Well, as far as she's concerned? Lots.
This character will see them as a tremendous pain in the ass. It's easy to stumble, the heel snaps like a twig, they make your back, legs, and feet sore, and good luck dancing or walking for long periods of time in them.
This trope is when high heels are treated as cumbersome or unpleasant and more trouble than they're worth. This can be either through the characters openly complaining about wearing heels or by showing characters being obviously encumbered by them. It is often Played for Laughs.
Any show about men dressing up in drag for the first time is guaranteed to bring this up in a not-so-subtle message about walking a mile in a woman's shoes. This trope can also show up as part of a tomboy's Femininity Failure. Subtrope of Fashion Hurts and Agony of the Feet, and sister trope to Of Corset Hurts. Varying Truth in Television.
- Kate Spade New York has produced a series of online-video ads called Miss Adventures. In the episode "The Joy Ride," Anna Kendrick and Zosia Mamet meet for the first time when Zosia lets Anna share a cab with her. But when politeness delays their destination decision, the driver (Joshua Safdie) leaves to use the bathroom. Over Kate Spade accessories, they bond during the endless wait for him to get back.
Zosia: This is like Waiting for Godot.
Anna: In heels. Ow!
- In Princess Jellyfish, none of the Amars women are capable of walking around in the high heels Kuranosuke gives them as part of their makeovers. Mayaya freaks out when she learns that he's also taking them out to a fancy restaurant, but twists her ankle and falls when she tries to run away, blaming it on the shoes.
- Excalibur: When Meggan and Phoenix have a "Freaky Friday" Flip, the usually-barefoot Meggan immediately complains about how Rachel's Combat Stilettos hurt.
- Wonder Woman (2006): Diana complains to Black Canary about the platform heels Canary included in her disguise after spending the night fighting in an underground illegal fighting ring. She wasn't excited about the shoes when she first saw them and declared that wearing them was messing with her back.
- The Victors Project: Cora mourns having to wear five-inch, or even eight-inch, Capitol heels.
- In Frozen II, after a long day out, Anna takes her heels off and walks barefoot. The movie doesn't overtly emphasize this, and she doesn't complain about them, just casually takes them off as she nears home, hugging them to her chest as she smiles fondly at her family.
- In 40 Carats, Mrs. Margolin pressures Ann to wear high heels more often, even though they hurt her feet. When most of the main characters go out dancing together, Ann's heels cause her to quickly become exhausted, while her mother Maud, who is wearing comfortable shoes, continues dancing energetically.
- The film adaptations of Carrie:
- The 1976 version has a lighthearted example. During the prom, Miss Collins tells Carrie the story of her own embarrassing prom, where she wore three-inch spike heels so that her kiss with her basketball player boyfriend wouldn't be so awkward. This became a problem when his truck broke down on the way to the prom. She had to walk half a mile in those heels to get to the dance, by which point she was too tired, and her feet too covered in blisters, for her to do anything except sit and talk with her boyfriend.
- A very dark example happens in the 2013 version. The mean twins Nicki and Lizzy are singled out during Carrie's rampage, where she telekinetically holds them down onto the gym floor to be Trampled Underfoot by the horde of people trying to escape. This is a high school prom, with lots of girls wearing high heels — and you see visible stab wounds from the heels on the twins' backs. Elsewhere in the same sequence, some girls are seen tripping up in the rampage, presumably thanks to the heels they wore that night.
- Downplayed in Cloverfield. Lily gets stuck in heels due to the monster arriving in the middle of a surprise party. Although she doesn't complain, as the film goes on and she has to do things like walk several blocks and run through a subway tunnel in them, she begins to limp visibly, and finally gives up and just takes her shoes off.
- In & Out: After the aborted wedding, one of Howard's relatives rests her feet on a chair and rubs them after taking off her high-heeled shoes.
- Infamously averted in Jurassic World, where Claire manages to hike through brush and outrun a T. rex in high heels without ever complaining about them or having attention drawn to them. In fact, this was done on her actress' own insistence, since the original plan was for her to run through the jungle barefoot.
- In Mrs. Doubtfire, Daniel complains about the high heels he's wearing while walking home from his first day as Mrs Doubtfire.
Mrs Doubtfire: If I find the misogynistic bastard that invented heels, I'll kill him.
