The typical Hollywood perception of wearing glasses is that they are nerdy, homely, or otherwise undesirable in various ways.
These ways could include the "sex appeal" department, and it could also include the strangely instantaneous deletion of glasses from the face of any up-and-coming character in fiction shows. Depending on your personal preference, this could be part of an Unnecessary Makeover. Always the first step in a Makeover Montage. The vision problems that presumably required them to wear glasses in the first place are seldom addressed, but if it's a long-term change, they might make some mention of contact lenses at some point.
Pretty much, if "the glasses must go," then the example must go here.
A common step in a Beautiful All Along transformation. Also see The Glasses Come Off, when the glasses are ditched so the character can be more Bad Ass. Recently, an "Evil Through and Through" variation has started occurring in anime, where hidden villains remove their glasses to show that... well, yes, they are beautiful all along, but they don't have to hide their intentions anymore.
Some people really do find glasses sexy in real life, and thus get a little annoyed when this happens, considering it an Unnecessary Makeover. There is even a large following specifically for this in fiction, and of course there are plenty of pornographic websites dedicated to people wearing glasses that can be found without much effort.
A common way to avert this one is to turn the character into a Badass Bookworm. Contrast with Meganekko and Sexy Spectacles.
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Inverted in a series of Dutch commercials where 'unsexy' people where turned into deadsexy people by giving them glasses.
And this becomes a plot point multiple times. Whenever Kyon needs to tell the difference between an alternate-reality Nagato or the one he knows, it's either used as a motif or a definite emotional encounter for Kyon - the one he knows no longer wears glasses. Also, it proves useful during "Bamboo Leaf Rhapsody", when Kyon meets a past version of Nagato who doesn't know who he is yet - she's wearing glasses; when she turns out to have the ability to "synchronize" with her future self, and thus downloads her memories of him, she takes off her glasses without prompt, thus informing Kyon that this is his familiar Nagato.
Her unprotected eyes then become Kyon's means of judging her mood and hence the danger level of the current situation. He gets called out on this by Clingy Jealous Girl Haruhi because he's paying too much attention to somebody other than herself.
Aizen gives up his glasses when he reveals himself to be the true villain in Bleach, in this case going from Hidden Villain to full-out Badass.
Likewise, Quattro from Magical Girl Lyrical Nanoha seemed to be a goofy Dojikko villainess at first, but abandons her glasses when she reveals just how ruthless she is. Likewise Due, upon abandoning her disguise.
Ordinary maid Emma from Victorian Romance Emma turns out to be gorgeous when she's persuaded to take off her glasses and dress up for a ball. Unfortunately, this being the age before contact lenses, she can barely see a thing.
Ouran High School Host Club does this when Tamaki first removes Haruhi's glasses, revealing her large, bishonen-style eyes. The host club insists she wear contacts from then on, as her eyes are apparently a draw for female customers. Flashbacks reveal that she only recently wore the glasses in the first place and normally wore contacts — the glasses were only a temporary thing anyway.
Miu Fuurinji from Kenichi: The Mightiest Disciple inverts this trope. She wears glasses to tone down her appearance because she stood out too much and got ostracized for it at her last school.
In D.N.Angel there's a scene where Satoshi asks Risa for help in an investigation, and she thinks he's asking her out on a date. At first she's put off by him, but then starts to think he might be cute...if he takes off his glasses. She then asks him to take them off, and he does. (They're back on in later scenes, however.)
A one-time character in the Sailor Moon manga looks absolutely stunning when her glasses are knocked off - but since she can't see a thing without them, she immediately starts groping around the floor looking for them. Usagi then starts wondering if Umino's appearance would improve as dramatically if he took his glasses off. According toNaoko Takeuchi, it would.
In Heartcatch Precure, Erika ends up having Tsubomi get rid of her glasses in favor of contacts as part of her own makeover, though it doesn't initially stick - mostly because she can't stand someone so energetic. She ends up letting it stay, but she's spotted from time to time with her glasses on, but by the end of the series, she has them back on... and ends up having them off again in time for the third Pretty Cure All Stars movie.
Yutaka Hasebe in Servant × Service wears glasses when playing video games at home, but takes them off at work or when an acquaintance visits. Clearly it's out of this trope.
Subverted in Space Dandy, where when dealing with a girl with Nerd Glasses Dandy decides that she might just be "secret-hot". When he takes them off however, her eyes are still comically shut, prompting him to tell her to go slap her parents when she goes home.
