An advert for UK men's clothing store Jacamo, in which the Style Police went after badly dressed men, suggested that guys who didn't shop at Jacamo wore outfits of carefully crafted hideousness, rather than just pulling on a T-shirt and a pair of jeans.
Anime and Manga
Kuniya's gimmick in Sayonara, Zetsubou-Sensei is his absolutely atrocious fashion sense, which he demonstrates whenever he's out of his school uniform. It's bad enough that when the class is watching a field news report on a crime, they spot him in the background with an incredibly gaudy t-shirt and get so distracted that nobody can even remember what the crime that was being reported was (and one of them even asks if it was a guy wearing a gaudy t-shirt and staring at the camera.)
Garfield's owner, Jon, frequently dresses in gaudy outfits for dates.
In the Astérix album Obelix and Co., the familiar-looking Roman economist Preposterus, who is trying to introduce free-market capitalism to the village (hoping to cause their decadence with money), buys lots of Obelix's stock at inflated prices and tells him that he should now put some of the money back in the economy by spending it on expensive clothes more appropriate for a businessman. Obelix is so rich that he buys an entire peddler's stock of fabrics and then pays a lot of money to the village seamstress to make his dream outfit from them. This turns out to be strange-looking purple and blue breeches and a huge yellow bow. Obelix is convinced he is a Sharp-Dressed Man, but everyone else hates it, with only Asterix retaining the good humour to laugh at him instead of just shooting him waves of contempt. Then he gets everyone else into the menhir craze, and they all start dressing like that, too.
Luke Cage used to wear a open-chest yellow silk shirt with a high collar. In The Pulse, Janet Van Dyne is trying to design Luke's new outfit, and most of them make his old outfit look like an Armani suit.
Black Canary's 80s costume has received much lampooning since she got rid of it, including one issue of Birds of Prey where she sees action figures of herself in it and immediately buys all of them so no one will know how ugly it was. Not to mention the one cover that showed her gleefully burning the thing◊ when she returned to her classic look.
Navarone gets a set of tacky armour in Diaries of a Madman, as a way of Celestia getting revenge on him for spoiling one of her plans.
True Stories is the absolute Trope Codifier. A fashion show of nothing but. It starts with suits made of things like grass turf or red brick stucco, and moves on to increasingly hideous outfits. Topped off with bridal gowns with headpieces about a dozen feet tell. Has to be seen to be believed.
Most of the bridesmaid dresses in Twenty Seven Dresses are considered to be tacky. The male lead thinks all the brides made Jane wear such ugly outfits on purpose because they couldn't stand having a gorgeous, tall and elegant woman like her next to them.
The costume department of 2011 movie Killing Bono clearly went to town in showcasing the absolute worst fashions of The Eighties.
In My Cousin Vinny, the title character is held in contempt for not wearing a suit in court. When his only suit is accidentally thrown into a mud puddle, and the dry-cleaners is closed, he needs a replacement to keep himself from another night in jail. Cue the only suit for sale in the entire town: A three-piece getup in maroon.
In 101 Dalmatians, particularly the live-action adaptation and its sequel starring Glenn Close, Cruella's outfits are monstrously over-the-top and shock anyone who sees them - but nobody is brave enough to confront her about it. Cruella is in search of the "perfect" fur coat, and is convinced that it must be made from the skins of the dalmatian puppies.
Stanley Ipkiss' pajamas in The Mask - one even inspires Lt. Kellaway to use Bat Deduction to conclude he is the title character.
Stanley: This is... impossible! Kellaway: Those pajamas are impossible. This actually happened!
The ABBA outfits in Muriel's Wedding (which clearly inspired the film Mama Mia!) are just truly horrible.
My Big Fat Greek Wedding: Along with the wedding dressed that inspired the page quote, there are has hideous bridesmaids dresses that her cousin Nikki picked out. While the rest of her family coos in awe, Toula's response is a horrified gasp.
