Cross dressing movies and TV shows

The list contains the best, new and most relevant cross dressing movies ordered by relevance. The recommendation service has sorted out realistic, humorous, feel good, entertaining, captivating and independent film films and TV shows about / with cross dressing, gender, gender bending, transvestite, gay, love and romance, lgbt, friendship, hidden identity and disguise plots mostly in Comedy, Drama and Romance genres shot in USA, UK, Canada and other countries.
cross dressing
 958
cross dressing movies
TOP 10 movies tagged as cross dressing: Unconditional (2012), Sorority Boys (2002), Just One of the Guys (1985), Bosom Buddies (1980), She's the Man (2006), White Chicks (2004), 100 Girls (2000), Just One of the Girls (1993), Work It (2012), The 1st Shop of Coffee Prince (2007).

List of cross dressing movies

Watch Trailers From This List to Choose a Movie
 6.6
 772
Unconditional (2012)
Genre: Drama, Thriller
Country: UK
Duration: 92 min.
Story: A psychological romantic drama about teenage twins Owen and Kristen who fall under the sway of a charismatic young loan shark who offers love to one of them but on one condition.
Style: realistic, serious, unusual plot structure, sexy, psychological thriller ...
Audience: teens
Plot: cross dressing, homosexual, brother sister relationship, gay, manipulation, sexual obsession, twins, gay interest, lgbt teen, love and romance, obsession, family relations ...
Time: 21st century
Place: england
Is relevant ?
 5.4
 16K
Sorority Boys (2002)
Genre: Comedy
Country: USA
Duration: 93 min.
Story: Three friends who head the Social Committee in a frat house, called KOK (Kappa Omicron Kappa), are charged with stealing money their fraternity has been saving for a cocktail cruise at the end of the semester, the one that guarantees them a spot at ...
Style: humorous, funny, not serious, slapstick, teen ...
Audience: teens
Plot: cross dressing, college, student life, farce, hidden identity, high school, sorority, stereotypes, stupidity, fish out of water, transvestite, comedy of errors ...
Time: 21st century
Place: usa
Is relevant ?
Just One of the Guys (1985)
Genre: Comedy, Romance
Country: USA
Duration: 100 min.
Story: When Terry Griffith loses her high school's writing competition, she's convinced that it's because she's a girl. So Terry decides to change high schools and pose as a boy to prove her point. Her brother, Buddy, helps her pass as ...
Style: entertaining, feel good, not serious, humorous, teen sex comedy ...
Audience: teens, chick flick, family outing, girls' night, date night
Plot: cross dressing, high school, gender disguise, adolescence, gender bending, college, sexism, prom, hidden identity, switching roles, coming of age, gender bender ...
Time: 80s, year 1985
Place: california, phoenix arizona, arizona, tucson arizona
Is relevant ?
Bosom Buddies (1980)
Genre: Comedy
Country: USA
Duration: 30 min.
TV show
Story: Bosom Buddies is an American sitcom starring Tom Hanks and Peter Scolari created by Robert L. Boyett, Thomas L. Miller and Chris Thompson. It ran from 1980 to 1982 on ABC and in reruns in the summer of 1984 on NBC. The show features the ...
Style: sitcom, buddy comedy, not serious, humorous, realistic ...
Audience: kids, chick flick, girls' night, date night
Plot: cross dressing, gender bending, hotel, friendship, physical appearance, workplace romance, showbiz, lifestyle, workplace, battle of the sexes, performer's life, hidden identity ...
Time: 20th century, 80s, 90s
Place: usa, new york
Is relevant ?
 6.4
 174K
She's the Man (2006)
Genre: Comedy, Romance, Sport
Country: USA, Canada
Duration: 105 min.
Story: Viola Johnson is in a real jam. Complications threaten her scheme to pose as her twin brother, Sebastian, and take his place at a new boarding school. She falls in love with her handsome roommate, Duke, who loves beautiful Olivia, who has fallen for ...
Style: romantic, feel good, funny, teen, romantic comedy ...