Subverted (and confirmed) in, of all places, Archie Comics. In one comic, Veronica, always at the forefront of style, chooses to wear glasses with no lenses in order to look more fashionable. Ironically, everyone feels sorry for her because they absolutely know that glasses always make women look ugly.
Another story showed Betty wearing glasses for school while Veronica taunted her that she'd only attract "nerds and dweebs" (Betty didn't care one way or the other). When she saw Betty was actually attracting attention from handsome guys instead, she snatched Dilton's glasses in an attempt to show her up. The prescription was so high that she couldn't see, however, leading her to flirt with the principal.
Played straight in Watchmen. Laurie finds Dan much more attractive without his giant glasses. When they go into hiding at the end and forge new identities, he has apparently ditched the glasses in favor of contacts.
Superman couples this with The Glasses Come Off. Mild-mannered Clark Kent wears glasses, but he removes them to become the dashing Superman, with whom Lois Lane falls in love.
Peter Parker wore glasses in the earliest comics, but they were broken rather soon, after Flash Thompson pushed him. Fortunately, he never really needed them. (They had a weak prescription which his aunt insisted he use, as she was worried about him straining his eyes from reading so much. Other times it's Hand Waved as his spider powers having cured his vision.)
Batgirl (Barbara Gordon), in her earliest appearances, says that everyone sees her as a "Plain Jane," and though it isn't stated her glasses are clearly supposed to be a big part of this. This is even though, as drawn by Carmine Infantino in those comics, she pretty much looks like Gene Tierney with red hair.
There have been examples of this trope occurring for non-selfish reasons. For example, in Harry Potter And The Nightmares Of Futures Past, the future Harry is asked by his 11-year-old self why he isn't wearing glasses and he explains that Hermione fixed his eyesight with a charm because she got tired of his glasses falling off at inopportune moments.
The Princess Diaries (2001). The guy pulls them off her face and breaks them in his hand. That's right, not only is it shockingly, willfully unattractive to wear glasses on a day-to-day basis, you shouldn't even own them, little missy. Or remember you spent hundreds on that one pair.
To be fair, she did break his nice brush when he tried combing her hair...
Possibly hundreds of dollars worth of glasses that she would have to replace because you can't always wear contacts because he didn't think to start at the bottom of her hair and work up instead of trying to yank a brush through her hair. Yeah, totally fair.
Parodied in Not Another Teen Movie, where the protagonist is obviously beautiful, but all the guys are horrified by her glasses and ponytail, to the point that she's deemed more difficult to turn into a beauty queen than a pair of Siamese twins joined at the head and what appears to be a troll.
In the movie spoof Monster in the Closet, the hero is an overt Clark Kent parody: every time his glasses come off, the heroine literally goes into a slack-jawed trance at how handsome he "suddenly" is. And then the same thing happens with the monster, and it kidnaps him.
One of the first steps of the makeover in She's All That is glasses removal.
One of the older (though almost certainly not the oldest) examples comes with the Ruby Keeler character in the 1933 musical Footlight Parade.
Subverted and parodied in Scary Movie 2. When Theo tries to seduce the nerdy graduate assistant into giving her the keys out of the Haunted House, she takes off his glasses in hopes that it makes him prettier. All it does is make his eyes cross.
L.A. Confidential: A couple high-ranking characters tell up-and-coming police Sgt. Edmond Exley to "lose the glasses", since he wouldn't fit in as the only detective wearing them. He takes their advice as best as he can, going without them while sitting at his desk and while being photographed. This leads him to forget his glasses before a shoot-out. Oops!
In Strictly Ballroom, one of the first things Scott does after agreeing to dance with Fran is ask if she really needs her glasses, and then takes them off. The glasses are never seen again, and Fran's dancing (and love life) rapidly improves as soon as they're gone.
In the Spider-Man film, when Peter Parker gets his super powers, it corrects his eyesight. Mary Jane only starts to notice him after he stops wearing his glasses. In the sequel, Peter starts losing his powers and wearing his glasses again, but he sheds them once more when his self confidence (and powers) start returning.
Subverted in How to Marry a Millionaire (1953): A running gag is Marilyn Monroe's character quotes the Dorothy Parker line at the top of the page, takes her glasses off... and walks into things.
Subverted in The Pink Panther (2006): Inspector Clouseau puts the finishing touch on a plain woman's glamorous transformation by removing her glasses. She squints, stumbles, and smacks into a post.
