, as the only person he showed himself to in the arc died a panel later, and the protagonists instantly recognized him when confronting him at the end.
Time Trapper, the mysterious purple wearing X-factor villain in Legion of Super-Heroes wears one. But since his identity changes all the time it doesn't matter when S/He takes it off.
The main villain of Doctor Who: Prisoners of Time wears a hood to hide his identity, as he can't let the Doctor recognise him before their first chronological meeting. He has another reason for the hood as well: he's former companion Adam Mitchell, who was left with a hole in his head when the Ninth Doctor expelled him from the TARDIS for bad behaviour.
In the Harry Potter fic Rise of the Wizards, Harry's account manager sent him a note which mentioned that Gringotts' nighttime customers tended to be of the more... disreputable sort and suggested that Harry "would not look out of place with a hooded black cloak."
In the Death Note fic Welcome To The Family Light Yagami determines that not even the genii of Wammy's House can withstand the mighty stealth powers of the "magic hoodie" that somehow renders him unrecognizable whenever he goes out to do nefarious things.
Magnus Bane in City Of Bones wears a hooded long coat when he sneaks in the Institute to heal a mortally injured Alec Lighthood. Jace dons a few hoods himself while investigatin cough-stalking-cough Clary. Clothing of choice of all the Silent Brothers.
The Star Wars movies both avert it and play it straight. The Jedi almost always shed their hooded cloaks before a battle. Both Palpatine and Anakin (though he isn't hiding his identity, he briefly fights with a cloak on) use this straight.
Obi-wan Kenobi wears a hood that hides his face at his very first appearance, making him look like a mysterious scary thing that causes the Sandpeople to flee. This was probably what determined the Jedi cloaks and hoods would become standard issue.
Luke wears a hood for a while in Return of the Jedi when he's dealing with Jabba and playing the mysterious scary Jedi.
Aragorn in The Lord of the Rings is first seen with his hood pulled up indoors, with only the light of his pipe illuminating his eyes. It's supposed to be ambiguous as to whether "Strider" is a good or bad guy at first. The evil Nazghul also wear hoods.
Cthulhu (2007). The protagonist sees a line of Black Cloak hooded figures coming across the bridge towards him, and is so freaked out he steals a boat to avoid them.
Subverted with Hot Fuzz. The ominous hoodies seen occasionally and hinted at as possible suspects are just local kids raging against authority via minor vandalism. And when you consider what that authority is doing...
The Alchemist in Vidocq wears a black hood over his mirrored mask. Very creepy, since when a victim to be tries to glimpse under the hood, they only see their own face staring back.
The Mountain Man in the third Cold Prey film hides his face under a hood.
In Kenneth Branagh's 1989 film of Henry V, King Henry wears a hooded cloak to disguise his identity when he goes among his soldiers the night before the Battle of Agincourt.
When not invisibly causing "accidents", Sharack's ghost in Superstition appears as a robed and hooded figure.
Forgotten Realms' Drizzt Do'Urden rarely wears the hood on his cloak unless the sun is particularly bright, though if he's going somewhere he never has before he at least tries to keep it up in the hopes the gate guards will be stupid enough not to challenge a hooded traveler.
Lampshaded in the Discworld novel Going Postal, in which the antagonist notes that running through dark and rainy streets with a hood and cloak is the surest way to attract attention and quietly orders a subordinate killed for his incompetence.
In Guards! Guards!, Vimes notes the same thing, albeit it without the kill orders.
Vimes: "There are probably countless perfectly innocent reasons to stand in front of a secret society's recently destroyed headquarters while wearing a black robe and cowl and muttering to yourself. Perhaps I should ask him to name just one..."
Defied in The Wheel of Time: Myrddraal, the second-most common type of Shadowspawn, could easily pass for a human by wearing a dark hood. As a result, in several countries, the law states that everyone wearing a hood is to be killed on sight, just in case. In less watchful countries, this is not the case. Aes Sedai use this trick all the time to hide their trademark "ageless face".
Night's Dawn. Quinn Dexter adopts this trope deliberately to awe his Satanist followers and enemies, using his powers as the Possessed to make the hood particularly dark. The reader can tell he's lost his temper whenever his face makes a sudden reappearance.