Audience: teens, chick flick, girls' night, date night, kids ...
Plot: high school, teenager, soccer, cross dressing, tomboy, roommate, teenage love, teen romance, high school life, teenage life, hidden identity, gender disguise ...
Time: 2000s, 21st century
Place: usa, london
Is relevant ?
 5.8
 162K
White Chicks (2004)
Genre: Comedy, Crime
Country: USA
Duration: 109 min.
Story: Two FBI agent brothers, Marcus and Kevin Copeland, accidentally foil a drug bust. As punishment, they are forced to escort a pair of socialites to the Hamptons, where they're going to be used as bait for a kidnapper. But when the girls realize ...
Style: humorous, funny, satirical, parody, teen ...
Audience: teens, date night, chick flick, girls' night
Plot: cross dressing, fbi, dumb, fish out of water, working undercover, gender bending, buddy cop, gender disguise, undercover, sisters, stereotypes, chase ...
Time: year 2004, future, 2000s, 21st century
Place: usa, new york
Is relevant ?
 5.8
 24K
100 Girls (2000)
Genre: Comedy, Romance
Country: USA
Duration: 94 min.
Story: This sexy, teen-comedy is about a freshman, Matthew, at college who meets his dream girl in a dorm elevator during a blackout. He never sees her face, but instantly falls in love. In the morning, the power is restored, but the "dream girl" ...
Style: teen sex comedy, sex comedy, romantic, talky, teen ...
Audience: teens, chick flick, date night
Plot: college, youth, fall in love, elevator, college life, high school, battle of the sexes, man disguised as a woman, sex in an elevator, lust, attempted rape, misogynist ...
Time: 90s, 2000s
Is relevant ?
Just One of the Girls (1993)
Genre: Comedy
Country: Canada, USA
Duration: 91 min.
Story: Chris has to change school to attend a music program, but a bully named Kurt is going to make his life impossible so he decided to dress as a girl to avoid this. Taking advantage of his condition he became (girl-)friend with Marie, and fell in love ...
Style: realistic, humorous, semi serious, teen sex comedy, entertaining ...
Audience: date night, teens, chick flick
Plot: fall in love, teenage life, cross dressing, high school, gender bending, youth, switching roles, cheerleading, friendship, college, teenage love, high school life ...
Time: 90s
Is relevant ?
 3.1
 976
Work It (2012)
Genre: Comedy
Country: USA
TV show
Story: Work It is an American television sitcom that ran on ABC from January 3 to January 10, 2012 as a mid-season replacement for the canceled Man Up!. The series is set in St. Louis, and is about two men who must dress as women in order to keep a job in ...
Style: sitcom, not serious, realistic, entertaining, feel good ...
Plot: cross dressing, man dressed as woman, hidden identity, buddies, workplace situations, workplace, dishonesty, gender, family relations, disorder, gender bending, physical appearance ...
Time: 21st century
Place: usa, st. louis missouri
Is relevant ?
The 1st Shop of Coffee Prince (2007)
Genre: Comedy, Drama, Romance
Country: South Korea
Duration: 55 min.
TV show
Story: Han-gyeol is a smart young man who hates to be tied down to one career in his life. Abhorring the idea of joining the family business, he is ordered by his grandmother to manage a cafe. Unable to disobey his grandmother, he reluctantly takes over ...
Style: romantic, dorama, feel good, touching, inspirational ...
Plot: tomboy, cross dressing, coffee shop, friendship, gender disguise, love triangle, love and romance, class differences, sister sister relationship, romantic friendship, male female relationship, mistaken for being gay ...
Place: seoul, korea
Is relevant ?
 8.7
 5K
Veneno (2020)
Genre: Biography, Drama
Country: Spain
Duration: 421 min.
TV show
Story: Adored for her charisma and her free, explicit and fun way of expressing herself, La Veneno gained popularity thanks to her television appearances in the 90s. However, her life and especially her death remain an enigma. 'Venom' is a series ...
