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 humorous, realistic, feel good, sexy, funny and entertaining films and TV shows about / with cross dressing, gender bending, gender, hidden identity, disorder, dishonesty, runaway, gender disguise, mentor and romance plots mostly in Comedy, Romance and Drama genres shot in USA, UK, Japan and other countries.
cross dressing
 779
cross dressing movies
TOP 10 movies tagged as cross dressing: She's the Man (2006), Sorority Boys (2002), White Chicks (2004), Mrs. Doubtfire (1993), Just One of the Guys (1985), Tootsie (1982), Ouran High School Host Club (2006), Bosom Buddies (1980), Mulan (1998), You Are Beautiful (2009).

List of cross dressing movies

 6.3
 146K
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: feel good, romantic, humorous, funny, realistic ...
Audience: teens, teen comedy, date night, girls' night, chick flick
Plot: teenager, cross dressing, teenage love, high school, high school life, romance, teen romance, tomboy, roommate, hidden identity, sport, lookalikes ...
Time: 21st century, contemporary, 2000s, 80s
Place: usa, london, new jersey
Is relevant ?
 5.5
 14K
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, idiotic, not serious, sex comedy, funny ...
Audience: teens, teen comedy, girls' night
Plot: cross dressing, college, sorority, student life, hidden identity, farce, fish out of water, comedy of errors, fall in love, gender bending, dishonesty, buddies ...
Time: 21st century, contemporary
Place: usa
Is relevant ?
 5.6
 132K
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, idiotic, funny, satirical, ridiculous ...
Audience: teens, date night, girls' night
Plot: cross dressing, fish out of water, working undercover, special agents, gender bending, undercover, fbi, crossdressing, gender, gender disguise, crimes, disorder ...
Time: contemporary, 21st century, 2000s
Place: usa, new york
Is relevant ?
 7.0
 247K
Mrs. Doubtfire (1993)
Genre: Comedy, Drama, Family
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, humorous, light, sentimental ...
Audience: family outing, date night, kids, girls' night
Plot: family, comedy of errors, cross dressing, nanny, divorce, family relations, kids and family, hidden identity, custody battle, gender bending, parenthood, actor playing female role ...
Time: 90s, 20th century, 1990s
Place: san francisco, usa
Is relevant ?
Related movie lists
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: feel good, humorous, not serious, entertaining, realistic ...
Audience: teens, teen comedy, girls' night, date night, chick flick
Plot: cross dressing, high school, switching roles, hidden identity, sexism, adolescence, college, romance, goofy hero, disorder, fish out of water, school ...
Time: 80s
Place: california, tucson arizona, arizona, phoenix arizona, new jersey
Is relevant ?
 7.4
 98K
Tootsie (1982)
Genre: Comedy, Drama, Romance
Country: USA
Duration: 116 min.
Story: When struggling, out of work actor Michael Dorsey secretly adopts a female alter ego -- Dorothy Michaels -- in order to land a part in a daytime drama, he unwittingly becomes a feminist icon and ends up in a romantic pickle.
Style: witty, humorous, feel good, touching, light ...
Audience: date night, girls' night
Plot: cross dressing, gender bending, actress, love, love triangle, actor, gender disguise, romance, love and romance, theatrical agent, impersonation, double life ...
Time: 80s, 20th century, year 1982
Place: new york, usa, manhattan new york city, california
Is relevant ?
Ouran High School Host Club (2006)
Genre: Animation, Comedy, Romance
Country: Japan
Duration: 24 min.
TV show
Story: Ouran High School Host Club is a manga series by Bisco Hatori, serialized in Hakusensha's LaLa magazine between the September 2002 and November 2010 issues. The series follows Haruhi Fujioka, a scholarship student at Ouran High School, and the ...
Style: romantic, feel good, touching, humorous, realistic ...
Audience: teens
Plot: cross dressing, rich and poor, teenage life, society, debt, high school, gender bending, high school hunk, youth, flirting, female protagonist, identical twins ...
Time: 21st century, contemporary
Place: japan, asia
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: buddy comedy, not serious, humorous, witty, realistic ...