- Romancing the Stone: Joan is trying to hike through the jungle in high heels and keeps falling. Jack grabs them and chops the heels off using a machete. She says "Those were Italian". He says "Well, now they're practical".
- In She's the Man, Viola tells her mom, over the phone, that she is definitely not wearing high heels at her debutant event because they are "a devious plot to make a woman's butt look smaller. And make it harder to get away". Incidentally, she does this while walking past the principal, who overhears and then tells a second bystander that it is indeed very hard to run in high heels.
- In Some Like It Hot Jack Lemmon and Tony Curtis have to disguise as members of an all-female band; Jack Lemmon, dressed as a woman and running to catch a train, plaintively asks how women can walk in high heels.
- The Wedding Year: When Violet runs out of her wedding, Mara chases after her and yells for Violet not to make her run in high-heels. A little bit later Mara has to take her shoes off, and walks with a limp for the rest of the scene.
- In xXx Xander Cage is drugged by government agents and wakes up in a diner that is about to be robbed. He quickly realizes that the scenario is a test because too many things about the diner did not add up. The clincher was that the waitress was wearing high heels. No waitress would wear high heels to work since she would be crippled in a few days.
- In Bombshells, a short story within The Dresden Files, Molly Carpenter suffers through wearing a pair of very high heels to infiltrate a fancy party. Andi the werewolf, wearing a similar costume with similar shoes, hints that she's in pain too - but says it's just a matter of getting used to it. Molly doesn't seem convinced.
- In Cheaper by the Dozen, Mother Gilbreth protests her daughters' decision to wear high heels in high school using the family obsession with efficiency. She tells her oldest, Anne, that it's absurd for her and her sisters to go around in obviously tiring shoes while their father lectures around the United States on removing wasted effort.
- The Estuary: Hillary mentally bemoans having to walk in the high-heeled Thigh-High Boots she uses to attract johns.
- In Harry Potter and the Deathly Hallows, Hermione comments on her high heels hurting her feet at the wedding. She then has to make her escape in them, but that goes without comment.
- Hardy Boys: In "Trouble in Warp Space", actress Jerri Bell asks the director if there's a way to re-write a scene so that she doesn't have to run down a hill in heels.
- During the first book of the Journey to Chaos series, Princess Kasile compliments Tiza's shoes as being practical and suited for the professional mercenary: easy to walk in and great for kicking people. She compares these shoes to the "high-heeled monstrosities" that she has to wear, being a princess and all. This was said to pacify Tiza and for "practice" in pacifying hostile people, so how much she truly believes this is not made clear in the scene.
- Secret Santa (2007): Shawna notes that while high-heeled boots "made her legs look great," they "weren't made for walking for hours."
- In an episode of The Big Bang Theory (The Wildebeest Implementation), Amy buys high heels, but feels sore when walking in them.
- Inverted in an episode of Cybill, where Cybill takes her friend Marianne camping. Marianne has only ever worn heels, and so has trouble keeping her balance in flats.
- Doctor Who has many examples. One of the more notable ones in Classic Who is Romana I, who discovered that the warnings from the Doctor to wear sensible shoes were not unfounded. She ends up taking off her heels and continuing barefoot.
- Dollhouse features an example in which Echo (as Roma Klar) mentions that her feet hurt badly after a day in stilettos. Considering how experienced she is at wearing them by this point, it's significant that she's never become accustomed to the pain.
- The Falcon and the Winter Soldier features Sam Wilson dressing up as a proper Fashion-Victim Villain nicknamed "Smiling Tiger" when he, Bucky and Zemo infiltrate Madripoor. As the ensuing shootout and foot-chase reveals....it's really, really, really hard for a seasoned soldier to run in heels.
- Friends episode The One With Monica's Boots focuses on, well, a pair of high-heeled knee boots owned by Monica. Even putting them on causes her to yell in pain; standing and walking is obviously torture. This leads to all kinds of problems.
- Gilligan's Island: In "Gilligan the Goddess'', Gilligan is Disguised in Drag by Ginger and Mary Ann. He complains that high-heeled shoes are pinching his feet, and asks them how they deal with it. They tell him to concentrate on how much the earrings are pinching his ears.
- Miami Vice: In one episode, Gina wears high heels that cause her so much pain, she can barely stand. Trudy has to support her as she walks.