Style: heartbreaking, touching, captivating, queer cinema, complex
Audience: chick flick
Plot: transsexual, gender, cross dressing, transgender, artists and showbiz, lgbtq, lgbtqi, celebrity, gay, loneliness, secret, life philosophy ...
Is relevant ?
For You in Full Blossom: Ikemen Paradise (2007)
Genre: Comedy, Drama
Country: Japan
Duration: 54 min.
TV show
Story: Hanazakari no Kimitachi e: Ikemen Paradise, also known as Ike-para, is a Japanese drama produced by Fuji Television and first aired on July 3, 2007. It is based on the comic by Hisaya Nakajo, published in English as Hana-Kimi. Filming locations ...
Style: light, dorama, inspirational, emotional, humorous ...
Plot: cross dressing, boys' school, friendship, rivalry, love, dormitory, everyday life, frustration, athlete's life, love triangle, high school, private school ...
Place: japan
Is relevant ?
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After the Ball (2015)
Genre: Comedy
Country: Canada
Duration: 101 min.
Story: After the Ball, a retail fairy tale set in the world of fashion. Kate's dream is to design for couturier houses. Although she is a bright new talent, Kate can't get a job. No one trusts the daughter of Lee Kassell, a retail guru who ...
Style: feel good, semi serious, humorous, funny, romantic ...
Audience: girls' night, teens
Plot: fashion, cinderella story, cross dressing, female protagonist, happy ending, love and romance, father daughter relationship, good versus evil, dream, haute couture, family relations, parents and children ...
Time: 21st century
Place: new york, usa, montreal
Is relevant ?
 5.6
 102K
The Hot Chick (2002)
Genre: Comedy, Fantasy
Country: USA
Duration: 104 min.
Story: Not only is Jessica Spencer the most popular girl in school -- she is also the meanest. But things change for the attractive teen when a freak accident involving a cursed pair of earrings and a chance encounter at a gas station causes her to switch ...
Style: funny, teen, entertaining, humorous, not serious ...
Audience: teens, chick flick, girls' night, date night, teen drama
Plot: body swapping, high school, cross dressing, prom, switching roles, cheerleading, gender, popular girl, teenage life, dumb, gender bending, switching bodies ...
Time: year 2002, 2000s, 1st century b.c., 21st century
Is relevant ?
Twelfth Night or What You Will (1996)
Genre: Comedy, Drama, Romance
Country: Ireland, UK
Duration: 134 min.
Story: Shakespeare's comedy of gender confusion, in which a girl disguises herself as a man to be near the count she adores, only to be pursued by the woman he loves.
Style: period piece, stylized, light, feel good, humorous ...
Audience: girls' night, date night
Plot: cross dressing, shakespeare, twins, mistaken identity, comedy of errors, beach, disguise, love triangle, sea disaster, disorder, couples, fall in love ...
Time: 19th century, year 1996, 1890s, 1800s, victorian era
Place: cornwall, britain
Is relevant ?
 6.0
 68
Delight (2013)
Genre: Drama
Country: Czech Republic
Duration: 111 min.
Story: The film's main theme is obsession. An obsession with love, with art, originality, copying, with success, money and... with oneself. Sooner or later, if we lose our rational upper hand over it and let ourselves be dragged down by it, every ...
Style: unusual plot structure, thought provoking, captivating
Plot: art, obsession, female nudity, transvestite, female protagonist, sex, cross dressing, suicide, death, twins, gay, troubled relationship ...
Is relevant ?
 5.2
 631
Luminarias (1999)
Genre: Comedy, Romance
Country: USA
Duration: 100 min.
Story: Welcome to Luminarias-where hot spicy dish gets served up with a Latin twist by four successful friends from East LA...with very discriminating taste in men! When separated divorce attorney Andrea finds herself guilty of falling for her white and ...
Style: independent film, semi serious, realistic, talky, touching ...
Audience: girls' night, date night
Plot: glbt, restaurant, family relations, racism, friendship, couples, thirtysomething life, transvestism, friends, feminism, buddies, gender ...
Time: 90s
Place: los angeles, california, usa
Is relevant ?
