
- Tiffany Abreu (b. 29/10/1984), Brazilian volleyball player.
- Courtney Act (né Shane Gilberto Jenek, b. 18/2/1982), Australian drag queen.
- Calpernia Sarah Addams (né Scott Addams, b. 20/2/1971), actress, author, autobiographer, entrepreneur, activist, fiddle player
- Daniielle Alexis (né Shayne, b. 1987), Australian actor.
- Janice Allen (né John E. Allen, Jr.), American motion picture preservationist.
- Paul J. Allen, gay porn star
- Nádia Conceição Almada (né Jorge Leodoro, b. 28/1/1977), Portuguese-born Big Brother UK 2004 winner.
- Evie Amati (né Karl Booth Amati, b. 1/5/1992), Sydney axe attacker.
- Adèle Anderson, cabaret singer, actress, member of Fascinating Aida
- Enza "Supermodel" Anderson, drag performer
- Anohni (né Antony Paul Hegarty, b. 24/10/1971), English singer-songwriter.
- Arcipello, a British digital artist
- Regina Kaye Arthurell (né Reginald Kenneth Arthurell, b. c.1946), Australian serial killer
- Brianna Nicole Austin, writer and gender columnist.
- Mianne Bagger (né Michael Bagger, b. 25/12/1966), Danish-born Australian golfer.
- Dana Baitz, musician (pianist, producer, songwriter)
- Shirley Temple Bar, drag performer
- Jennifer Beck (aka The Flying Witch), Queensland pilot.
- Georgina Beyer (né George Bertrand, b. 11/1957), New Zealand's (and the world's) first transsexual mayor (1995) and member of parliament (2002)
- Joan Jett Blakk, drag performer
- Leyna Bloom, model.
- Sister Boom-Boom, drag queen
- Phinn Borg, transman.
- Kate Bornstein (né Albert Herman Bornstein, b. 15/3/1948), American author, playwright, performance artist and gender theorist
- Anya Bradford (né Nicolas Bradford, b. c. 1995)
- Sara Davis Buechner (né David Buechner, b. 8/9/1959), concert pianist
- Rachel Queen Burton, Australian TikToker
- Charles Busch, drag performer
- Meryn Cadell, Transman writer and singer-songwriter
- Patrick Califia (née Patricia Califia, b. 8/3/1954), Transman writer
- Endry Cardeño, Colombian transsexual actor
- Wendy Carlos (né Walter John Carlos, b. 14/11/1939), American composer and electronic musician.
- Carlotta (aka Carol Spencer) (né Richard Lawrence Byron, b. 2/9/1943), Australian showgirl and founder of Les Girls cabaret.
- Carmen Carrera (aka Carmen Roman) (né Christopher Ramon, b. 13/4/1985), American model.
- Christine Weston Chandler (aka Chris Chan) (né Christopher Weston Chandler, b. 24/2/1982), American internet personality, artist, and social media influencer. Arrested for incest.
- Parinaya Charoemphol (aka Nong Toom) (b. 9/6/1981), Thai actress and former kickboxer.
- Dorothy Ciner (né Robert Alan Durst, b. 12/4/1943), American cross-dressing serial killer.
- Stephanie Elizabeth Clark (né Ben Richard Clark), Sydney granddad killer.
- Bridget Clinch (né Matthew Clinch), Australian Veterans Party candidate.
- Roberta Close (né Luíz Roberto Gambine Moreira), Brasilian model.
- Nina Cohen (né Eric Louis Cohen, b. 5/5/1991), Californian activist.
- Megan Collier (aka Niki Renoir), Associate of Bevan von Einem.
- Lynn Anne Conway (né Robert Sanders, b. 2/1/1938), American computer scientist, electrical engineer and transgender advocate
- Caroline Cossey (aka Tula) (né Barry Kenneth Cossey, b. 31/8/1954), British model, author, and Bond girl
- Ricki Coughlan, Australian runner.