The eponymous "Ghost Jogger" of the short story in Nancy Drew Ghost Stories makes full use of his hood to hide the fact that he's a young man assumed to be dead at the beginning the series.
In the Ranger's Apprentice series, the eponymous Rangers are well-known throughout Araluen for their ability to melt into the forest and move without being seen. The prevailing superstition is that their cloaks are imbued with magic, allowing them to turn invisible. The real reason? Part of it is that the cloaks are camouflaged, with a large hood to completely conceal the wearer's face in shadow. The other part is that due to his training, a Ranger can stay perfectly still and hidden even when the enemy is looking right at them. From any farther than a few meters, a Ranger in hiding literally blends into the surround forest.
Done in Stargate SG-1 by, believe it or not, General Hammond. He was on Chulak tracking down Teal'c to help save the rest of SG-1.
Overdone in the 2006 BBC Robin Hood: soldiers never inspect people wearing hoods.
Justified in 2008 Merlin: Morgana creeps around in a hood, but all the soldiers already know she is a princess and obey.
Superhoodie of Misfits wears a hood, but uses a ski mask, and later a paintball helmet, to actually hide his identity of Simon from the future as the hood fits pretty tightly over the top of this head and therefore provides no shadow.
The Cape from, well, The Cape used to use a hood for a disguise, until it almost revealed his identity. Now he has a mask on underneath the hood.
Angel did this in an episode while sneaking in to spy on Darla and Drusilla, as they had a meeting with many vampires and demons.
Arrow definitely follows this trope. Avenger-of-evil Oliver Queen's entire concept of hiding his identity is painting the area around his eyes dark green/black and pulling the hood up. It's amazing that his ex-girlfriend and mother don't put it together when he converses with them face-to-face. Consequently, he isn't known as Green Arrow, but the Hood.
This hood has been worn by his first mentor Yao Fei, and passed to his daughter Shado before Oliver wears it.
Spectre plays with this in his webseries and novel first apperances. His gaming avatar is wearing a face-concealing hood, but his identity get revealed (to those who read the novels) when the curosor donning the name of a retired Living Legend appears over his head at the end of his battle against Ystos.
Game Masters just have a hood big enough to hide their face in the webseries, but the comic gives them shorter hoods and faces hidden in shadow except for glowing red eyes.
The Season 1 quest givers and the Soullesswho are actually the same group of people have this for pure identity concealing purposes.
AJ Styles as part of his entrance attire, although he pulls it up as he comes out, unlike most examples.
Lay Cool did this in WWE, which some critics took to be a "take that" toward AJ Styles since they also tended to wear similar shades of blue and Michelle McCool used the Styles Clash (a move AJ invented on accident and since became his most famous finisher).
CM Punk wore hoodies during his entrance from late 2012 to 2014. Occasionally he'd wear the official Gracie hoodie.
Of course, professional wrestlers do it because it is common in combat sports. Unlike wrestling, this is done to block out distractions, such as a roaring crowd, as you make your entrance, rather than to give people a distinct look to remember or make your entrance more elaborate. In both actual competition and simulated competition though, athletes may wear heavier clothing, hoods included, so as to stay warmed up and not get stiff before the game/performance starts, as that can lead to injuries.
In Darksiders and Darksiders II both Death and War have this trope well. War in his standard form and Death in his reaper form. Also the character Draven who helps Death in the Kingdom of the Dead has his vision impaired by a cloak.
In Bully, Jimmy walks around in a ninja suit. Instead of getting him in more trouble, this makes him less noticeable. You could start a fight right in front of a prefect, and nothing happens.
Magus of Chrono Trigger adopts this as part of his "Prophet" disguise. Since the sprites are virtually identical to his normal appearance, albeit with a hood, this counts as a Paper-Thin Disguise.
Gorath from Betrayal at Krondor often wears his hood to conceal that his identity from people who'd want to kill a dark elf like him, people who'd want to kill him, personally, or both. Justified, since his long ears are his most striking feature to the casual eye, and a hood does hide them well.
Hector, Lyn, and Eliwood in Fire Emblem: Blazing Sword, while trying to hide their identities as marquesses in an enemy country. From the same game we also have Ephidel, who uses his cloak to partially hide his unnatural appearance.
