Doomed New Clothes

"Wow-ie, do I look sharp! Just in time for tonight's big dance but I'd better be careful not to get anything on my expensive new tux."

—Chuck, Chuck's New Tux

So you just bought some new clothes. It's a nice day, why not go for a walk? So there you are, ambling along, maybe even whistling.

This can't possibly end well. You will trip into a puddle, get caught by a splash of mud from a passing car, get soaked by a sudden downpour or the like. In extreme circumstances you will suddenly be passed by a hero chasing a villain and accidentally knocked into a pond or covered with rubble. Extra points if the dress is a Pimped-Out Dress.

And shoes? Well as Ben Elton once said, "Nothing opens a dog's bottom quite like the sight of a new pair of hand-stitched Guccis!"

Clothing Damage is a more extreme version, as is Naked Freak-Out (which is more titillating than either). See also Watch the Paint Job,Tempting Fate and Forced Into Their Sunday Best.

Interestingly enough happens quite often when Villains Out Shopping.

See also Watch the Paint Job, The Precious Precious Car and Priceless Ming Vase for other stuff doomed to be destroyed.

Examples of Doomed New Clothes include:

Anime and Manga

The Transformation Sequence in Moldiver causes the user's clothes to get shredded if they don't undress first. When we see the main character buy some expensive new clothes, its fate was inevitable.
Ranma ½: Akane is very proud and very happy. She has grown up a little bit, enough to make her buy a new bra. She never even got to wear it --Happosai steals it off the hamper at the bathhouse and tries to force female Ranma into it. Problem is, Ranma is significantly more grown up than Akane, and the bra is stretched out and ruined. Cue Akane's wrath.
In Hayate the Combat Butler, the titular character is at one point given a new cashmere coat to wear while out in town doing errands. Cue lampshade hanging en masse by everyone he meets. He does a spectacular job of dodging hazards, but then ends up jumping in a pond to save a friend of his master.

Oh no, I just spilled a can of paint! The kind that stains cashmere!

In Naruto, the titular character recently started sporting a Badass Longcoat to go along with his new level of badass. After the start of a decent showing, he promptly got his ass kicked, which climaxed in the destruction of the coat, among other things.
The fate of Asaka's Yukata in the anime Dokkoida?!.
In Pandora Hearts Oz gives his wibbly little servant Gilbert a nice new set of white clothes to wear at Oz's coming of age ceremony. Oz himself is wearing a splendid white outfit just for the occasion. During the ceremony, both Oz and Gilbert (mostly Gilbert) end up bloody (shows up nicely on white) before Oz takes a tumble into a very special hell.
The new outfit Lucy gets during the middle of any given Fairy Tail arc will almost inevitably end up more shredded than the one she'd been replacing due to damage.
Suzume: Chika gives Suzume some casual wear to use in place of the latter's uniform, but it gets badly damaged as a result of the events in Tokyo, forcing a reversion to the uniform.

Comics

In an 80's issue of X-Men, Rogue spent the better part of the morning looking for missing teammates Nightcrawler and Rachel, after the team's fight with Nimrod, to no avail. Once the stores opened, she treated herself a new outfit. Um, then the Mutant Massacre happened.
- Happened to her again in the Fantastic 4 Vs The X-Men story arch. She bought a new outfit in Latveria while staying at Dr. Doom's castle (long story). When she returned, a fight broke out and she absorbed the Human Torch's powers. Her outfit was not made of unstable molecules, so....
Francine from Strangers in Paradise and there's nothing she can do but change into some trampy clothes a friend dug up. Fortunately it turns out real happy for her. Well, for a while.
An early '60s Archie comic had Veronica wearing a fashionable Chinese silk dress. She gets increasingly angry when everybody (Betty included) thinks the slit skirt is a rip. Then, when Big Moose, of all people, knows what it is and compliments her on it, she's so gobsmacked that she doesn't look where she's walking, and falls down a long gravel embankment.