- Jayne County (aka Jayne Rogers) (né Wayne Vernoy Rogers, b. 13/7/1947), punk rock singer
- Jennifer Cross (né Carl J Cross), Australian-American computer programmer from Perth.
- Graham Dean (née Deanna Graham), UK gamer from Bedford
- Martine Delaney (né Martin Delaney, b. 15/10/1957), Tasmanian soccer player.
- Paula Denyer (né Paul Charles Denyer, b. 14/4/1972), Frankston serial killer.
- Dreuxilla Divine, drag queen
- Colin Kennedy Donovan, genderqueer/trans disability writer and anti-racist activist
- Julia Doulman (né Paul Doulman, b. 1963), Sydney bus driver.
- Aaron H. Dover, writer and educator
- Qwo-Li Driskill, writer, activist, and educator
- Michelle Dumaresq (né Michael Brandon Dumaresq, b. 15/6/1970), Canadian mountain bicyclist.
- Monet Dupree, drag performer
- Amanda Jane Dusting, Sydney archaeologist
- Siobhan Ellis (b. 1963), IT expert.
- Julian Eltinge, drag performer
- Jaime Elturk (aka Jaime Bone), drag computer manager
- Kataluna Enriquez (b. 26/4/1995), Miss Nevada 2021.
- Paul Erik (née Paula Erik), Canadian musician
- Jackie Enx (né Liam Joseph Jason, b. 13/4/1956), drummer for the heavy metal band Rhino Bucket
- Bulent Ersoy, Turkish transsexual singer
- Devi Ever (né Timothy Nathan Shortnacy, b. 1/1980), gamer and artist.
- Saoirse Ewart
- Brigitte Fell
- Jamie Faye Fenton (né Jay Fenton, b. 25/4/1954), computer game designer
- Bibiana Fernández, Spanish transsexual actress, model, performer
- Harvey Fierstein, drag performer, Hairspray
- Connie Fleming (aka Connie Girl), Jamaican-born American model.
- Tamara Von Forslun (né William Forslun), Australian witch, associated with the cult of COWA.
- Fallon Fox (né Boyd Burton, b. 29/11/1975), American mixed martial artist.
- Sienna Fox (aka CJ) (né Clayton James Palmer), Perth sex worker.
- Jacqualine Elizabeth Gaynor, female illusionist, show promoter
- Laura Jane Grace (né Thomas James Gabel, b. 8/11/1980), American musician, lead singer of Against Me!
- James Green, transman, writer & educator
- Stasha Goliaszewski, corporate activist, minister, radio host & producer TransPhillyRadio
- Jenni Gorman, transsexual parole officer from Lismore, Australia
- Rachael Goss a computer programmer and founder of TACT (Transgender Activists of Central Texas) and political activist
- Rachel Grant (né Richard Grant), West Australian goat farmer, involved in the failed WATSUP group.
- Karen Gurney, Australian Woman Network co-convenor.
- Maddison Hall (né Noel Crompton Hall, b. 4/12/1963), NSW hitchhiker murderer.
- Lauren Charlotte Harries (né James Charles Harries, b. 6/3/1978), British child prodigy and antiques collector.
- David Harrison, performer
- Harisu, transsexual model, singer and actress
- Rachel Ann Heath (né Richard Albert Heath), Australian psychologist.
- Mike Hernandez, writer and activist
- Jenny Hiloudaki (né Ioannis Hiloudaki, b. 21/2/1968), Greek model and brothel madam.
- April Holcombe, Australian activist.
- Clover Honey, drag queen
- Jill Hooley (né Jesse Hooley), Sydney transvestite university tutor.
- Mary Ann Horton (né Mark R. Horton, b. 21/11/1955), American Usenet and Internet pioneer.
- House of Diabolique, drag queen
- Laurel Hubbard (né Gavin Hubbard, b. 9/2/1978), New Zealand weightlifter.