Hilariously subverted in The Seven Year Itch where a man asks a woman who looks homely with glasses and her hair in a bun to take the glasses off and let down her hair. Guess what? Still homely.
In the Superman films, mild-mannered Clark Kent wears glasses to help look more "mild-mannered." He removes them when he's Superman and appears much more dashing. In the fourth film, a woman hitting on Clark tries to remove his glasses and suggests that he wear contacts, but he says that they irritate his eyes and keeps his glasses on to protect his identity.
In Waiting for Guffman, Corky has Eugene Levy's character take his glasses off to make him more presentable as a performer. It just makes his eyes cross comically.
Played completely straight with Adrian's granny glasses in Rocky.
Jokingly inverted in The Band Wagon, when Fred Astaire sees Cyd Charisse with glasses on and tells her he'd never noticed how beautiful she was before.
Played with in Monsters University with Randall who wore glasses, making him look rather nerdy. Mike suggested to remove them so he would look scarier and so the glasses won't hamper with his invisibility. Randall followed his advice and subsequently adopted his trademark squint.
In the "heroes don't wear glasses" sub-category: One of the main characters in the Young Wizards series of books, Nita, was originally described as wearing glasses in the first book. In the second book, the description went away. In the following books, one could probably forget she'd ever been described that way in the first place, and no explanation as to why she suddenly got 20/20 vision was given. It gets a passing explanation from Dairine, in Wizard's Holiday: Nita had astigmatism, but grew out of it, apparently.
In Vivian Vande Velde's book Now You See It..., the protagonist wears glasses and hates them with a passion, citing this trope on the second page. While the lesson of the book is essentially that looks aren't everything, she still manages to get rid of them permanently at the end of the book, making this a Broken Aesop. The story is meant as a bit of escapist fantasy for those who hated wearing glasses, since the author had the same problem and even dedicated the story to those share her distaste for bad eyewear.
Somewhat subverted in A Wrinkle in Time. Meg takes her glasses off and Calvin notices that her eyes are gorgeous. And then he tells her to put her glasses back on, because he wants her to keep her beauty a secret from unworthy admirers. Aww.
Buffy the Vampire Slayer: Spike needed them while alive, but tossed them afterward. His appearance gradually became more unkempt as he worked to build his reputation as a real killer - a street-fighting vampire.
In the SitcomGrounded For Life, the husband goes through ridiculous lengths to keep his wife from wearing her new glasses because he finds glasses so ugly that looking at them turns him off instantly. In a flashback, he even snubbed his would-be wife simply because she was wearing glasses.
Gob attempts to seduce his father's plain secretary to get some illegal business done. In an attempt to make this easier for himself, he asks her to take her glasses off and let her hair down, which makes her even less attractive, since without them, she has cross-eyes and crazy hair. He spends the rest of the scene trying to find an acceptable combination of glasses and hair.
Lucille demanding that Buster take off his glasses at a party. This resulted in Him accidentally hitting on her rival, Lucille Two.
Referenced in The Office when Pam wears glasses for an episode. Michael even tells her point-blank that to be attractive you have to take the glasses off. However it's soon subverted when Kevin is revealed to have a fetish for girls in glasses.
The reality makeover show 10 Years Younger employs Lasik eye surgery religiously.
In the first episode of Head Of The Class, when Arvid summons up the nerve to ask a girl to the school dance, one of the girls in the IHP class removed his glasses and his pocket protector to make him look better.
In the first episode of Sliders, Quinn needs reading glasses, yet this was dropped for later episodes.
Will Zimmerman of Sanctuary switches out his glasses for contacts in the Season 1 Finale.
In an episode of The Fresh Prince of Bel Air, Hilary makes her glasses-wearing boyfriend stop wearing them, saying he looks better without them. It becomes a plot point in the episode He gets in an accident with Will and sues for damages. When it's revealed he wasn't wearing glasses while driving as the law requires, the judge rules in Will's favor
On MTV's Made Sweet, nerdy girl Kitty wants to be in a high school beauty pageant. The makeover works better than expected for a few reasons. One, Kitty turned out to have a great body(long legs, small waist and big bust) that was hidden under the baggy clothes she always wore. Two, she had beautiful blue eyes that could be seen better without her thick glasses. She actually ends up winning second place!
On Seinfeld at the eyeglasses store, while George is buying new frames, Jerry looks at pictures of the female models on the wall, and says, "These women would be so much better looking without glasses."
