Some of the dresses in 27 Dresses are considered this.
The costume department of 2011 movie Killing Bono clearly went to town in showcasing the absolute worst fashions of The Eighties.
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 titular 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!
My Big Fat Greek Wedding along with the wedding dressed that inspired the page quote, 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.
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."
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.
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, 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".
And in another instance, one wearing clothing so hideous even a Slaaneshi cultist would look down on.
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"
Live-Action TV
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."
Frasier 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!"
In another, she 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 that "and standing next to this, she'll light up like a bug zapper."
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-seeringly horrible he was dubbed "Tacky Shirt Man" during the opening Superheroes game, turning it into a Running Gag for the rest of the show. The shirts were chosen by the show's wardrobe department, not by him.
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.
Poor Buffy and Willow. Anya's bridesmaid's dresses got called this.
Spike: It's nice to watch you be happy. For them, even. I don't see it a lot. You glow. Buffy: That's because the dress is radioactive.
Benny Hill did a skit in which he was wearing a impossible tacky suit and he's strutting around,then they show a scarecrow wearing the same suit.
Also referenced in Short Trips and Side Steps, with the mind-manipulating Javaman stating flatly that there are only a handful of beings in the known universe to dress as tastelessly.
Paul Merton frequently wears these on Have I Got News for You (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...
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.
Stand-Up Comedy
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.
Webcomics
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.
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 a Doug Walker video, "Reverend Nutjob", he asked God to heal one guy's fashion sense (he was wearing a light yellow suit).
Western Animation
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 My Little Pony Friendship Is Magic 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!
The Green Lantern's outfit is this according to Duck Dodgers: "Yech! Black vinyl and latex. How cheesy can you get?"