Film

Judy Garland in In The Good Old Summertime. It's not bad enough that she's carrying a parasol on a windy day, she has to get knocked over by a guy as part of a Meet Cute as well. Note that this can cross over with the old umbrella-getting-turned-inside-out gag (which should have its own trope) for added pathos.
Susan in the Hayley Mills version of The Parent Trap. There she is, having a nice conversation with a boy on a porch, and her new dress gets cut up as part of a feud with her lookalike and as-yet unknown sister Sharon.
Crossover with Fur and Loathing in the film It Could Happen to You. The bitchy wife, who just became a Rich Bitch, buys a fur coat, and as soon as she gets out of the store, her coat gets hit with red paint.
In Dogma the angel Metatron seems to complain about his clothes getting ruined. When it happens one time, he reaches over and uses God's dress to wipe something off his clothes. She's not too happy about that. (Yes, it's a comedy).
Not quite new clothes, but still: Thorndyke wears a freshly-pressed driving uniform in The Love Bug. Too bad the Irish Coffee-inebriated Herbie projectile coughs whipped cream all over him.
- Well, Thorndyke was the one who put Irish Coffee into Herbie's system, so this was Herbie's (unintentional) way of getting back at him.
Marty is given a "Western" outfit and a new pair of cowboy boots by Doc in Back to The Future III. A bear eats the boots. Similarly, his ancestor gives him a new hat, only to have it lost and probably trampled by Buford "Mad Dog" Tannen's horse. The outfit gets torn up as Buford drags Marty down the street.
Lina Lamont wears a new dress (hey, she's a famous actress at a movie premiere, of course it's a new dress) to a party celebrating her newest movie in Singin in The Rain. She ends up covered in the cake that's been specially made to honor her.
- Also from Singin' in the Rain, Don Lockwood ends up having his new suit literally torn to shreds by fangirls. This is immediately followed by a Meet Cute, following the pattern noted above.
In The Incredible Hulk movie we see Banner buy new clothes and know that those clothes are gonna be toast. Although the pants survive.
Raising Arizona's main character buys some new shoes then chases after his perverted boss and ruins them.
Oh, Ofelia. "Here's your new dress, shoes, and hair ribbon. Be sure to keep them clean, you must look good for your father's party tonight." To give the girl credit, she tries to take some care of her clothes by taking her fancy dress off and hanging it on a branch before she goes hunting for a magic toad under a long-dead fig tree. However, it doesn't work, the dress gets lost, and by the time she finds her dress and wanders home again, the poor thing is covered head-to-toe in mud.
Fantastic Four: Rise of the Silver Surfer. Johnny is frustrated that he must destroy his new suit to chase the Silver Surfer. One wonders why Reed didn't make an unstable molecule tuxedo.
- Probably because Reed Richards Is Useless.
Raiders of the Lost Ark: Marion's dress from Belloq gets dirtied from being in the Well of Souls, and Indy tears up most of the skirt.
Played with in Blazing Saddles, when bandits overrun the town of Rock Ridge early in the film. A well-dressed dude is lassoed and dragged behind a horse through the mud. He turns to the camera and simply notes: "Well, that's the end of this suit!"

Literature

Due to Fashion being Serious Business to fire demons in Lonely Werewolf Girl, when Malveria wears one of her new outfits to a human club before having to go to a fire demon week-long ball, she is rather upset that the club turns out to be the setting of a pitched battle between werewolves cliques. Thankfully she manages to convince the other Fire Demons that the blood stained wreck is "battle chic".
In the second Dragonriders of Pern novel, F'lar and Lessa are wearing new outfits to a wedding. F'lar ends up in a duel with T'ron, during which he gets his suit cut up, and Lessa has to rip up her dress to make bandages.

Live Action TV

Lizzie McGuire had this happen on the day she was trying for Best Dressed in the yearbook. Of course, buying new clothes she couldn't really afford and planning to return them for a refund later was just asking for it.
- That's So Raven had an episode with a similar plot, but she was wearing the dress for a party.
The opening credits of Sex and the City feature Carrie walking down the street in a nice dress, only to be splashed by muddy water from a passing bus.
An episode of Angel had the gang buy new clothes to go out to the ballet. When Fred points out that they're broke, Cordelia assures her that they can tuck in the tags and return the clothes tomorrow. Of course, that was before they had to do battle with a group of demons.
Happened to three of Larry's new, identical shirts in one episode of Curb Your Enthusiasm (from his own blood, makeup, and tearing the last one in half as he and a friend raced to claim it, in that order).
In an early episode of Degrassi, Emma has been feeling moody lately so her mother takes her out to buy some new clothes to cheer her up. The very next day we realize why Emma's been so moody when her first period coats her new skirt in blood.
In Eureka, Alison is in the middle of trying on her wedding dress when she gets called to deal with an emergency. She doesn't realize until she gets there that the emergency is a mud volcano.
In A Very Peculiar Practice the suit Bob gets as a bribe for skewing a drug trial needs cleaned, again and again.
In Casualty Zoe wear a brand new, £300 pair of shoes to work one morning, on the same day that Holby City Emergency Department is inundated with norovirus sufferers. And it's her turn to be in charge of the isolation area for those vomiting patients. Her shoes make it all the way through the day unharmed, thanks to the use of surgical booties to protect them... and then, on her way to her car at the end of the day, she's walking past a massive puddle just as an ambulance drives in at high speed.