Gender flipped in American Dreams. When Luke gets rid of his glasses, he gets the girl.
Josh Groban in several comedy appearances as himself wears thick glasses and makes a show out of removing them in order to cast a smoldering glance at the camera.
On Caroline In The City, Richard is always a prissy jerk with his glasses on and a plausible love interest with his glasses off.
In one The Big Bang Theory episode, Priya convinces Leonard to go without his glasses because he looks better without them. This is portrayed as a bad thing as Leonard spends the rest of the episode stumbling around unable to see with his new contacts and is part of a large swarm of changes Priya institutes to fix her boyfriend (culminating with having him remove Penny from his social group).
This trope is inverted in another episode, where Leonard is instantly taken aback when Penny puts on glasses.
A flashback in the second episode of The New Normal shows us Bryan and David's first meeting in a gay bar. Bryan is disinterested at first, until David inadvertently takes off his glasses, revealing his blue eyes.
Bryan: No wonder you keep those things sheathed. They're like Picasso's most overrated period. Or a box from Tiffany's.
Pretty much the whole point of the music video for the song "You Belong With Me" by Taylor Swift. She starts off with huge cokebottle glasses which she wears for most of the music videos, then right before she goes to the High School Dance, she takes off her glasses and puts on a pretty dress, prompting her true love to dump his skank ho of a girlfriendnote played by Swift in a wig and ending the music video with a True Love's Kiss.
In the late-80's, WCW had a storyline where Rick Steiner got involved with a fan named Robin Green, who regularly wore glasses and had her hair tucked under a baseball cap. When they went to go on their first date, she ditched the glasses and the cap and wore a VERY sexy outfit. Shortly afterwards, Robin dumped Rick and changed her name to the one she became better known by, Woman.
Doubly subverted in Wicked: When Galinda takes it upon herself to give Elphaba a makeover (in "Popular"), the first thing she does is remove Elphaba's glasses. The second thing she does is put them back on. All the same, Elphaba stops wearing glasses after that song.
Male example (kind of) in The History Boys: "Taking off my glasses is the last thing I do."
In Divine Wars and Original Generations, Princess Shine only has her ditch the glasses when she's in the Lolita look (since Latooni's her bodyguard). Even more, she gives her a new pair of glasses that doesn't obscure her eyes, showing her opening up more.
Also, Emma Emmerich. Raiden says she would look better without her glasses, but she tells him 'no', and not for the sake of practicality, either. She doesn't even need them; they're just frames. She says that she just likes glasses.
As part of Karen's makeover, Penny urges her to ditch her glasses for laser eye surgery.
Penny: Boys don't cut classes for girls who wear glasses. But boys find it way sick when those girls get LASIK.
In her own glam-up in a Something PositiveCross Over, Helen decides to keep them on. Not that many guys would be looking at her face, the way she made herself over...
When Kevyn has to lead the men for a while in Schlock Mercenary, the doctor insists that he drop the glasses - that in order for him to pull off the position of authority in this grave time, the men have to see his eyes. (This, despite the fact that earlier, while in temporary command, he'd so terrified the men that one of them called for his mommy - and that was while Kevyn wore his glasses.) The doctor is clearly aware of the difference between leading people and driving them before you in terror...
Also worth noting is that she tried contacts once, but her prescription is so ridiculously heavy they made her look like a bugged eyed anime character.
In the Whateley Universe, Bugs (Bunny Cormick) normally looks like the blonde bombshell of your wildest dreams. But her power is that she's a genius inventor, so, being Genre Savvy, she puts on the studious glasses to look like what one of her friends calls 'Professor Bunny'.
Subverted in Team StarKid's Me and My Dick, Joey takes down Sally's hair and attempts to remove her glasses only to have her go cross-eyed.
Parodied by The Nostalgia Chick back when she was wearing fake glasses. At the start of her Teen Witch review, she does the Beautiful All Along thing of taking off her glasses and shaking out her hair, but after that she puts the glasses back on, puts up her hair again and continues the review.
The animated series The Replacements features a supporting character named Shelton Klutzberry whose insanely thick and heavy glasses cripple his posture and pinch his nose, warping him into a stooped Jerry Lewis clone; if they are ever taken off, he instantly (and unwillingly) turns into a middle-school hunk. Of course, this particular example is so absurd in its extremes that it's likely a parody. His celebrity girlfriend immediately breaks up with him after finding all this out because she was attracted to his goofy awkwardness. In the same episode his sister Shelly has Todd take off her glasses. She is still very ugly.
