In real life, some women don't like dresses or skirts for a variety of reasons. They don't think they look good in them, they don't accentuate their figures the right way, they don't like the image they give off, long skirts and dresses are very impractical for running around (though short skirts can be very practical for active women, with some miniskirts even being explicitly designed for sportswear), they can be harder to sit down in, they're not warm enough for the climate, they're too frilly, they're too girly, the risk of a Panty Shot is higher, etc. Sometimes, they just don't like dresses with no specific reason behind it. They're just not their style.
In fiction, however, mainly two types of characters hate dresses: tomboys or Butch Lesbians who dislike "girly" stuff and Action Girls who find their looseness too cumbersome. There's often an overlap between them. Sometimes the character's belief that Real Women Don't Wear Dresses is behind their disdain for dresses and skirts. Other times they're just not used to loose-fitting, frilly garments due to their normal rough-and-tumble attitude.
A girl who doesn't like dresses or skirts will inevitably be put into one eventually. She will look nice in it, however, she will not enjoy the experience (at least not explicitly) and will often be insecure of herself.
Contrast the male Crossdresser, who challenges the same gender norms from the other direction and likes wearing dresses and skirts, but often isn't allowed to, and/or criticized for it if he does. Putting both characters through a "Freaky Friday" Flip together may have funny results.
See also Of Corset Hurts (for the common depiction in historical fiction of corsets as instruments of misogynist torture).
- Blood+: Contrasting with her sister Diva, who usually wears a Pimped-Out Dress, Saya feels very uncomfortable wearing dresses. When she's rescued by Solomon, he undresses her to bandage her wounds, and when she wakes up naked, she's shown to be as uncomfortable around him wearing only a Modesty Bedsheet as she is wearing the dress he gave her, and puts it on simply because she didn't want to be walking around naked.
- Akane from Bokura no Hentai isn't much of a tomboy anymore, but in a preschool flashback, Marika's mom mentions how she let her child wear dresses until "he" begins school because Marika hated pants. Akane's mom says her daughter is the opposite— a girl who won't wear skirts. Akane doesn't appear to be dysphoric like Marika though and she eventually outgrew her dislike of skirts.
- In Death Note Word of God states that Naomi Misora hates wearing dresses and skirts.
- The Bifauxnen Rico from Gunslinger Girl dresses in rather androgynous clothing due to her handler. In order to move unnoticed in an opera house where she's supposed to assassinate her target, Rico has to wear a dress. She complains that a dress is "too loose" for her. Justified in that she hates the idea of being restrained in any way since she used to be an Ill Girl who was bed-bound her entire life.
- Asuna Kagurazaka of Negima! Magister Negi Magi would prefer not to wear anything frilly if she can help it. She will relent if the occasion calls for it though.
- Nisekoi Tsugumi says that she avoids feminine clothes, including skirts and dresses because they are hard to fight in and are embarrassing to wear. Ironically, she becomes a Fashion Model in the epilogue.
- Sailor Uranus from Sailor Moon has "skirts" listed in her profile underthings she dislikes. She does, however, wear a skirt as her Magical Girl attire and has been shown wearing a skirt as a part of her school uniform (though she's usually depicted in the boy's pants, especially in the '90s anime).
- Kaoru in Powerpuff Girls Z is reluctant at first to become a Magical Girl because she has to wear a skirt. Ironically, Buttercup from the original series perpetually wore a dress (she obviously didn't mind dresses, just overly frilly dresses).
- Takatsuki from Wandering Son is a complicated example. She's introduced as a boyish child who wants to be seen as a boy. When she enters middle school and is forced to wear a skirt, she's miserable and embarrassed by it. Partway through middle school she begins using the male uniform, however after her trans girlfriend Nitori gets bullied for going to school in a Sailor Fuku she goes back to the normal attire. Takatsuki signed up for her high school specifically because it was a no-uniform school where she could dress in casual attire. Eventually Takatsuki becomes an androgynous Fashion Model. During this period she begins having insecurities about her gender. By the time she finishes high school, she's gone from hating skirts to liking them and no longer wants to live as a boy, though her actual gender is still vague.
- Forever from Lazarus is a nigh unkillable, superhumanly fast and strong asskicker who leads her family's military in battle, where she is willing and able to kill without hesitation or remorse. Put her in a dress, however, and she instantly turns into a self-conscious and inexperienced young woman. Her father has to talk her out of an attempt to try to ditch the dress in favor of a military uniform, and even then she grumbles about there being no way to wear her sword with it.
- Peppermint Patty from Peanuts was the first girl in the series to wear shorts. She always wears shorts and is the most tomboyish character. In 1972 her school began using a dress code and she had to wear dresses and shoes (instead of sandals) to school. The first time this occurs, she complains because she never wears dresses and punches a boy for laughing at her in a dress. She ended up going to court to abolish the dress code.
- Stone Soup: Alix refuses to wear dresses unless it's for special occasions, and even then she wears shorts underneath.
- Heart-Shaped Pancakes is a Harvest Moon: Friends of Mineral Town oneshot that starts with Ann's father tries to convince his tomboyish 11-year old daughter to wear a dress to a festival. Ann initially refuses, preferring overalls to dresses.
- In Pokémon: A Marvelous Journey, Julia has mentioned on a few occasions that she hates wearing dresses and skirts. Half of it is due to her sensory issues, and the other half of it is out of fear that someone could flip a skirt she's wearing and exposing her underwear, using it as a means to bully her.