Newspaper Comics

Toyed with in a Calvin and Hobbes strip: we see Calvin checking out a mud pit, adding water to get just the right consistency... next thing we see is Calvin at Susie's house, inviting her to "Put on some nice clothes and let's go for a stroll!"

Video Games

In episode 4 of the Back to The Future games, Emmett is seen wearing a suit that belonged to his girlfriend's grandfather. Not only does the suit get destroyed, but Marty has to engineer its destruction personally.

Web Original

Chuck's New Tux by Harry Partridge which involves Chuck wearing his new (white) tuxedo for the big school dance and dodging various messes along the way, eg. a woman carrying lots of drinks. Eventually he ends up being sent flying towards a giant wedding cake but he misses and gets stabbed by the pointed fence just beyond the fence.

Western Animation

Scrappy (the kid, not the dog) struggles to protect his Sunday Clothes (1931) in a theatrical short. He successfully dodges a gang of bullies and rides over a mudhole on a sewer worker's head, but in the end... well...
The future Anita Radcliff in the animated version of One Hundred and One Dalmatians. Clearly she spent hours ironing her new spring suit, but there she goes into the pond! Note that when you combine Meet Cutes and new clothes the probability of catastrophe increase exponentially.
Veronica Vreeland in Batman: The Animated Series. There she is, buying a new dress for her date with Bruce Wayne and along comes a spooked Harley Quinn. Her car gets ruined, too.
- Well, considering that Veronica actually got taken hostage by Harley, I don't think she was too concerned about the car at first.
In an episode of Teenage Mutant Ninja Turtles: Fast Forward, Raphael tears his own (rented) tux to shreds as he draws his laser-sais when a fight broke out.
My Life as a Teenage Robot "Call Hating", Tuck walks home with a fresh haircut and a white tuxedo. Robots attack the city. Mud was involved.
- A mix of this and Watch the Paint Job for Jenny as well, who got a new outfit/paint job for Don Prima's party, only for the Crist Cousins higher a guy who specializes in mud to attack her for the sole purpose of ruining it.
SpongeBob SquarePants falls victim to this trope several times in the episode "Picture Day", in which he attempts to stay clean while avoiding (among other things) being mistaken for a trash receptacle and being dumped into Patrick's peanut butter and jelly taco...
One episode of Wow! Wow! Wubbzy! revolves around Wubbzy trying to get to the photographer without getting all muddy, but Failure Is the Only Option, it seems.
In the Disney version of Cinderella, the title character shows off her new pink dress made by her mice friends. Her stepsisters aggressively tear it to pieces.
Lampshaded on The Simpsons

Principal Skinner: Normally I wouldn't go near a giant chocolate cake in my dress polyester, but with Bart Simpson safely encapsulated, I'd be delighted to pose.

An episode of Jimmy Two-Shoes had Lucius show off his new Nice Hat. Jimmy was around. You can guess the rest.
One of the running gags of My Little Pony:Friendship Is Magic, is that Rarity, the fashionista of the group, often has her nice clothes get messy, dirty, or destroyed.
- Special mention goes to Swarm of the Century, where the parasprites, after turning Extreme Omnivore, eat the very clothes Twilight had complimented Rarity on making the previous day.
- She successfully Defied Trope this during the brunch in "A Bird in the Hoof".

"Nobody move, and my dress won't get hurt!"

Real Life

Many a schoolboy knows that the very first day he wears a brand new pair of shoes to school, his enemies (or even his friends), will say "Oooh, are those new shoes?" and then proceed to tread on his toes repeatedly, thereby completely destroying the toe-caps. On the upside, it probably does make the shoes a little more comfy to walk in...