- Stefanie Imbruglia (né Stephen Imbruglia), Australian sibling of Natalie Imbruglia.
- Dana International (aka Sharon Cohen) (né Yaron Cohen, b. 2/2/1969), Israeli pop singer
- Veronica Ivy (aka Rachel Veronica McKinnon) (né Rhys Raemond McKinnon, b. 18/7/1982), Canadian cyclist and academic.
- Eddie Izzard (Edward John Izzard, b. 7/2/1962), comedian who cross-dresses and calls himself an "executive transvestite"
- Andrea Jean James (b. 16/1/1967), American transwoman, entrepreneur, film producer, screenwriter, actress, and activist
- Caitlyn Jenner (né William Bruce Jenner, b. 28/10/1949), American Olympic decathlete and political candidate
- Michelle Josef (né Bodhan Hluszko, b. 1954), Canadian musician
- Kamikawa Aya, or Aya KAMIKAWA Tokyo municipal official (first transgendered person to seek elected office in Japan)
- Frances Margan Keeling, Sydney museum volunteer
- Mara Keisling (b. 29/9/1959), Founder of the National Center for Transgender Equality, passing several laws protecting transgender people.
- Dawn Marie Kereluik (b. 20/5/1955), Legally married in a Same-Sex Marriage to Katheryn Kereluik (née Katheryn Neudecker).
- Taff al-Khalifa, transman, member of Bahrain's royal family, now exiled
- Theresa Knott (né Terry Knott), London teacher
- Andreas Krieger (née Heidi Krieger, b. 20/7/1966), German transman shot putter.
- Dani Laidley (né Dean James Laidley, b. 27/3/1967), Former Australian Rules footballer and coach.
- Mado Lamotte, drag performer
- Jennifer Jane Leitham (né John Leitham, b. 10/8/1953), transsexual jazz bassist
- Amanda Lepore (né Armand Lepore, b. 21/11/1967), American model and performance artist.
- Hedda Lettuce, drag performer
- Rachel Levine (né Richard Leland Levine, b. 28/10/1957), American pediatrician
- Miss Shangay Lily, drag performer
- Shirley Q Liquor, drag queen
- Charles Ludlam
- Lypsinka (né John Epperson, b. 24/4/1955), drag queen
- Stephanie McCarthy, Australian musician, lead singer of Love Maul.
- Deirdre McCloskey (né Donald Nansen McCloskey, b. 11/9/1942), noted American Economist, argued The McCloskey critique
- Catherine McGregor (aka Cate McGregor) (né Malcolm Gerard McGregor, b. 24/5/1956), Australian commentator
- Kellie Maloney (né Francis Thomas Maloney, b. 23/1/1953), English boxing manager.
- Christine Mancini, drag performer
- Roslyn L. Manley, transsexual advocate/activist. First openly out transsexual to hold elected office in the United States. Elected June 2004 to Democratic Central Committee in California.
- Chelsea Elizabeth Manning (né Bradley Edward Manning, b. 17/12/1987), former American soldier and activist.
- Brini Maxwell, drag performer
- Tiesa Meri Meskis (aka Jade Gillies) (né Nathan Phillip Kennedy, b. 28/10/1975), Aberdeen city councillor.
- Shannon Minter, transman, attorney, legal director of National Center for Lesbian Rights
- Agnes Moore (aka Miss Peppermint) (né Kevin Moore b. 31/1/1980), American actress and singer.
- Dana Moran, NASCAR driver 1970, sprint car champion, super modified champion, advocate
- Billy More, drag queen
- Hannah Olivia Mouncey (né Callum Philip Charles Mouncey, b. 21/10/1989), Australian Rules footballer and Olympic handballer.
- Andrea Lane Mun (aka Oxsi Nekro) (né Jacob Andrew Camello), Oregon trans activist.