- RuPaul's Drag Race: Comes up all the time, as many of the queens wear outlandish heels during the runway portion and will quickly ditch them in favor of slippers while sitting backstage during deliberation. Also, whenever the Once a Season makeover challenge involves men, they almost always struggle with the heels.
- Saved by the Bell introduces a Tomboy called Tori, who tries to doll up for a dance later in the episode. She repeatedly trips over her heels, clearly not used to walking in them.
- A Series of Unfortunate Events: In part one of book 8 (The Hostile Hospital), Esme Squalor chases the main characters through the Library of Records. She repeatedly trips due to her bladed stiletto heels and ends up using them as throwing knives against the Baudelaires.
- In an episode of Smallville, Lois tries to become a superhero of her own: "Stiletto". Her signature piece of costuming is, of course, a pair of killer heels - and she spends much of her time complaining about how hard they are to walk in, how much they hurt her feet or both.
- WWE Tough Enough's fifth season premiere featured the contestants working backstage at a WWE event. Ariane laughed "I'm doing this in heels" while working as a janitor.
- On You're the Worst, Gretchen wears her wedding high heels to a day spent on her feet at work; at the end of the episode, there's a closeup of her bloody feet as she takes them off.
- Gaia in Final Fantasy XIV wears high heel boots, to which she complains about her feet killing her after she and the rest of the party do some running around in the desert. Thancred points out that Gaia should have worn more practical footwear if she was going to walk through a desert.
- Invoked in Destroy All Humans! when reading the minds of certain women.
Woman: I'd like to meet the man who invented heels... And kill 'em.
- Jaiden Animations: The narrator, Jaiden, dislikes wearing heels, though not because they hurt, rather because she's clumsy when wearing them.
- In RWBY, during a Ballroom Blitz, Ruby finds herself at a disadvantage in a fight against Cinder because of the high heels she'd been wearing (as she favors boots, compared to her partner Weiss' Combat Stilettos), even calling them "stupid lady stilts".
Ruby: Can we have a serious discussion about how Weiss fights in these?
- Something of a Running Gag for Geek Remix whenever a character is wearing heels while doing a lot of running is mentioning how painful it must be. Most notably the main character of The Missing: J.J Macfield and the Island of Memories, who Stacy compared to the one girl who's decided she's committed to a pair of heels on a night out and refuses to take them off.
- Examined in The Try Guys' video where the four of them attempt to wear high heels in various styles and heights while out on the town without "flatting out," a play on tapping out, where they trade their heels for flats when the pain is too much. The shoes range from Zach's sensible three-inch heel ankle boots to Eugene's ridiculous six-inch stilettos (which put a hole in his laminate floor). While they like the way the shoes look, all four of them admit that their feet hurt terribly once they walked in them for any length of time and they're difficult to move and keep their balance in. Ned even accidentally faceplants when his heels get stuck on the rung of a barstool. By the end of the evening, all four of them opt to flat-out; even the ones who forgot to bring backup shoes would rather walk home barefoot than struggle in the heels.
- Justice League Unlimited: Subverted in the episode The Once and Future Thing: Weird Western Tales, after time-travelling Leaguers end up wearing the clothes of Old West bandits as disguises, Wonder Woman complains the cowboy boots she's wearing are killing her. Batman points out, "You fight crime in high heels" to which Wonder Woman replies, "High heels that fit!".
- Recess - Spinelli is entered in a Beauty Contest and so must learn to walk in heels. Vince of all people has to teach her how. Her first attempt even prompts ominous music as her legs wobble.
- The Scooby-Doo Project: While solving a mystery in the woods, Daphne complains that her feet hurt.
Velma: Well, is it our fault you wore high heels on a hiking trip?
Daphne: At least I try to look feminine!
Velma: [stunned silence]
- Another Scooby-Doo example appears in one of the "behind the scenes featurettes" from Scooby-Doo's Greatest Mysteries. Daphne complains about not being seen as smart compared to Velma, citing her straight-A average. Then Velma points out that Daphne goes around wearing pumps even when the current case puts them in the middle of a wetland.
- The Scooby-Doo Project: While solving a mystery in the woods, Daphne complains that her feet hurt.
- Wakfu: In "Miss Ugly", as part of an "ugly princess" disguise, Evangelyne has to wear high-heeled sandals. As she's totally unaccustomed to them, this results in several embarrassing slips and falls for her, including one down a full flight of stairs.