A Double Identity (2010)
Genre: Drama
Country: Mexico
Duration: 60 min.
TV show
Story: Niña de mi Corazón is a teen Mexican telenovela produced by Televisa and Telefe adapted from Pedro Damian's 1997 Mi Pequeña Traviesa, that premiered on March 8, 2010 and ended on July 9, 2010. Damian was also the producer of this telenovela.
Style: entertaining, captivating, disturbing, telenovela
Plot: gender disguise, employer employee relationship, con trick, double life, hotshot lawyer, pretending to be someone else, law firm, sexism, male female relationship, female lawyer, gender issues, cross dressing ...
Is relevant ?
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 7.1
 289K
Mrs. Doubtfire (1993)
Genre: Comedy, Drama
Country: USA
Duration: 125 min.
Story: Loving but irresponsible dad Daniel Hillard, estranged from his exasperated spouse, is crushed by a court order allowing only weekly visits with his kids. When Daniel learns his ex needs a housekeeper, he gets the job -- disguised as an English ...
Style: feel good, touching, funny, hilarious, light ...
Audience: family outing, kids, family friendly, teens, girls' night ...
Plot: cross dressing, divorce, nanny, comedy of errors, children, kids and family, transvestite, gender, family relations, custody battle, single father, gender disguise ...
Time: 90s, 20th century
Place: san francisco, bay area, california, usa
Is relevant ?
Garbage, the City and Death (2012)
Genre: Drama
Country: Czech Republic
Duration: 74 min.
Story: Romi (Gabriela Mícová), a prostitute, is anything but successful at her job: she is of far too gentle a nature for her clients. The more obstinately she is pushed to the streets by her pimp Franz (Stanislav Majer), the closer she is to a complete ...
Style: compassionate, captivating, realistic, serious, disturbing ...
Plot: prostitute, female impersonator, prostitution, man dressed as woman, transvestite, family relations, gay interest, manipulative person, nightclub, dysfunctional family, domestic violence, pimp ...
Time: 21st century
Place: europe, central europe, prague
Is relevant ?
Men Cry Bullets (1998)
Genre: Comedy, Drama
Country: USA
Duration: 105 min.
Story: A young man wants to be a female impersonator, but gets mocked in his very first performance by a fierce older woman. He finds out where she lives and goes to her house expecting an apology. Instead, she locks him in her shed and rapes him. It makes ...
Plot: love triangle, transvestite, male pubic hair, satire, female rapist, dark humor, domestic violence, cross dressing, female on male rape, gun, pubic hair
Is relevant ?
An Unsuitable Job for a Woman (1982)
Genre: Crime, Drama, Mystery
Country: UK
Duration: 94 min.
Story: After the suicide of her friend and employer, who has been teaching her to be a detective, Cordelia Gray (Pippa Guard) takes over his business and begins an investigation of the apparent suicide of the son of a businessman. When the suicide turns ...
Style: detective, independent film
Plot: private investigator, mysticism, murder investigation, suspicion, private investigation, mysterious death, twenty something, private detective, female protagonist, cross dressing, accident, murder ...
Time: year 1982
Is relevant ?
Surrender Dorothy (1998)
Genre: Comedy, Drama, Romance
Country: USA
Duration: 87 min.
Story: Trevor is a busboy who is so terrified of women that he takes in a young man addicted to heroin and then uses the drug to manipulate, coerce, and terrorize him into becoming "Dorothy", his twisted concept of the "ideal ...
Style: independent film, tense, mind bending, captivating, serious ...
Plot: drug abuse, transgender, lgbtq, drug addiction, glbt, sadomasochism, manipulation, gender bending, obsession, mirror, injection, letter ...
Time: 90s, 20th century
Place: usa, philadelphia
Is relevant ?
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Back Street Girls: Gokudols (2019)
Genre: Action, Comedy, Crime
Country: Japan
TV show
Story: Tough gangland retribution takes a disturbingly bright, shiny turn in this insanely guilty pleasure about 3 yakuzas who, as repayment for their failures, must undergo major surgery and become … a hot female idol trio! So what happens when they ...