- Nancy Reynolds Nangeroni (né John Arthur Nangeroni, b. 30/9/1953), trans activist, GenderTalk Radio founder/producer/host, writer, musician, engineer
- Norrie (aka Norrie May Welby) (né Bruce Norrie Watson, b. 23/5/1961), Scottish-born convicted fraudster.
- Terri O'Connell, stock car racer, previously paricipated in NASCAR under the name J.T. Hayes
- Kathleen Padilla, the first openly transgender official in Pennsylvania, Democratic delegate to the 2004 Democratic Presidential Convention in Boston, Commissioner Philadelphia Police Advisory Commission
- Rachael Padman (né Russell Padman, b. 1954), Australian physicist.
- Dee Palmer (né David Victor Palmer, b. 2/7/1937), English musician.
- Larry Paciotti, porn movie director, transvestite
- Elliot Page (née Ellen Grace Philpott-Page, b. 21/2/1987), Canadian transman actor.
- Jaime Page (né Jamie Page), Australian guitarist.
- Pauline Pantsdown (né Simon Hunt), Australian drag queen
- Nicole Louise Pearce (né Paul Wayne Luckman, b. 1/11/1964), Melbourne child murderer.
- Jamie Delphine Penn (né Jeremy Penn), American socialist candidate.
- Grayson Perry, artist whose work sometimes features his female alter ego, Claire. Winner of the 2003 Turner Prize for art
- Kim Petras (né Timothy Petras, b. 27/8/1992), German singer and singwriter.
- Dana Pham, Sydney university activist.
- Charles Pierce, drag performer
- Angela Piland (b. 17/4/1981), model
- Lee-Anne Purcell, Perth transvestite sex worker, and celebrity stalker
- Quinn (née Rebecca Catherine Quinn, b. 11/8/1995), non-binary Canadian footballer.
- Mark Rees, activist
- Madame Regina, transgender author
- Rebecca Ann Richards (né Richard Windsor), Sydney security consultant and shooter
- Renée Richards (né Richard Henry Raskind, b. 19/8/1934), professional tennis player
- Jennifer Diane Reitz (b. 30/12/1959), computer programmer, cartoonist and gender rights advocate
- Joan Elizabeth Roughgarden (né Jonathan David Roughgarden, b. 13/3/1946), professor of biology; evolution and ecology expert
- RuPaul (RuPaul Andre Charles, b. 17/11/1960), American drag queen
- Cindy Ryan, Perth sex worker, involved in the failed WATSUP group
- Chrisentiae Saint-Piaf, Melbourne acitivist.
- Fulvia Celica Siguas Sandoval, the person with the most Gender Reassignment Surgeries in the world and perhaps the first transsexual in Peru
- José Sarria, drag performer, first LGBT person to run for elective office in the USA, activist, noted fund raiser for AIDS services
- Lily Savage (né Paul James O'Grady, b. 14/6/1955), drag performer
- Erik Schinegger, 1968 women's world champion downhill skier for Austria
- Scott Turner Schofield, writer, performer
- Laura Anne Seabrook (né Larry Dunning, b. 1957), Australian artist.
- Mokgadi Caster Semenya (b. 7/1/1991), South African 800m and 400m runner.
- Melissa Sklarz (né Richard Sklarz, b. 2/1951), the first openly transgender public official in New York State, Democratic county judicial delegate in Manhattan.
- Olivia Sindel (né Oliver Mark Sindel, b. c. 1996).
- Thalia Sinden (aka Shanika) (né Derek Lulu Sinden, b. 23/11/1969), Brisbane granny killer.
- Georgie Stone (né George Robertson Stone, b. 20/5/2000), Australian actor.
- Sandy Stone (né Zelig Ben-Natan), transgender activist and author
- Ethan St. Pierre, transsexual man, hate crimes survivor, radio host transfm.org
- Sharon Stolzenberg (aka Sharon Brown), former Gender Centre treasurer and nurse.