Done again in Path of Radiance with the laguz, but this time getting bumped into by a stranger knocked down Ranulf's hood and revealed his Unusual Ears. Unfortunately resulted in an angry mob.
In various entries to the series, male Manaketes appear as cloaked, hooded figures. The females, meanwhile, are typically cute young girls.
The main character of the Thief series. Of course, everyone who needs to know who Garrett is already knows anyway.
Bloodline Champions has a hood for the male Seeker outfits, one for the male Stalker outfit, and one for the officer Thorn outfit.
The MUD Shadows of Isildur is guilty of this- just putting up your hood allows you to disguise everything but your build and the color of your cloak.
Ezio Auditore da Firenze, the protagonist of the second game, has a similar hood. Actually his outfit's amazingly similar to Altaďr's, just updated to fit with 15th Century Italian aesthetics. Amusingly, in that era and setting a hood like that is very conspicuous compared to the large hats almost everybody else is wearing, so it's most likely out of tradition.
It does keep his face hidden though, which given his status as a wanted criminal is something he's not exactly going to leave exposed, as evidenced by the Notoriety system.
Oddly enough, in Brotherhood the Notoriety system does not apply until you do the Sequence 3 Core Memory where you help the Thieves Guild, which can be done last if the player so chooses — and story-wise, Ezio and Claudio became notorious for something that's way less extreme than what Ezio pulls off earlier in the story (like dragging a Borgia captain out of his guard post and into a fatal collision with a nearby wooden scaffold).
Averted with Altaďr and Ezio's modern-day descendant Desmond Miles, who wears a hoodie but has yet to be seen with the hood up. Although presumably he may later as he now has all of Ezio's skills. It should also be noted that said hoodie is white, just like traditional Assassin costumes from the past.
It turns out that the hood is slightly pointed, just like his ancestors' "eagle beak" hoods.
Desmond finally puts his hood up in Assassin's Creed III, when he goes to the skyscraper and the stadium for the artefacts that will let him enter the Temple, and the Abstergo building he was held in in the first game to rescue his father.
Ezio's nemesis, Rodrigo Borgia, also wears a stylistically similar, but black hood. Until he upgrades to Papal vestments, anyway.
Also, Il Lupo, AKA The Prowler, is a Templar agent trained in the skills of the Assassins. Fittingly, his outfit is very similar to Ezio's, though black and red rather than white, and his hood is missing the distinctive point.
Connor keeps the tradition during his timeline. Since it's during The American Revolution and a large part of the world is snowy, his hood keeps his head warm.
In "The Tyranny of King Washington" DLC, Connor wears a wolf skin instead, which also ends up looking like (really strange) hood.
Edward Kenway gets a hood early in the game when he takes them from the body of a man who tried to kill him. Most of his outfits after that also have the hood. Not the two Armor of Invincibility, though. Which makes it amusing when his animation still has him pulling up the hood that isn't there.
Almost all the assassins you meet along the way also have hoods. The one exception is James Kid/Mary Read, who talks a lot more and whose ability with disguise is more important to the plot.
Mickey's hood is actually altered to accommodate his ears... Which sort of defeats the purpose of having a hood conceal your face in the first place. "Who's that small person with very large, noticeable, visibly circular ears?" "Hmm, I don't know, it's a mystery!"
Averted with Sora, whose outfits have hoods that are never worn over his head (except in one artwork...). His hoods in his first two are instead used to hold Jiminy Cricket and his journal.
Kairi also has a hood she never wears (KHII), but it's a heck of a lot less noticeable.
That Man from Guilty Gear certainly qualifies. Even in the boss battle against him, his hood never falls off even when hit by a Tyrant Rave.
The Hunters from Left 4 Dead wear hooded shirts, and are appropriately enough the stealth experts of the Infected. It also helps hide the fact that they have no eyes
Weavers in Loom wear hoods that completely conceal their face except for their glowing eyes. (They look like Jawas; since it's a LucasArts game, this may be a Shout-Out.) An in-universe myth says that it's fatal to look beneath a Weaver's hood; Cobb can't resist testing it out when he meets the main character. It's true.