In Django Unchained, Django's first choice of clothes as a free man◊ are a royal-blue coat with matching knee-breeches (tied off with blue ribbons), buckled shoes, and a very large, lacy bow tie. When one of the slaves he's talking to realizes that he picked the outfit for himself (rather than being forced to wear it as she's assumed) she's astonished.
Cheery Littlebottom embraces that she is a female, against Dwarven traditions of looking gender neutral. In The Fifth Elephant she and other dwarves like her make some dresses to show off their newfound femininity, but their dresses look silly. Others are too polite to point it out. The dresses are described as going all-in on gaudy girliness, because when you're breaking out of a thousand years of tradition, subtlety doesn't come into it. At the end of one novel, Cheery admits that that one green dress does make her look like a big cabbage.
Happens in the Discworld novel Pyramids. Ambassadors to the Djelibeybi court have tried to look their best, but because many items of clothing from Djelibeybi's seven thousand year history are sometimes employed only in very specific circumstances, they end up looking like utter fools. The effect is described thusly:
"If a foreign ambassador to the Court of St James wore (out of a genuine desire to flatter) a bowler hat, a claymore, a Civil War breastplate, Saxon trousers and a Jacobean haircut, he'd create pretty much the same impression."
The Discworld Diary for Unseen University describes UU scarves and other apparel in the school colors as being an eye-watering mix of colors, allegedly intended to approximate octarine for non-wizards' eyes.
In To Say Nothing of the Dog by Connie Willis, all of Tossie's over-designed dresses tend towards this, at least in the eyes of the time-traveling protagonists, who are pretty put off by most Victorian design. But especially Tossie's dresses. Girl loves ruffles.
Near the end of Barrayar, Miss Droushnakovi had in mind a lacy wedding dress, but - fortunately, as it turned out - Lady Alys Vorpatril took an interest in her case and averted this trope.
"No, no, no!" she cried, recoiling. "All that lace—you would look as furry as a big white bear. Silk, dear, long falls of silk is what you need—"
Taura's civilian wardrobe also tended to this, which was why Miles had her consult his Aunt Alys when she arrived for his wedding. Alys' first stop in giving the bioengineered supersoldier a makeover was to have her previous wardrobe burned.
Rita Skeeter is also described as dressing in ridiculously tacky fashions such as magenta robes with maroon furs at the collar and sleeves.
In the Louisa May Alcott novel Eight Cousins, the Naïve Everygirl Rose showcases a very "fashionable" outfit. As it's a book, much is left to the imagination, but the narrator and characters comment on how overdone and awful it looks on her, except for the slave-to-fashion aunt who put her in it in the first place. Rose's uncle even lambasts the aunt on how unhealthy it is (then again, whalebone corsets? he has a point.) This is a case of Writer on Board, as Alcott has Rose showcase a much more modest and simple outfit to emphasize the simple, modest young lady she is (and that all her readers should strive to be).
Early in Duty Calls, Ciaphas Cain is attacked by followers of Slaanesh, one of whom wears a jacket so hideous that Cain claims wearing it is a capital offense. He refers to the man thereafter as "Vile Jacket". He also mentions that local fashion is so hideous that even a Slaaneshi cultist would look down on it.
In the Wild Cards series, Dr. Tachyon is frequently described as dressing like this whenever he has the opportunity to dress himself. Canary yellow, emerald green, royal purple, cardinal red, and sky blue can all make an appearance in the same outfit. Apparently, this is considered a normal Takisian wardrobe, but since he's living on Earth, almost every human who looks at him comments on how ridiculous he looks. It's compounded by his metallic-red hair.
In Alexandre Dumas's novel the Forty Five Guardsmen we are informed that they have no uniform and, since they are just arrived to Paris, they are provided with money to buy new clothes, the results were a motley assortment of styles and decorations, "generally in bad taste".