In another male example, one of the episodes of Animaniacs with Minerva Mink had her falling in love with a nerdy-looking wolf who happened to turn into a hunky werewolf when the moon was out. Naturally, his glasses somehow magically disappeared and reappeared to suit whichever form he was in.
Gwen Stacy in The Spectacular Spiderman has a makeover in "Gangland," making her look less like Deb Whitman (a love interest from the comics, notable only for having glasses and being overdependent) and more like, well, Gwen Stacy. This included losing the glasses. While Harry and Peter did go through the standard awed gape, this is likely also because her hair was down and she was wearing a nice dress with a stole. She's kept the hair and the lack of glasses.
And of course, like in most incarnations, Peter had glasses before becoming Spider-Man but loses them afterward.
Parodied in Johnny Bravo. Johnny tries to teach a nerd how to be a chick magnet, but nothing works. That is until he removes the kid's glasses and gives him Cool Shades, which for some reason not only change him from nerd to a miniature Johnny, personality wise, but suddenly cause every woman to fall for him.
In Wakfu, Qilby the Traitor's glasses shatter when he merges with the Eliacube by transforming it into a prosthetic arm made of pure wakfu. Much like Aizen, this is part of The Reveal that he is the Big Bad.
In one episode of As Told by Ginger Macie greets her friends at a dance and asks how she looks, the first thing Dodie does is remove her glasses. Macie is barely able to see at the dance.
Anime and Manga
Ranma ½ subverts this trope. Mousse, a male member of the same tribe of "Chinese Amazons" that Ranma's self-proclaimed fiancée Shampoo belongs to, normally looks like a rather Bishōnen guy. Unfortunately for him, his eyesight is horrendous, and to counteract this he has to wear a set of Nerd Glasses that make him look absolutely ridiculous whenever he puts them on. Worse still, he has a bad habit of taking them off frequently, due to either vanity or wanting to be dramatic... and because he's Blind Without 'Em, he invariably ends up making himself look like an idiot. Even worse is the fact that his eyesight honestly isn't so hot with them on either; he's a bit better at seeing where his target actually is instead of walking right past it, but he still tends to confuse objects and people.
Ouran High School Host Club played it straight with Haruhi... But you'll notice that even while the twins are already making a run to the eye doctors's to get her contacts, nobody ever suggests that Kyouya ditch his Stoic Spectacles? Granted, there's a gender difference... But nobody involved knew there was one at the time.
And he's the Glasses Character, as Kirimi so rightly pointed out. Since they "cater to all types", that would mean they need a glasses character for those with a glasses fetish. Male glasses characters have smaller, frame-less or thin-framed glasses so they don't obscure their Bishounen faces. Haruhi's glasses don't do that while Kyouya's do.
In the Harry Potter series, Harry's iconic glasses are never said to make him any less attractive.
Averted a bit in A Wrinkle in Time and its sequels. Meg Murray hates her glasses with a passion, as well as her "mouse brown" hair and braces, and wishes she could look more like her mother. But her love interest/boyfriend/husband (depending on where you are in the series) Calvin O'Keefe, prefers her to wear them, saying "You just keep wearing those glasses. I don't think I want anyone else knowing what dream-boat eyes you have."
Newt in Good Omens is an average-looking guy in glasses. By all narrative standards, he should look better without them, except taking them off causes him to bump into things and fall over, which really doesn't improve his attractiveness. So he keeps them on.
Subverted in Glory in the Thunder. Barsamin's mother and Katarosi's grandmother tell them to take off their glasses for their first meeting, but they each think the other looks better with glasses anyway.
In The Fire Rose, when one of Jason's Salamanders comments that Rosalind is nice-looking despite her glasses, Jason immediately declares that glasses are just another accessory.
In the Harry Potter fanfiction "Deranged and Wrong", Harry replaces his iconic glasses at his 18th birthday for thinner square-rimmed ones and is immediately more attractive.
On the other hand, Wesley from Angel removes his glasses in his makeover as a Badass, in addition to growing a five-o'clock shadow. No mention is ever made of how he manages to see well. Fred also wears glasses only sometimes during the show.
Perhaps contacts. Or magic. But in the comic continuation of the series, Wesley is wearing his glasses again, so probably contacts.