In inFamous, the first gang of the game, the normal Reapers wear red reaper style hoods while the Conduits wear white. Oddly enough, they normally paint a skull onto the hood itself. The hood happens to hide their face, no matter how much light is actually shining on it. Then again, they aren't entirely human according to later missions, so maybe they just have pitch-black faces.
In Prototype, the main character, Alex Mercer, wears a hood to cover his face. This is because the real Alex Mercer was wearing a hood on his way to Penn Station because he was on the run. In the game, Alex keeps wearing that hood because thats what he was wearing when the FBI shot him dead. The Blacklight Virus simply copied his appearance at the time of his death and made it his Shapeshifter Default Form.
Caster in Fate/stay night though it's really not entirely clear as to why. It's clear she's a beautiful woman but she isn't really distinctive enough for it to identify her. Nevertheless, you only get one good look at her actual face. Perhaps it's to make sure the audience thinks of her as a manipulative witch and saves the reveal of her rather elfin features for when she gets all her sympathy points and won't need us to pity her anymore since she's already dying?
The entire Kaka clan, including playable character Taokaka, from BlazBlue wear yellow hooded jackets that conceal their entire face, revealing only glowing eyes and a fanged mouth.
Platinum the Trinity wears one that obscures the top part of... their face.
Amusingly played with in World of Warcraft. There are several types of hood, but about 70% of them don't cast any shadows over the face. About half of what is left is composed of larger hoods that also don't hide faces. Hilariously enough, most of the hoods that actually do cast shadows over the face are intended for priests, and when examined with the rest of their matching gear sets, seem to have been made with holy priests in mind.
There's one for warlocks too.
Generally, the baddies hide their faces behind scarfs, though.
Death Knights start with a face-concealing shadowy hood.
Face-concealing scarves are mostly reserved for rogues, Defias Brotherhood, and the Syndicate. Enemy rogue NPCs are pretty rare and Defias and the Syndicate are fairly low-level enemies. Once you hit level 40 or so, there's nary a scarf in sight. A lot of hoods in Outland and Northrend, though. Pretty much every cultist and many of the spellcasters wear hoods.
Princess Zelda wears a hooded cloak for the majority of The Legend of Zelda: Twilight Princess. Subverted in that it only conceals her identity for about 2 minutes, before she herself reveals herself to Link.
The semi-human "Habnabits" in Ferazel's Wand wear full-length cloaks with the hoods always up, shadowing their faces except for two features: large, vaguely human eyes, and a snout like an anteater. They're the good guys, though, as signified by the fact that their cloaks are a wide variety of colors rather than the generic black.
While a few robes and cloaks in Dragon Quest IX include hoods, they are typically shown folded back instead of actually being pulled over the wearer's head; certain helmets are the only hoods the player character can actually wear. Played straight, however, by the wandering ghost Serena, which ironically makes her stand out.
The White Mage class in the Final Fantasy series have hooded robes, but whether or not they wear the hoods is variable—there are exceptions, but the general rule of thumb, as seen in Tactics, FFIII, and FFV, is that male White Mages tend to wear the hood down, while female White Mages tend to wear the hood up.
Particularly young or cute white mages (or related classes) may get a hood with cute cat ears on it. N'awwwww.
In Final Fantasy IV: The After Years, Kain runs around in such an outfit and is thus referred to as the Hooded Man. Precisely why he is disguising himself, asides from giving the player a meta thrill, is not gone into.
Dark Kain has made him an internationally wanted criminal. always a good plan to be disguised after that.
Tokugawa Ieyasu in Sengoku Basara 3 wears one, though it doesn't obscure his face. Considering his look and moveset is based off boxing, it could be due to this.
The various unnamed Reapers in The World Ends with You, who bar your path with invisible walls, forcing you to complete tasks for them to proceed.
And now there's a Pokémonbased off a mohawk hoodie. Scrafty's hood is made up of the shed skin of its pre-evolved form. Slightly subverted as it doesn't really wear the hood during battle, but they are fighting-type Pokémon and described as "hoodlums", so they have the attitude befitting the trope.
In a level of Ultimate Spider-Man, Peter has to spring into action when his costume isn't available to him, so he just puts the hood on his jacket over his head.
The enemy Re-class battleship in Kantai Collection apparently has her hood up for the look of it; you could hardly miss a girl wearing a scarf, a bra, a half-open coat, and a knapsack, with a tail that has its own mouth.