Audience: girls' night, date night
Plot: cross dressing, gender bending, advertising agency, hotel, workplace romance, showbiz, friendship, physical appearance, mistaken identity, couples, hidden identity, battle of the sexes ...
Time: 20th century, 90s, 80s
Place: usa, new york
Is relevant ?
 7.6
 258K
Mulan (1998)
Genre: Animation, Adventure, Family, Fantasy, Musical, War
Country: USA, China
Duration: 88 min.
Story: A tomboyish girl disguises herself as a young man so she can fight with the Imperial Chinese Army against the invading Huns. With help from wise-cracking dragon Mushu, Mulan just might save her country -- and win the heart of handsome Captain Li ...
Style: feel good, touching, captivating, light, humorous ...
Audience: kids, family outing, preschoolers, girls' night, chick flick
Plot: female protagonist, female warrior, princess, adventure, dragon, cross dressing, friendship, good versus evil, human spirit, woman dressed as man, hidden identity, escapades ...
Time: ancient history, 5th century
Place: ancient china, china, asia
Is relevant ?
You Are Beautiful (2009)
Genre: Comedy, Drama, Music, Romance
Country: South Korea
Duration: 60 min.
TV show
Story: You're Beautiful is a 2009 South Korean romantic comedy television drama series, starring Park Shin-hye, Jang Keun-suk, Lee Hong-ki of F.T. Island and Jung Yong-hwa of CN Blue. It is about a fictional boy band A.N.Jell and the relationship ...
Style: sentimental, humorous, semi serious, realistic
Audience: teens, girls' night
Plot: cross dressing, fall in love, gender bending, love and romance, music band, friendship, friends, rising to stardom, disorder, artists and showbiz, singing, love triangle ...
Time: 21st century, contemporary
Place: korea
Is relevant ?
 6.7
 24K
Albert Nobbs (2011)
Genre: Drama, Romance
Country: UK, Ireland, France, USA
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: stylized, sincere, touching, emotional, atmospheric ...
Plot: cross dressing, gender, maid, lesbian, master and servant, hotel, hidden identity, woman dressed as man, gender bending, society, transvestism, butler ...
Time: 19th century, 1890s, victorian era, 1800s, 1930s
Place: ireland, europe, england
Is relevant ?
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: feel good, romantic, humorous, touching, inspirational
Plot: cross dressing, gender disguise, tomboy, friendship, coffee shop, love triangle, love and romance, class differences, sister sister relationship, romance, hidden identity, korean ...
Place: korea
Is relevant ?
Related movie lists
Mulan: Rise of a Warrior (2009)
Genre: Adventure, Drama, Romance, War
Country: China, USA
Duration: 114 min.
Story: When barbarian hordes threaten her homeland, the brave and cunning Mulan disguises herself as a male soldier to swell the ranks in her aging father's stead. The warrior's remarkable courage drives her through powerful battle scenes and ...
Style: serious, exciting, stylized, epic, realistic
Plot: female warrior, cross dressing, tough girl, military life, female fighter, heroic mission, military, adventure, escapades, gender, soldier, heroes ...
Time: ancient history
Place: ancient china, china, asia
Is relevant ?
Big Momma's House (2000)
Genre: Action, Comedy, Crime
Country: Germany, USA
Duration: 99 min.
Story: When a street-smart FBI agent is sent to Georgia to protect a beautiful single mother and her son from an escaped convict, he is forced to impersonate a crass Southern granny known as Big Momma in order to remain incognito.
Style: funny, humorous, not serious, toilet humor, ridiculous ...
Audience: teens, family outing, girls' night
Plot: cross dressing, working undercover, disguise, undercover, physical appearance, crime, disorder, hidden identity, fbi, gender bending, fall in love, farce ...
Time: 20th century, 90s
Place: usa, georgia, southern usa
Is relevant ?
My Life in Pink (1997)
Genre: Drama
Country: Belgium, France, UK
Duration: 88 min.
Story: Ludovic is a small boy who cross-dresses and generally acts like a girl, talks of marrying his neighbor's son and can not understand why everyone is so surprised about it. His actions lead to problems for him and his family.
Style: touching, realistic, semi serious, offbeat, sentimental ...