In the Shadow Grail series by Mercedes Lackey, the main character has to attend the school's New Year dinner and formal dance, but doesn't have any formal wear. She goes to the storage room of dresses that Oakhurst Academy has to find something suitable. Unfortunately, as a friend puts it, it's where 'bridesmaid dresses go to die'. Fortunately, said friend is a good seamstress and is able to make a nice formal dress out of two terrible ones from the 'Little Closet of Horrors". The boys apparently have their own version of said closet, with secondhand rent-a-tuxes.
In the Acorna Series, Acorna finds the traditional costumes of her people to be far too ostentatious, modifying them to be more discrete. Her kinsfolk react by thinking she is still in her underwear.
The Bartimaeus Trilogy: Nathaniel's fashionable, very tight trousers in The Golem's Eye are mocked by Bartimaeus and Kitty.
In Wheelof Time, the Tinkers, wandering Actual Pacifist expies of the Romani, tend to wear rather blandly-designed clothes compared to some of the other cultures that Robert Jordan indulged his Costume Porn tendencies with, except that the color choices are best described as eye-searing.
The combinations could be described as having been picked by someone who was completely colorblind, but they're so hideously clashing, and uniformly so, that you can't get there by mere chance.
Mimi on The Drew Carey Show regularly dressed in outlandish clothes and overdone makeup, which of course got a number of jokes from Drew and his friends (although Mimi would have her own jokes to snap back with).
Friends did an episode that touched on these bridesmaid dresses. Rachel said she looked like something you drink when you're nauseous, and Chandler called her "Princess Bubble Yum".
In How I Met Your Mother season 1, Lily tried on some bridal dresses in her price range which were truly groan-worthy.
It had one episode when Roz mentioned she hated those kinds of bridesmaid dresses. Subverted when Frasier takes control of the wedding and chooses tasteful dresses for the bridesmaids, at which point Roz agrees to be Daphne's bridesmaid. Double Subverted when, after Roz has agreed, she convinces Daphne to take control of her own wedding, and Daphne says the first thing she'll change is the bridesmaid dresses: "They don't even have poofy sleeves!"
Roz once shows Frasier the dress she was supposed to wear for a wedding back in Wisconsin. After the typical cringing, Roz mentions that they're supposed to be awful "so the bride will glow". She then adds: "And standing next to this, she'll light up like a bug zapper."
Another hideous green taffeta creation elicits a comment from Frazier that if she gives it to Goodwill shell "make some Irish drag queen very happy."
The Puffy Shirt in Seinfeld. "I don't wanna be a pirate!"
Colin Mochrie is especially remembered for his insanely tacky shirts. During one episode, his shirt was so eye-searingly horrible he was dubbed "Tacky Shirt Man" during the opening Superheroes game, turning it into a Running Gag for the rest of the show. In actuality the shirts were chosen by the show's wardrobe department, not by him, since he was usually the one in front of the green screen during "Newsflash" games, so his shirts were chosen so they didn't interfere with the Chroma Key.
Ryan Stiles' custom-made shoes were also frequent targets, including a pair in leopard print, a pair in bright blue, and an impressive black-and-white pair with flames on the sides.
Step out in style with the 6th Doctor's patchwork coat, cat pin and iconic question mark lapels! Enjoy fashionably tasteful time travel with this fantastic Forbidden Planet Exclusive T-Shirt designed to commemorate Colin Baker's iconic outfit!
Paul Merton frequently wears tacky clothes. The rest of the time he wears a Fun T-Shirt. Once lampshaded when Paul wore a bright pink shirt with a yellow-gold dragon design on one shoulder.
Ian:I say, Paul, I think someone's thrown up on your shoulder. Paul turns to the plain shoulder and brushes away an imaginary piece of lint. Paul: Thanks Ian, I wouldn't have noticed otherwise!
Angus Deayton went in for this back when he hosted the show too. Most notorious was his bright brown suit.
Have I Got News For You: The Shameless Cash-In Book includes a look at the regulars' wardrobes. Angus's contains "Silk suits, many of them tragically brown" and Paul's contains "Shirts of such unyielding hideousness as to take your breath away". Ian, meanwhile, goes for "Nondescript woollen jackets and cheap loud ties (non-matching)".