Annyseed On page 19 we see that the sinister Coldsteem has adopted a hooded costume.
The Order of the Stick: Donning the hood of his green cloak is apparently all that's needed for Belkar to use his Hide skill. Examples include #107 and #469.
Miko Miyazaki wore a hood in her first handful of appearances, allowing for a Samus Is a Girlmoment when it was knocked off.
In Homestuck, hoods (or god-hoods) are a standard part of the clothing of those who have ascended to the God Tiers. They vary significantly in design - a Seer's is a normal hood, but a Knight's is a close fitting coif, while a Witch's is split and looks like a pair of stockings. Some are even more abstract; a Bard's isn't even a hood but a conical hat.
Duane from Unsounded actually has a very good reason to constantly wear a hood. A galit, the glamour that keeps Duane looking human is broken by eye contact. So, in his case, being unhooded would actually draw more attention to himself. And mobs.
Androssi, Akryung and Rachel during their introduction in Tower of God.
In El Goonish Shive, Noah wears this along with a Black Cloak to conceal his identity as the one fans refer to as the "The Child Left Behind". It helps that he seems to be able to literally cloak himself in shadow too, obscuring almost all details other than his shape.
In the webserial The Descendants, the character Occult wears a hood that magically covers her face in shadow. Subverted due to the fact that under the hood, a glamour makes her look Nordic instead of Hispanic. So what's the point of the hood?
So that if someone manages to pierce her disguise, they still wouldn't see her face? It's unlikely they would think of the possibility that the revealed face was a fake as well.
Todd in the Shadows is constantly—you guessed it—shrouded in darkness, which makes the hood a bit of a redundancy but also gives him a very unique look. The hoodie actually hides nothing out of the shadows, though, so in his own videos if he's required to be out of the darkness his back is to the camera. In crossovers, he wears a black piece of fabric completely obscuring his face from the nose up, eyes included.
The servants of Lord Inglip wear distinctive red hoods when receiving their master's commands.
Raven from Teen Titans wears an outfit that includes a blue cape and hood. She's not disguising her identity, though, because that's a bit hard to do when you have purple hair and a big red gem encrusted in the middle of your forehead. Nor does she seem to have a problem being seen with her hood down in public places, either; it's just part of her superhero chic.
In Teen Titans Go!, her hood is ALWAYS up. The only episodes she is seen without her hood are in "Laundry Day" and "Meatball Party".
Kenny from South Park has his face permanently obscured by a hood. Voice too, though apparently none of the main characters have a problem understanding him. In a few episodes, as well as the movie, we've been permitted a glimpse of what's underneath, but he definitely belongs here. He also adopts a face-obscuring hood when disguised as Mysterion (or at least one that hides his hair).
The evil Daedalus from The Mighty Hercules, who usually ends each episode being dragged off by said hood.
Stripperella. When supervillain Queen Clitoris first makes an appearance she's hidden under a hood, solely so Stripperella can make the inevitable Double Entendre.
Miss Martian from Young Justice occasionally wears a stealth outfit that includes a hooded cloak. She usually doesn't wear the hood up unless she's using her camouflage powers.
In The Smurfs: The druid leader in "The Smurf's Time Capsule", and Nemesis, who wears a hood over his face because it's so scary to look at. He will even remove the hood to show his face in order to scare his victims into submission.
And if you walk into a bank wearing a hood, you will probably have a chat with the police.
In the US some businesses at high-risk for robbery (liquor stores, gas stations/convenience stores, banks) have a sign on the door stating "Hoods or face obscuring headgear must be removed prior to entry", or some variation.
An partial example occurs with this in regards to medieval executioners and their hoods. They were usually depicted in contemporary art as bald and pox-ridden or scarred, but never with hoods. The association probably came about due to the fact that after the English Civil War, no one wanted to execute the king, so the executioner disguised himself with a black hood in order to protect his identity, and later on pieces of art made this standard even in settings where it would have made no sense.
Which is how the poker player Phil Laak got the nickname, "The Unabomber," because he always wears a hoodie and sunglasses similar to Ted Kaczynski. He wears them to make it harder to read his facial expressions.