Are there "Man in a dress" jokes?

Browse movies, tv shows, books and more with "Man in a dress" jokes.
A general category for jokes that involve men dressing/acting in traditionally feminine ways or being gnc (gender non-conforming) being used as a joke or for shock value. Not to be confused with transmisogyny, or calling trans women men in dresses.
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Movie • 2022 Report
Yes
86
No
12
49
DK6407
A male character is swapped into a salsa dress, but this is played off as absurdist humor rather than misogyny.
Yes
79
No
4
25
CobaltCosmos
One character, unfortunately a victim, is found postmortem to be AMAB, which surprises many characters seeing as they presented as female. While this is very important to the plot and even ties into the motive for why they were murdered (without necessarily implying that their killer did so for transphobic reasons, at least not consciously), the presentation leans on certain tropes (ex. the character realizing this putting the fact quite crudely while panicking, one character initially acting calm while recounting the situation before suddenly unleashing a long "WHAT?", and a third party who was recently revealed as a serial killer of only men regretting not being the one to kill them), and a character who refers to something resembling this character later as feminine is treated as strange. On top of this, one female character (coincidentally the person investigating the body of previous) is also very muscular and broadly built, and catches a LOT of shit for it, even by the protagonist's thoughts.
TV Show • 1994 Report
Yes
71
No
1
20
SiRenfield
Chandler’s “father” is either a trans woman or a VERY convincing drag queen ,but either way a good chunk of the humor relies on this
Movie • 1975 Report
Yes
65
No
3
15
mmiileesss
specifically "i thought it was the real thing"
TV Show • 2019 Report
Yes
59
No
11
16
Anonymous
Not so much jokes, but Jules gets a few hate comments for being transgender
Movie • 1994 Report
Yes
58
No
0
28
Anonymous
The main plot "reveal" is that the villain is a trans woman, this is met with disgust and misgendering, entirely played for laughs.
TV Show • 2020 Report
Yes
56
No
8
4
VegaF8
A shapeshifter is sometimes unable to maintain their form and reverts to their base, masculine presenting form while still in feminine clothes. This is treated as a joke in some scenes.
Movie • 2016 Report
Yes
56
No
3
19
marabars
in a gorey way yes, art wears a naked woman's body as a suit
Movie • 1989 Report
Yes
55
No
1
9
HeatherEhch
A character says that guys being caught drinking mineral water is akin to "wearing a dress"
TV Show • 2005 Report
Yes
52
No
3
16
Mc1s23
Sokka trains with the Kyoshi warriors, a group of warriors who are all women, who make wearing their uniform a requirement for training. The leader convinces him that he should be proud to wear it, but he is then immediately teased for wearing it by a different character waking by.
TV Show • 1997 Report
Yes
52
No
3
1
jdpamv
"Midget in a bikini" is a nonconformity joke, as far as humor about trans women goes Ms. Garrison fits the bill.
TV Show • 2011 Report
Yes
52
No
4
Anime • 2006 Report
Yes
50
No
1
16
Atlus
Haruhi's father/mother (genderfluid) is often used as a "man in a dress" joke and is often used as a transphobic joke against him, along with multiple slurs (ex., Tr/nny) because of him wearing a dress when he's on screen
Movie • 1991 Report
Yes
48
No
11
15
TheCassandraComplex
The movie handles transgender issues in a clumsy, dated way that can come off comical. The depiction of Buffalo Bill, a serial killer who is crafting himself a woman-suit, is often parodied. However, the film’s intention was not for this character’s behavior to be comedic.
TV Show • 2009 Report
Yes
46
No
3
5
vermin
The dean often wears feminine clothes and is made fun of for it. There are also a few other comments by characters that imply they only see supporting trans people as a way to earn brownie points rather than a legitimate issue. Troy and Pierce are manipulated into wearing “lady’s pantsuits” for laughs as well.
Movie • 2020 Report
Yes
45
No
0
15
Idontcaretofindagoodusername
In the lyrics of "Gee Officer Krupke" there is a line that says "my sister wears a mustache, my brothers wears a dress, goodness gracious thats why Im a mess".
Movie • 1993 Report
Yes
45
No
2
15
thespianscreed
The entire premise of the movie, a man dressing up as an elderly woman, is played for laughs.
Anime • 2012 Report
Yes
44
No
2
11
SOSCYBERSLAVE
In part 2 the main protagonist dressed as a woman to try and trick the enemy into letting him inside of a base, so yes? [Tequila Joseph]
TV Show • 2005 Report
Yes
43
No
24
Movie • 2004 Report
Yes
42
No
0
20
Littleolme
The Big Bad Wolf, who wears a dress, is called "gender confused" by the Fairy Godmother. Doris, who is a woman but happens to have some traditionally "masculine" traits like deep voice, facial features and body build, is treated as ugly and not fully passing.
Movie • 1999 Report
Yes
39
No
7
7
Vyctor
Not exactly a joke, but at one point Janet gives Susanna a bottle of nail polish saying she got it from “ a transvestite in the mens ward”
Movie • 2022 Report
Yes
38
No
4
10
TFMD
The shark is a big tough-guy character who dresses as a woman in one scene. His appearance and behavior are played for laughs: he speaks in falsetto, pretends to be pregnant and in labor, etc.
TV Show • 2011 Report
Yes
38
No
8
3
Mandycandyland
Probably at some point with the theatre troupe.
TV Show • 2005 Report
Yes
37
No
22
4
TheLittlestTeacup
Not “jokes” necessarily but some unsubs dress in woman’s clothing. Most of these characters are not actually queer in any way but it may feel a bit uncomfortable if you’re trans. It didn’t bother me (trans) but if it bugs you that’s totally valid.
TV Show • 2009 Report
Yes
37
No
0
6
Delaney.cohenn
In either season 2 or 3, Puck comes in dressed in a wig and dress which is played for laughs.
Movie • 1960 Report
Yes
36
No
3
11
SiRenfield
Not “jokes” but this is on the most infamous examples of the killer cross-dresser trope (that might warrant its own category in the future though)
TV Show • 2005 Report
Yes
35
No
0
6
Jethro
Ted shows up wearing a dress in one episode, it's not a joke as in "it's funny because he's wearing a dress" but rather an inside joke between the characters, could potentially be upsetting though
Movie • 2004 Report
Yes
35
No
0
10
JayHay
That's it, that's the movie. But one thing that can be appreciated is that they gain a new perspective of what women have to deal with on a daily basis. The film's plot is two guys going undercover as white women in a university setting
Movie • 2000 Report
Yes
34
No
2
16
Sid
There’s a transphobic portrayal of a trans woman
TV Show • 1989 Report
Yes
33
No
4
5
hotfish
There's Something About Marrying ending