- Margaret Stumpp, transsexual co-manager of Quantitative Management department at Prudential Financial Inc.
- Jolene Sugarbaker, drag queen
- Tina Dee Taylor, transgendered actor, artist and writer in Hollywood
- Terre Thaemlitz (aka DJ Sprinkles) (b. 1968), American musician.
- Christine Tham (né Chris Tham, b. 8/8/1964), Malaysian-born Australian wealth manager.
- Lia Thomas (né Will Thomas, b. 1999), Pennsylvania swimmer.
- Nicole Thomas, scientist
- Stephen Thorne, transman, police officer
- Pussy Tourette (né Mark Cliser), drag performer and singer
- Miss Understood (né Alexander Heimberg), NY drag performer and entrepreneur
- Pieter Dirk Uys, drag performer
- Daniel Van Oosterwijck, transman, lawyer
- Max Valerio, performer
- Kelly van der Veer (né Ferry van der Veer, b. 6/5/1980), Big Brother Holland contestant.
- Del Lagrace Volcano, transman, performer and photographer
- Lana Wachowski (né Laurence Wachowski, b. 21/6/1965), American film director and producer.
- Lily Wachowski (né Andrew Paul Wachowski, b. 29/12/1967), American film director and producer.
- Valerie Wagstaff, NSW police officer.
- Rachael Wallbank (né Richard Dennis Wallbank, b. 4/3/1956), Sydney lawyer
- Kerry Warburton, Associate of Bevan von Einem.
- Megan Lee Webb (né Lee Webb), Queensland-born Sydney cyclist and itinerant
- Michelle Websdale (né Geoffrey Ian Websdale, b. c. 1969), Griifith serial killer.
- Stephen Whittle, transman, lawyer, writer and educator
- Taragh Wilde, University student activist.
- Chelsea Andrea Wolfe (b. 5/5/1993), American BMX freestyle rider.
- Carol Wood, Australian artist.
- Tara Wood-Bradley (né Paul A. Wood-Bradley), Cessnock physiotherapist.
- Conchita Wurst (né Thomas Neuwirth, b. 6/11/1988), Austrian drag performer.
- Jin Xing, transsexual Chinese dancer
- Jessica Yaniv (aka Jessica Simpson) (né Jonathan Gill Yaniv, b. 12/6/1987), Canadian activist.
- Miranda Jane Yardley (né Peter J. Yardley, b. 11/1967), English rugby player and publisher.
- Philippa York (né Robert Charles Millar, b. 13/9/1958), Scottish professional road racing cyclist.
- Megan Youngren (b. 1991), American marathon runner.
- Lilith Medea Zaharias (né Jonathan Zaharias), Australian Greens candidate.
20th and 21st century individuals
- Gwen Amber Rose Araujo (né Edward Araujo, Jr., 24/2/1985 - 4/10/2002), American Latina pre-operative transsexual.
- April Ashley (né George Jamieson, 29/4/1935 - 27/12/2021), British model and celebrity. Scandalous autobiography withdrawn due to plagiarism.
- Adele Evelyn Bailey (né Paul David Bailey, 1955 - 12/9/1978), New Zealand-born Sydney sex worker.
- Veronica Maree Baxter (aka Telisha Drury) (né James Llewellyn Drury, 23/2/1975 - 16/3/2009), Sydney sex worker. Arrested for drug trafficking, suicided while being assessed at the Metropolitan Remand and Reception Centre in Silverwater.
- Danielle Bunten Berry (aka Dani Berry) (né Daniel Paul Bunten, 19/2/1949 - 3/7/1998), U.S. software developer, author of several titles for Electronic Artsin the 1980s, died of cancer.
- Mhelody Polan Bruno (1994 - 22/9/2019), Pinnoy call centre worker.
- Linn Dorothy Bullock (né Kevin O'Brien), New Zealand nurse.
- Coccinelle (aka Jacqueline Charlotte Dufresnoy) (né Jacques Charles Dufresnoy, 23/8/1931 - 9/10/2006), French entertainer and celebrity.
