Embarrassingly Dresslike Outfit

"I look like my great-aunt Tessie! I smell like my great-aunt Tessie! Murder me, Harry!"

Worf: These uniforms are ridiculous. They look like dresses!
William Riker: Mr. Worf, that is an outmoded, sexist attitude! Besides, you look good in a dress.

— Star Trek: The Next Generation, "Liaisons"

While anyone may wear a dress, in most cultures, they're generally regarded as a garment for women. For some male characters, this extends to anything that could vaguely resemble a dress or skirt, such as a bathrobe, nightgown, or a kilt.

The character will often have to wear the outfit for a special occasion, or because it's the only clean outfit, or for some other reason that's beyond his control. Expect him to complain about having to wear a "dress", to which someone else will reply something along the lines of "It's not a dress, it's an X. Lots of men wear X."

Usually played for Cringe Comedy and is Always Male. For the Distaff Counterpart, see Unwillingly Girly Tomboy. If he really is wearing women's clothes, see Disguised in Drag, Dragged into Drag, and Unplanned Crossdressing (and if he tries to pretend he isn't, he may use Insistent Terminology or a Less Embarrassing Term). Contrast Crossdresser and its subtropes Creepy Crossdresser and Wholesome Crossdresser for when a man is deliberately trying to dress like a woman. Compare Red Sock Ruins the Laundry, Pink Is for Sissies, Uncool Undies, Bad Job, Worse Uniform, Forced into Their Sunday Best, and Goofy Suit for more tropes about embarrassing clothes. Contrast Hates Wearing Dresses and Lady Legionnaire Wear.

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Examples:

Films — Animation

• The Emperor's New Groove: When Kronk's shoulder devil and angel first appear, the shoulder devil points out the reasons why Kronk shouldn't trust the angel, including a disparaging comment about his heavenly robe being a dress.
  Devil Kronk: Listen up, big guy! I've got three good reasons why you should just walk away. Number one: look at that guy! He's got that sissy stringy music thing.
  Angel Kronk: We've been through this. It's a harp, and you know it.
  Devil Kronk: Oh, right. That's a harp... and that's a dress.
  Angel Kronk: Robe!

Films — Live-Action

• Harry Potter and the Goblet of Fire: In the film's rendition of the leadup to the Yule Ball, Ron receives a package from his mother and finds what appears to be an antique dress inside. He at first thinks it's meant for Ginny, only for Hermione to tell him that it's dress robes, which gets everyone laughing at him. Just before the Yule Ball, he's looking at himself in the mirror after putting on the dress robes, aghast at how horrible they look and how Harry's look in comparison. (Harry's robes vaguely resemble a Muggle tuxedo.)
  Ron: Bloody hell, bloody hell, bloody hell...
  [Harry walks into the room in his dress robes and freezes at seeing Ron, while Ron does an Eye Take at Harry]
  Ron: What are those?! What are those?!
  Harry: My dress robes.
  Ron: Oh, they're alright! No lace, no dodgy little collar!
  Harry: Well, I suspect yours are a bit more traditional...
  Ron: Traditional?! They're ancient!
• Night at the Museum: Battle of the Smithsonian: Kah Mun Rah repeatedly insists that his outfit is not a dress, it's a tunic.
  Kah Mun Rah: It was the height of fashion 3000 years ago, I assure you.