Style: entertaining, satirical, captivating, semi serious
Plot: yakuza, idol, mafia, pop group, gangster, moll, pop star, gangster boss, music band, music, organized crime, pop singer ...
Is relevant ?
 6.7
 26K
Albert Nobbs (2011)
Genre: Drama, Romance
Country: USA, Ireland, UK, France
Duration: 113 min.
Story: Albert Nobbs struggles to survive in late 19th century Ireland, where women aren't encouraged to be independent. Posing as a man, so she can work as a butler in Dublin's most posh hotel, Albert meets a handsome painter and looks to escape ...
Style: sad, touching, sincere, period piece, stylized ...
Plot: gender, cross dressing, lesbian, loneliness, master and servant, woman dressed as man, maid, hotel, servant, gender disguise, death, relationships ...
Time: 19th century, 1890s, victorian era, 1800s, year 2011
Place: ireland, dublin ireland, england, britain, europe
Is relevant ?
Good-bye Cruel World (1982)
Genre: Comedy
Country: USA
Duration: 100 min.
Story: The story involves newscaster Rodney Pointsetter (Shawn) who is so depressed between his job and his family that he tries to make a film about his life, which he intends to culminate with his own suicide. It is often interrupted with irrelevant ...
Style: slapstick comedy, dark comedy, independent film, slapstick, spoof
Plot: teenager, suicide, vulgar, car crash, divorce, television, neighbor, death, absurd humor, cross dressing, sumo, satire ...
Is relevant ?
 7.2
 2K
Love Stage!! (2014)
Genre: Animation, Comedy, Romance
Country: Japan
TV show
Story: Izumi was born in a family of celebrities. His father is a singer, his mother an artist, his older brother the lead vocalist for the popular band Crashers. Izumi himself, however, is just a nerdy college student. He loves the manga "Magical ...
Style: yaoi, anime, entertaining, feel good, light ...
Plot: gay, showbiz, cross dressing, art, lgbt, lifestyle, singer, love, escapades, couple relations, idol, family relations ...
Is relevant ?
Everybody's Talking About Jamie (2021)
Genre: Biography, Comedy, Drama, Musical
Country: UK, USA
Duration: 115 min.
Story: Feature film adaptation of the musical about a teenager from Sheffield, England who wants to be a drag queen.
Style: lgbt cinema, emotional, psychological, touching, social ...
Audience: teens, chick flick, date night, teen drama
Plot: lgbt, female impersonator, cross dressing, drag queen, lgbtq, gay student, transsexual, gay, gay slur, gay interest, life is a bitch, friendship ...
Time: 2020s
Place: britain, united kingdom, england, yorkshire
Is relevant ?
 2.9
 218
Love Feast (1969)
Genre: Comedy
Country: USA
Duration: 63 min.
Story: Mr. Murphy, a photographer, lures models to his house on the pretense of legitimate modelling work, and then busies himself bedding them. After a while, his bedroom has gotten pretty crowded and he's exhausted, so he snags a taxi cab driver to ...
Style: sex comedy, independent film
Plot: photo model, drag, photographer, humiliation, dominatrix, cross dressing, director, lesbian sex, female pubic hair, nudity, fetishism, orgy ...
Is relevant ?
To Wong Foo Thanks for Everything, Julie Newmar (1995)
Genre: Comedy, Drama
Country: USA
Duration: 109 min.
Story: Three New York drag queens on their way to Hollywood for a beauty pageant get stranded in a small Midwestern town for the entire weekend when their car breaks down. While waiting for parts for their Cadillac convertible, the flamboyant trio shows ...
Style: road movie, cult classic, entertaining, sweet, light ...
Audience: chick flick, adult
Plot: gay, transvestism, gender bending, drag queen, small town, friendship, cross dressing, road trip, on the road, lgbt, transgender, culture clash ...
Time: 20th century, 90s
Place: nebraska, usa, new york
Is relevant ?
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