- Katherine Fiona Cummings (né John Lawrence Cummings, 28/3/1935 - 26/1/2022), Australian author and former Polare editor
- Jackie Curtis (né John Curtis Holder Jr., 19/2/1947 - 15/5/1985), U.S. drag queen who had a friendship with the famous pop artist, Andy Warhol
- Candy Darling (né James Lawrence Slattery, 24/11/1944 - 21/3/1974), part of Andy Warhol's Factory.
- Divine (né Harris Glenn Milstead, 19/10/1945 - 7/3/1988), actor and drag performer
- Ethyl Eichelberger (né James Roy Eichelberger, 17/7/1945 - 12/8/1990) drag performer, actor, performance artist.
- Lili Elbe (aka Lili Ilse Elvenes) (né Einar Magnus Andreas Wegener, 28/12/1882 - 13/9/1931), Danish transsexual, one of the first women to undergo a crude form of sexual reassignment surgery, through five operations which were completed by 1930. Fifteen months after her final surgery, she either died from complications or faked her own death to avoid the media attention.
- Stig Engström (Stig Folke Wilhelm Engström, 26/2/1934 - 26/6/2000), Swedish suspect in the assassination of prime minister Olof Palme. Dressed androgynously and described themselves as non-binary.
- Bella Evangelista, also known as Elvys Perez (1978 - 16/8/2003), Latina drag performer
- Eugene Falleni (aka Harry Leo Crawford) (née Eugenia 'Nina' Falleni, 25/7/1875 - 10/6/1938), Italian-born Australian transman convicted of murder.
- Diane Leslie Feinberg (1/9/1949 - 15/11/2014), activist and author.
- Prudence Charmaine Firman (né Gregory Francis Acton, 5/5/1955 - 10/10/2008), Associate of Bevan von Einem.
- Julia Grant (né George Roberts, 21/9/1954 - 2/1/2019), first transgender person to have their transition documented on television. Grant later regretted surgery and warned others not go ahead with the procedure.
- Aidy Griffin (né Aidan Griffin, 28/7/1954 - 7/10/2021), Sydney transvestite taxi driver. Died from emphysema with lung cancer.
- Marjorie Harwood (né Martin Luke Harwood, 8/12/1979 - 1/7/2018).
- Tyra Hunter (né Tyrone Michael Hunter, 1970 - 7/8/1995), U.S. transsexual woman.
- Rose Jackson (né Barry Charles Jackson, 1934 - 21/7/2011), Sydney entertainer and costumier.
- Marsha P. Johnson (né Malcolm Michaels Jr., 24/8/1945 - 6/7/1992), transgender activist, involved in Stonewall (UK), co-founder of Street Transvestite Action Revolutionaries (STAR).
- Frankie 'Halfpint' Jaxon (né Frank Devera Jackson, 3/2/1895 - 15/5/1953), American singer and entertainer who has often sung with a female voice
- Christine Jorgensen (né George William Jorgensen, Jr., 30/5/1926 - 3/5/1989), one of the first Americans to have sexual reassignment surgery in 1952
- Pepper LaBeija (né William Jackson, 5/11/1948 - 14/5/2003), Harlem, New York drag queen, subject of the documentary Paris Is Burning
- Vanessa Lane (né Barry Wayne Venables, 7/8/1955 - 15/10/1997), Lover of Snowtown serial killer Robert Joe Wagner.
- Danny La Rue (né Daniel Patrick Carroll, 26/7/1927 - 31/5/2009), British drag performer.
- April Lawton (né Gregory Ferrara, 30/7/1948 - 23/11/2006), American guitarist and artist.
- Joanne Lillecrapp (né John Douglas Lillecrapp, 28/2/1948 - 4/11/2001), Adelaide truck driver. Former suspect in the disappearance of Joanne Ratcliffe and Kirste Gordon.