Audience: date night
Plot: cross dressing, family relations, gender, coming of age, gender identity, transsexual, suburbs, gender bending, gay, self discovery, introspection, against the rules ...
Time: 90s
Place: belgium, paris france, france, europe
Is relevant ?
Shakespeare in Love (1998)
Genre: Comedy, Drama, History, Romance
Country: USA, UK
Duration: 123 min.
Story: Young Shakespeare is forced to stage his latest comedy, "Romeo and Ethel, the Pirate's Daughter," before it's even written. When a lovely noblewoman auditions for a role, they fall into forbidden love -- and his play finds a new ...
Style: stylized, romantic, sweet, inspirational, witty ...
Audience: girls' night, date night, chick flick
Plot: cross dressing, forbidden love, theater, writer's life, shakespeare, verbal byplay, hidden identity, unlikely couple, love and romance, lovers, theatre play, gender ...
Time: 16th century, 1930s
Place: england, europe, london
Is relevant ?
For You in Full Blossom (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, emotional, inspirational, humorous, talky
Plot: cross dressing, dormitory, friendship, boys' school, private school, rivalry, love, high school, everyday life, frustration, athlete's life, male friendship ...
Place: japan
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: feel good, humorous, semi serious, road movie, entertaining ...
Audience: girls' night
Plot: transvestism, cross dressing, gender bending, gay, friendship, gay slur, small town, on the road, culture clash, gender, cross country, showbiz ...
Time: 20th century, 90s
Place: nebraska, usa, new york, california, london ...
Is relevant ?
Related movie lists
Sungkyunkwan Scandal (2010)
Genre: Comedy, Drama, History, Romance
Country: South Korea
Duration: 70 min.
TV show
Story: Sungkyunkwan Scandal is a 2010 South Korean fusion historical drama about a girl who disguises herself as a boy while attending Sungkyunkwan, the Joseon Dynasty's highest educational institute, where no women were allowed. Directed by Kim ...
Style: romantic, touching, exciting, humorous, inspirational
Plot: gender disguise, cross dressing, romance, love triangle, student, friendship, female protagonist, king, rivalry, joseon dynasty, sword fight, social differences ...
Time: middle ages
Place: korea
Is relevant ?
 5.8
 21K
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: humorous, sexy, talky, light, romantic ...
Audience: teens, date night, girls' night, chick flick
Plot: teen sex comedy, cross dressing, elevator, man disguised as a woman, college, fall in love, youth, love and romance, college life, obsession, battle of the sexes, romance ...
Time: 90s
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: humorous, feel good, light, witty, colourful ...
Audience: date night, girls' night
Plot: comedy of errors, cross dressing, mistaken identity, twins, disguise, romance, gender bending, sea disaster, love, fall in love, couples, presumed dead ...
Time: 19th century, victorian era, victorian, 1890s, 1800s ...
Place: cornwall, england, london
Is relevant ?
Nuns on the Run (1990)
Genre: Comedy, Crime
Country: UK
Duration: 89 min.
Story: Brian and Charlie work for a gangster. When the boss learns they want to "leave" he sets them up to be killed, after they help rob the local Triads of their drug dealing profits. B&C decide to steal the money for themselves, but ...
Style: feel good, funny, humorous, entertaining, not serious ...
Audience: girls' night, teens
Plot: cross dressing, on the run, farce, fish out of water, misfit, nun, chase, convent, gender bending, priest, hidden identity, dishonesty ...
Time: 80s, 20th century
Place: london, europe, england
Is relevant ?
Big Momma's House 2 (2006)
Genre: Comedy, Crime
Country: USA
Duration: 99 min.
Story: FBI agent Malcolm Turner goes back undercover as Big Momma, a slick-talking, slam-dunking Southern granny with attitude to spare! Now this granny must play nanny to three dysfunctional upper class kids in order to spy on their computer hacked dad.
Style: humorous, feel good, entertaining, not serious, realistic ...
Audience: teens, girls' night
Plot: nanny, cross dressing, undercover, hidden identity, hacker, fbi, computer virus, special agents, working undercover, undercover agent, impersonation, disguise ...
Time: contemporary, 21st century
Place: california, los angeles, usa
Is relevant ?
Related movie lists
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, humorous, semi serious, fairy tale, funny ...