- The Wound's Still Bleeding: In Chapter 3, Kushina learns that just because Kakashi is a trans girl doesn't mean she's a Girly Girl. She can't stand skirts or dresses. They're too uncomfortable and she also hates that most people don't wear anything underneath them. It isn't until adulthood that Kakashi comes around to the idea of maybe trying dresses.
- The tomboyish Kristy from The Babysitters Club doesn't like wearing dresses in the film incarnation, unlike her book counterpart, who doesn't particularly mind wearing them. She's embarrassed to have her friends see her wearing a dress.
- Lara Croft: Tomb Raider: Lara steps out of the shower in a towel to see her butler Hillary holding a pair of heels and a dress for her, which she is quick to dismiss.
- In The Dresden Files: Blood Rites Harry's Friend on the Force Karrin Murphy turns up to a family reunion wearing a dress, surprising Harry when he arrives to pick her up for an attack on a Black Court stronghold. She explains she hates dresses but she wanted to make her mom happy.
- Hunky Dory: Dorian's friend Rosemary, a.k.a "The Herb", doesn't like dresses but it's not the dresses themselves so much as not being allowed to get them dirty (because she likes digging and she only wears dresses on special occasions.)
- Journey to Chaos: Tiza makes a fuss whenever her team is hired as sewing dummies, ostensibly because they are mercenaries but also because she's a tomboy. It's actually rooted in a traumatic brainwashing incident in her backstory.
- Sarah from Patience and Sarah has been raised like a boy since she was nine. She's comfortable in men's clothes and seldom wears women's attire. The first time she's shown wearing a dress (which her mother lent her), she finds it embarrassing and awkward.
- The Worst Thing About My Sister: Martina, or "Marty", the main character doesn't like wearing dresses because she thinks she looks silly in them.
- The Facts of Life: Tomboy Jo was not a fan of dresses. They weren't practical enough for her.
- In The Flash, Caitlin's Killer Frost side dislikes wearing girly dresses.
- Played with on House of Anubis. While Patricia, the most tomboyish girl in Anubis House, had been seen wearing dresses willingly during the big dances in each season, she hated having to wear a frilly pink one in The Touchstone Of Ra. She wore it because Sophia thought Eddie would like it, and spent the rest of the movie rather disgruntled about it, especially when her friends teased her for it.
- Telly in Salute Your Shorts is pathological about this. In "Zeke the Plumber", the forfeit she offers if Budnick succeeds in spending a night in the clearing where Zeke is alleged to have died is that she will wear a dress for a day, a nod to her Zeke-related nightmare about being trapped in a dance hall wearing a ball gown.
- Punky Brewster was a pure tomboy and mainly wore jeans as part of her unorthodox attire. She only wore dresses out of necessity of the situation (in a Halloween episode, she's dressed as a 50s doo-wop girl in a poodle skirt). Her animated counterpart did similar.
- The Outpost: Talon is only persuaded to wear one once, and then never again (it didn't work for her).
- Sara Del Rey will wear a lot of things under the correct circumstances. And in most circumstance she has to be ready to kick anyone she thinks is not giving her enough respect, so a dress is right out...though she has been known to wear a single "flap" in imitation of a flag.
- Ivelisse Vélez rather vocally. She'll do some "girly" activities like cheer leading, or Halloween contests but if a skirt is part of the uniform don't expect her be happy about it, definitely not if she has to wear a gown, strapless dress or anything down to the knees(she also avoids bustier and heels).
- The Elder Scrolls Online: Naryu Virian is a Dark Elf assassin who teams up with the Player Character on numerous occasions. During one quest, she goes undercover wearing a very effeminate dress. The player can choose to tell her she looks good in it, which makes Naryu blush and say that though she normally hates this sort of thing, she wouldn't mind wearing something a lot more elegant for you sometimes...only to immediately backtrack on that and insist that you focus on the mission.
- One of the endings to Final Fantasy V shows that Sweet Polly Oliver Faris dislikes wearing dresses.
- In the DC Super Hero Girls short "#StreetStyle," it's Picture Day and the punkish tomboy Kara has to wear a pretty '60s-style dress to school. As in, her foster parents had the rest of her clothes sent to the laundromat, forcing Kara to wear the dress. Kara hates it. She ends up accidentally ruining it while saving people on the way to school, but Kara actually likes it better that way.
- Laney Penn from Grojband hates being girly, which includes wearing dresses. In "Queen Bee", with a pageant contest at stake, she has no choice but to enter as a contestant. She makes it clear she dislikes the idea of pageants, being viewed as a sweetheart, and is all too glad when she no longer has to wear the dress.
- Jade Chan from Jackie Chan Adventures is a supreme tomboy, who never wears anything feminine except for a few cases. When her uncle Jackie signed her up with some girl scout troop, Jade was of course very dismayed by the uniform she was expected to wear.
- Pepper Ann's tomboyish sister Moose from Pepper Ann is shown to dislike wearing dresses.
- Played with when it comes to Buttercup from The Powerpuff Girls (2016). She is the most tomboyish Powerpuff, but like her sisters, the only outfit she wears most of the time is a green dress. However, in the extended intro, Buttercup is annoyed at wearing a frilly "pretty skirt."