Literature

• Dirty Bertie: In "Wedding!", Bertie is invited to his second cousin's wedding. Since the groom is Scottish, all the men are asked to wear kilts, but Bertie doesn't want to wear one, since he thinks they look too "skirty".
• Harry Potter: Wizards traditionally wear robes (think priest robes) and under normal circumstances, this is not seen as unmanly. However in the fourth book, there's going to be a dance and they need dress robes, or robes for formal occasions. Most of them look OK, but poor Ron—constrained by poverty and forced to get something second-hand—gets "something that looked to Harry like a long, maroon velvet dress. It had a moldy-looking lace frill at the collar and matching lace cuffs."
  Harry, Ron, Seamus, Dean, and Neville changed into their dress robes up in their dormitory, all of them looking very self-conscious, but none as much as Ron, who surveyed himself in the long mirror in the corner with an appalled look on his face. There was just no getting around the fact that his robes looked more like a dress than anything else. In a desperate attempt to make them look more manly, he used a Severing Charm on the ruff and cuffs. It worked fairly well; at least he was now lace-free, although he hadn't done a very neat job, and the edges still looked depressingly frayed as the boys set off downstairs.
  • Played with earlier in the same book: before the Quidditch World Cup, the protagonists overhear a man in ladies' sleepwear arguing with his friend who begs him to put on pants.
    "I like a nice healthy breeze 'round my privates, thanks."
• Mick Harte Was Here: A retroactive example; Mick is horrified to find out that he once wore a christening gown as a baby and yells at his mom for "taking him to church in a dress". He's so upset by it that he overcompensates by wearing a black motorcycle-themed shirt and camouflage pants every week to Sunday school for the rest of the year. Eventually, he starts wearing it every day at regular school too. The school psychologist tells his mom it's his way of balancing out the "trauma of being paraded around in public wearing ladies' sleepwear."
• The Midnight Gang: When Tom is admitted into a hospital, he is embarrassed because the only available nightwear is a pink nightie.

Live-Action TV

• Game of Thrones: In "The Night Lands", Theon Greyjoy travels to the Iron Islands to propose to his father Balon that they form an alliance with Robb Stark against the Lannisters. Balon sees Theon's stylish Northern-style clothes and asks, "Was it Ned Stark's pleasure to make you his daughter?", viewing them as a sign of Theon not being much of an Ironborn. He rejects the offer and decides to attack the North instead, placing Theon's sister in command.
  Theon: [in shock] She [Yara] can't lead an attack!
  Balon: And why not?
  Theon: You're a woman!
  Yara: You're the one in skirts.
• Happy Days: In "Arnold's Wedding", Arnold, who is Japanese, is getting married. The guests all wear kimonos, which Fonzie and Potsie are embarrassed about, thinking they look like dresses.
• Star Trek: The Next Generation: In "Liaisons", Worf complains about the long tunics he and his coworkers must wear on formal occasions, stating they look like dresses. Riker thinks that the belief men can't wear such garments is sexist, and besides, he looks good in a "dress".
• Wishbone: In "Rushin' to the Bone", Wishbone auditions to be the new "Mr. MacPooch", the ostensibly Scottish mascot for his brand of kibble. He is extremely miffed at having to wear a kilt for the role, repeatedly calling it "a dress".

Video Games

• Living Books: Implied for their adaptation of the Arthur book "Arthur's Teacher Trouble". When Mr. Ratburn's pants are replaced with a kilt, he looks shocked, but it's unclear whether it's because of the kilt or because of the clothes simultaneously changing.
• In Warcraft III, poking the Dreadlord enough will have him adamantly state "No, this is not a dress! It's the standard Dreadlord uniform!". This is a bit of an Orphaned Reference however; the Dreadlord is wearing a suit of plate armor in the release version, but the beta version had him in a very dress-like robe. The voiceline was never changed or removed to match the newer model.

Western Animation

• In the Archie's Weird Mysteries episode "The Day the Earth Moved", Archie's father wakes him up for the Andrews family tradition one day in late March. This involves them dancing in kilts, which Archie hates, considering a kilt "a skirt by any other name."
• Another "kilt" example occurs in the DuckTales (1987) episode "Once Upon a Dime." Scrooge, at this point a poor Scottish immigrant, draws the attention of a policeman, who objects to his wearing a skirt in public. ("It's a kilt!") However, when Scrooge's case goes to trial, it turns out that the judge is Scottish (and is also wearing a kilt). Offended, he sentences the policeman to wear an actual skirt for thirty days.
• In one episode of The Fairly OddParents!, Timmy's mother makes him wear a kilt, but he doesn't like it and calls it a skirt.
• Jackie Chan Adventures: In Season 2, while Shendu's spirit is possessing Valmont's body, they both start wearing a "sorcerer's robe" which Valmont finds humiliating, thinking it looks like an unmanly dress. It doesn't help at all when their henchmen trio (Finn, Ratso, Chow) all make mocking compliments about how pretty Shendu/Valmont looks while wearing it.
• The Loud House: In "Broadcast Blues", when Rusty Spokes is disguised as a woman, he complains about having to wear a "dress", even though what he's wearing is actually a pantsuit.

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