Before his makeover, Wesley and Cordelia once spontaneously impersonate Buffy and Angel, in order to bring a new cast member quickly up to speed about their twisted relationship. Wesley intuitively recognizes that his keeping his glasses on in this role would look dorky, and quickly whips them off... and then fails to find a place where to store them, so he ends up looking just as dorky holding them in his hand during a passionate kiss.
Spoofed in Amy Acker's screen test, which involved Wesley falling in Love at First Sight with Fred due to a spell.
Wesley:(removing Fred's glasses) Now you truly are...perfection.
Fred: Whereas you are slightly fuzzy; can I have those back?
Bones: Booth finds Brennan quite sexy when she dons glasses in one episode.
Booth (seeing Brennan wearing someone's zany glasses): Right. What I want you to do is take off your glasses, shake out your hair and say "Mr. Booth, do you know what the penalty is for an overdue book?"
However, he stops wearing them during the episode where he's abusing the Goa'uld sarcophagus. Abuse stops, glasses come back.
"Evil Daniel" also didn't wear glasses in Absolute Power. The character also stopped wearing them when he ascended to a higher plane of existence. Both times.
Logan in Dark Angel also manages to keep his glasses for the entire run (shorter though it was) and when Max is lusting over him, she mentions how much they add to his appeal.
For the surprise of the watchers, when the time for the Obligatory Makeover in Yo soy Betty, la fea arrived the heroine ditched her horn-rimmed thick glasses for... fashionable, thin-framed glasses with a correct formula and compressed glasses. Her mentor Catalina Angel actually suggested her to try contacts, but because Betty had to go back ASAP to her former circumstances and she wouldn't have time to get accustomed to them, Ms. Angel just dragged her to the nearest optometrist and selected a better suited pair.
In one Peanuts strip, Peppermint Patty suggests that Marcie would look more sophisticated if she pushed her glasses up onto her forehead. After walking into a wall and a lamp-post, Marcie comments "Before I became sophisticated, I almost never had headaches."
In Time Hollow, you, as Ethan Kairos, have the option of enforcing this trope on Shrinking Violet Emily by using a Hole to steal her glasses. She does fine without them for a while, as flashbacks show her going about daily life and even baking cookies, but if Ethan never gives them back, she is shown getting horribly injured on her way to be fitted for contacts, and Ethan must then open a new Hole to give her glasses back and avoid this.
She has the kind of hair that's ideal for pinning up in a tight bun and then shaking down in slow motion halfway through the movie, and even has the thick, nerdy glasses to take off dramatically too. Unfortunately, this will never happen, because she needs the glasses to see.
Inverted in an episode of The Fairly OddParents, where King Arthur is a squinting, nearsighted pipsqueak — until he puts on glasses, and becomes a muscular, flowing-haired action hero with a deep voice.
Arthur: "I can see! I CAN FIGHT!"
In W.I.T.C.H., Taranee at one point gave herself a makeover to impress a guy she liked, which included losing her glasses - literally, in this case; the bullies stole them from her. Turns out he liked her the way she was, "glasses and all."
Not to mention the fact that her eyes literally set on fire when she's angry. Fire+contacts=bad idea.
In the comics, however, it seems she isn't one to adhere to this idea - when she found out that the Heart was fixing everything wrong with the girls, including Taranee's eyesight, it was the last straw and she initiated her own 10-Minute Retirement in anger.
And then parodied mercilessly when it cuts back to the shallow news anchor who spends the entire report being horrified by her appearance while she's trying to make a breaking news worthy report.
South Park mocked this trope, of course. Kyle tells a genuinely hideous girl that she'd look beautiful if she just put her hair down and took off her glasses. But when he takes them off for her, he discovers... nope, she's even uglier without 'em.
Played with in Holly Hobbie And Friends: Marvelous Makeover - "Cover Girl," in which K.T. the new girl is given a makeover, but the story is ultimately about accepting her for who she is.
In one episode of The Simpsons Milhouse tells Bart that his glasses make him look like a geek. Bart tells him that taking them off will make him more attractive. Because Milhouse is Blind Without Them this results in him getting injured and Bart feels guilty about it.
Hank and Peggy Hill from King of the Hill both wear geeky looking glasses that most people would see as uncool, especially considering both of their nerdy personalities. However in "Get Your Freak Off" when Hank and Peggy meet a very hip and trendy couple, they tell them their glasses look cool and call them "geek-chic".