- Cam Lyman (née Camilla Lowell Lyman, 4/9/1932 - 31/7/1987), millionaire transman, disappeared in 1987
- Amber McLaughlin (né Scott A. McLaughlin, 13/1/1973 - 3/1/2023), first transgender executed for murder in the UNited States.
- Kimberley McRae (aka Isabella Lawson) (1950 - 14/1/2020), Sydney sex worker and author.
- Angela Morley (né Walter Stott, 10/3/1924 - 14/1/2009), English composer and conductor.
- Jan Morris (né James Humphry Morris, 2/10/1926 - 20/11/2020), Welsh travel writer
- Sarah Leanne Novak (né Stephen Stanton, 20/4/1957 - 16/12/2014), Associate of Bevan von Einem.
- Roberta Perkins (né Robert A. Perkins, 30/4/1940 - 26/6/2018), Sydney sex worker from Adelaide. Died in a nursing home from complications related to dementia.
- Mayang Sari Prasetyo (né Febri Andriansyah, 13/2/1987 - 3/10/2014), Indonesian cabaret worker.
- Miriam Rivera (aka Victoria) (1/1981 - 5/2/2019), Mexican model and actor.
- Sylvia Rivera (né Ray Rivera, 2/7/1951 - 19/2/2002), transgender activist, resisted police at Stonewall on June 27, 1969
- Carmen Rupe (né Trevor David Rupe, 10/10/1936 - 14/12/2011), Sydney sex worker from New Zealand
- Craig Russell (né Russell Craig Eadie, 10/1/1948 - 30/10/1990), Canadian actor and female impersonator.
- Chloe Sagal (né John Paul Neumann, 3/1987 - 19/6/2018), American game developer.
- Nadine Candice Stransen (aka Lexy Gadney) (né Andrew Wangmann, 14/11/1953 - 4/2/2016), Sydney artist and vagrant. Died from an accidental fall while intoxicated in Woolloomooloo. Stransen had been in remission from leukaemia.
- Jeanette Schmid (aka Baroness Lips von Lipstrill) (né Rudolf Schmid, 6/11/1924 - 9/3/2005), Austrian whistler.
- Karen Leonie Taylor (aka Sharyn) (né Rodney Taylor, b. c.1972 - 5/4/2015), West Australian drag queen from Lesmurdie
- Leigh Varis-Beswick (né Harry Varis, 16/1/1949 - 21/3/2020), Kalgoorlie brothel madam.
- Ed Wood, Jr. (Edward Davis Wood Jr., 10/10/1924 - 10/12/1978), film-maker with transvestite tendencies
- Holly Woodlawn (né Haraldo Santiago Franceschi Rodriguez Danhakl, 26/10/1946 - 6/12/2015), U.S. drag queen, part of Andy Warhol's Factory.
- Sophie Xeon (né Samuel Long, 17/9/1986 - 30/1/2021), Glasgow-born music producer.
Earlier historical individuals
It is often difficult to construe the gender and sexual identity of pre-modern individuals. In many societies, those whom Western society might consider homosexual or bisexual are or were considered transgendered.
Many of these persons cross-dressed during wartime for various purposes.
- Herculine Barbin, 19th Century French hermaphrodite
- James Barry, female bodied surgeon who lived as a man throughout his/her life, according to some accounts in order to be able to practice medicine.
- Christina of Sweden, Queen of Sweden from 1632 to 1654 who went by the name of "Count Dohna" at one point, dressing in male attire as part of the role. Despite speculation, modern medical examinations of her remains have not uncovered any evidence of intersexuality, although such examinations might not be conclusive.
- Elagabalus, Roman Emperor
- Joan of Arc, martyr accused of cross-dressing and was forced to wear a dress during her imprisonment. Later tried and executed.
- Chevalier d'Eon, French diplomat (1728–1810) who claimed that he had been born a girl and later adopted a female persona.