In Entourage, Vince almost dismisses Aquaman because of the first costume design.
In a "Non-Denominational Holiday" episode of X-Play, Adam dissed the antlers he wore, while Morgan dissed his sweater.
The Chase's Bradley gets a ton of mileage on Paul Sinha's straight from the 70s white suit. So does Paul. Behold◊. There's a reason his twitter feed lists him as a: "Prisoner of ITV's Fashion Consultants".
Ally McBeal: Ally once went to her client's wedding as her bridesmaid. The dress were terribly fluffy and of some vivid colour. Nelle and Ling observed that it looked horrible. When Ally was wandering in the streets still wearing said dress, one couple liked it (or was amused) and they wanted to take a photo of her.
Top Gear: James May often gets made fun of for his fashion sense, especially his loud and/or flowery shirts. He has pointed out in several interviews that he actually spends quite a bit of money on clothes, but "manages to make them all look like crap."
In The Comedians of Comedy, Patton Oswalt talks about how he hates stand-up comics who start their bits by making fun of the clothes they're wearing. Not only does it require them to wear stupid clothes to every single gig, but it doesn't make any sense. Did someone forcibly dress them moments before they got onstage?
Robin Williams talked about these when discussing golf in his "Live on Broadway" special:
Brayko's clothing in Alpha Protocol. Thorton will repeatedly mock him about this depending on your conversation choices. This gets Brayko to like you.
Benny's checkered suit in Fallout: New Vegas. Once the Courier kills him, several NPCs will comment on how tacky the suit was.
NPC: I know Benny was murdered, but if you ask me, the real crime was that checkered suit.
Anything Evelyn is proud of making in Rune Factory 3, though she does also sell you different colored versions of your regular outfit. You never get to see any of the crazier things she's made, but the more normal ones (as in, the ones not made of fish scales or cheese fondue) are still not only horrifying but meant for quite possibly the worse people imaginable.
Inverted in this comic of Our Little Adventure. When Julie goes to her appointment with the Everwood council, she passes a small group of nobility. Each of those nobles has an outfit more ridiculous than the last, though Julie thinks they're "stately and beautiful."
"You put on a few of your more ostentatious devices. Luckily (or unfortunately) you grew up alone, so there was never anyone around to point out how ridiculous you look."
the Prince of Heart outfit◊, involving dark pink bloomers and white tights. Dirk is understandably relieved to hear that he isn't actually required to wear the clothes constantly while god tier.
God Tier designs in general are pretty hit and miss, which is the point. The Bard of Rage clothes on their own are pretty tacky, but then you see that their most distinguising feature is an enormous codpiece. And Meenah actually complains about the Thief of Life clothes are refuses to wear them whenever possible.
Jericho of the Whateley Universe wears clothes so horrifically glaring and mismatched that people tend not to notice that he's hanging with one mutant who's mostly velociraptor and one mutant who's mostly anaconda.
In the Doug Walker video "Reverend Nutjob", he encountered a man wearing a light yellow suit and declared "Lord, heal this man's fashion sense!"
After a picture of Wil Wheaton wearing a clown face sweater became an Internet meme, he started using the image as his photo in his columns and on his site.
One of the outfits Kim Possible tries after her regular mission duds are ruined is a mecha-style suit built by the Tweebs. The sight of it reduces Drakken and Shego to fits of hysterical laughter.
The episode "Suited for Success" had Rarity, the local fashion designer, make dresses for her friends. Her first dresses were fine but her friends couldn't see it, and gave her strict directions for a second go. She finishes up the garish designs just in time for a fashion show for a world-famous designer.
Hoity Toity: Who is responsible for subjecting our eyes to such horrors?! Not to mention, wasting my valuable time!
In "Sonic Rainboom", Rarity's new magically-generated butterfly wings go to her head, and she performs in the Best Young Flier's Competition wearing Uncanny Valley Make Up and a ridiculously showy outfit that looks like something a Carnival dancer would wear.