Audience: girls' night
Plot: cinderella story, fashion, cross dressing, hidden identity, family relations, fashion designer, parents and children, family problems, rivalry, workplace situations, family business, father daughter relationship ...
Time: 21st century, contemporary
Place: new york, usa, montreal, montreal quebec
Is relevant ?
Victor Victoria (1982)
Genre: Comedy, Music, Romance
Country: UK, USA
Duration: 134 min.
Story: A struggling female soprano finds work playing a male female impersonator, but it complicates her personal life.
Style: sexy, witty, clever, humorous, stylized ...
Audience: date night, girls' night
Plot: gender bending, cross dressing, cabaret, nightclub, woman dressed as man, music, jazz, romance, transvestite, chorus girl, showbiz, nightlife ...
Time: 1930s, 30s, 20th century, year 1934
Place: paris france, france, europe, chicago illinois
Is relevant ?
Tipping the Velvet (2002)
Genre: Drama, Romance
Country: UK
Duration: 177 min.
TV show
Story: Set in the 1890s, Tipping the Velvet tells the lesbian love affair between male impersonator music hall star Kitty Butler and Nan Astley.
Style: touching, stylized, serious, realistic, sexy ...
Audience: girls' night
Plot: lesbian, lesbian love, lesbian romance, sexual relations, lesbian interest, cross dressing, performer's life, gays and lesbians, fall in love, lesbianism, lesbian relationship, love and romance ...
Time: 19th century, victorian era, victorian, victorian england, 1890s
Place: england, europe, london
Is relevant ?
 5.5
 9K
Ladybugs (1992)
Genre: Comedy, Sport
Country: USA
Duration: 90 min.
Story: To climb the corporate ladder to success, a guy agrees to coach the company's all girl soccer team with the help of his secret weapon: his fiancee's son.
Style: humorous, feel good, realistic, not serious, offbeat ...
Audience: family outing, girls' night, teens, kids
Plot: cross dressing, soccer, underdog, sport team, sport, family, farce, gender, romance, rivalry, ambition, gender bending ...
Time: 20th century, 90s, 80s
Place: usa
Is relevant ?
 6.7
 8K
Pope Joan (2009)
Genre: Drama, History, Romance
Country: Germany, UK, Italy, Spain
Duration: 149 min.
Story: A 9th century woman of English extraction born in the German city of Ingelheim disguises herself as a man and rises through the Vatican ranks.
Style: captivating, realistic, serious
Plot: impossible love, cross dressing, vatican, ambition, clergy, woman dressed as man, healing power, monk, monastery, rise to the top, hidden identity, idealism ...
Time: middle ages, 9th century
Place: germany, rome italy, italy, europe
Is relevant ?
Connie and Carla (2004)
Genre: Comedy, Crime, Music
Country: USA
Duration: 108 min.
Story: After accidentally witnessing a mafia hit in the Windy City, gal pals Connie and Carla skip town for L.A., where they go way undercover as singers working the city's dinner theater circuit ... as drag queens. Now, it's not enough that they ...
Style: feel good, humorous, entertaining, funny, realistic ...
Audience: girls' night, teens, chick flick
Plot: cross dressing, performer's life, lifestyle, hidden identity, overnight success, romance, gender bending, best friends, dishonesty, comedy of errors, disorder, wrong place wrong time ...
Time: 21st century, contemporary
Place: los angeles, usa, chicago illinois, san francisco
Is relevant ?
Victor/Victoria (1995)
Genre: Comedy, Musical
Country: Japan, USA
Duration: 146 min.
Story: An out-of-work singer, Victoria Grant (Julie Andrews), meets a just-fired, flamboyant gay man in a diner in 1920's Paris. He convinces her to pretend to be a man who is a female impersonator in order to get a job. The act is a hit in a local ...
Style: stylized, humorous, feel good, semi serious, realistic ...
Audience: girls' night, date night
Plot: cross dressing, nightclub, jazz, based on movie, singer, transvestism, love and romance, dishonesty, romance, lifestyle, hidden identity, performer's life ...
Time: 1920s, 20th century, 20s
Place: paris france, france, europe, new york
Is relevant ?
Related movie lists