Category:Men wearing female clothing

See also categories: Men wearing male clothing, Women wearing female clothing and Women wearing male clothing.

Subcategories

This category has the following 5 subcategories, out of 5 total.

B

Men wearing bikinis‎ (1 C)

F

Men wearing French maid outfits‎ (9 F)

H

Men wearing high-heeled shoes‎ (1 C, 30 F)

T

Men wearing tights‎ (68 F)

U

Men in female underwear‎ (7 C, 4 F)

Media in category "Men wearing female clothing"

The following 200 files are in this category, out of 338 total.

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"Ballet Dancers" from Sentinel, Shrewsbury.jpg 620 × 477; 50 KB
"This Is The Army," Irving Berlin's Broadway hit, with an all-soldier cast, is making $40,000 a week for Army Relief.... - NARA - 535774.tif 3,000 × 2,371; 6.78 MB
'That's what's the matter' (6189303633).jpg 617 × 1,000; 544 KB
(Boys baseball team dressed as sailor girls, San Francisco Mission High School) (14476868006).jpg 959 × 730; 85 KB
SolserHesse.jpg 275 × 450; 18 KB
Musette, Oscarsteatern 1908. Rollporträtt - SMV - GA014.tif 5,803 × 8,068; 89.32 MB
This-Is-The-Army gals (Broadway).jpg 2,904 × 2,292; 3.11 MB
1977 - Festival musica cinema teatro gay Parma.jpg 1,636 × 1,036; 776 KB
9551 - Presidio anticlericale, Milano, 2 June 2012 - Foto di Giovanni Dall'Orto.jpg 1,880 × 2,816; 2.18 MB
Royal Liberty Morris with 'molly' at Broadstairs Folk Week 2017, Kent, England 1.jpg 3,000 × 2,000; 4.24 MB
Royal Liberty Morris 'molly' (Pete) at 2017 Broadstairs Folk Week, Kent, England 6.jpg 1,500 × 3,000; 2.25 MB
Royal Liberty Morris 'molly' (Pete) at 2017 Broadstairs Folk Week, Kent, England 7.jpg 1,687 × 3,000; 2.81 MB
Royal Liberty Morris with 'molly' at Broadstairs Folk Week 2017, Kent, England 2.jpg 2,250 × 3,000; 4.08 MB
Royal Liberty Morris with 'molly' at Broadstairs Folk Week 2017, Kent, England 3.jpg 3,000 × 1,688; 3.42 MB
Royal Liberty Morris with 'molly' at Broadstairs Folk Week 2017, Kent, England 4.jpg 2,250 × 3,000; 4.04 MB
Royal Liberty Morris with 'molly' at Broadstairs Folk Week 2017, Kent, England 5.jpg 2,250 × 3,000; 4.2 MB
Royal Liberty Morris with 'molly' at Broadstairs Folk Week 2017, Kent, England 6.jpg 3,000 × 2,000; 3.08 MB
Royal Liberty Morris with 'molly' at Broadstairs Folk Week 2017, Kent, England 7.jpg 3,000 × 2,250; 3.94 MB
Royal Liberty Morris with 'molly' at Broadstairs Folk Week 2017, Kent, England 8.jpg 2,400 × 3,000; 3.95 MB
Royal Liberty Morris with 'molly' at Broadstairs Folk Week 2017, Kent, England 9.jpg 2,250 × 3,000; 3.66 MB
Royal Liberty Morris with 'molly' at Broadstairs Folk Week 2017, Kent, England 10.jpg 2,250 × 3,000; 3.7 MB
Royal Liberty Morris with 'molly' at Broadstairs Folk Week 2017, Kent, England 11.jpg 2,400 × 3,000; 3.42 MB
Royal Liberty Morris 'molly' (Pete) at 2017 Broadstairs Folk Week, Kent, England 1.jpg 2,400 × 3,000; 5.33 MB
Royal Liberty Morris 'molly' (Pete) at 2017 Broadstairs Folk Week, Kent, England 2.jpg 2,400 × 3,000; 5.19 MB
Royal Liberty Morris 'molly' (Pete) at 2017 Broadstairs Folk Week, Kent, England 3.jpg 3,000 × 2,000; 3.18 MB
Royal Liberty Morris 'molly' (Pete) at 2017 Broadstairs Folk Week, Kent, England 4.jpg 2,000 × 3,000; 3 MB
Royal Liberty Morris 'molly' (Pete) at 2017 Broadstairs Folk Week, Kent, England 5.jpg 2,000 × 3,000; 3.07 MB
3skirts (183829780).jpg 600 × 556; 125 KB
A cross dresser party in India.JPG 2,592 × 3,888; 4.44 MB
A man dancing during Ecuadorian folk celebration, dressed in traditionnal women clothing.jpg 2,812 × 2,109; 3.25 MB
A sissy cross dresser in feminine office wear.png 724 × 2,561; 3.19 MB
An Adventuress (1920) - 2.jpg 667 × 837; 109 KB
Albert Mol als vrouw verkleed in TV-programma A star is born, Bestanddeelnr 925-8440.jpg 2,451 × 3,684; 1.41 MB
Albert Mol als vrouw verkleed in TV-programma A star is born, Bestanddeelnr 925-8441.jpg 2,451 × 3,684; 1.4 MB
Albert Mol als vrouw verkleed in TV-programma A star is born, Bestanddeelnr 925-8442.jpg 2,451 × 3,684; 1.53 MB
An Egyptian dancer photographed by Wilhelm Hammerschmidt of Cairo.jpg 362 × 589; 66 KB
Anders de Wahl Charleys tant.jpg 2,388 × 3,215; 6.75 MB
Anders de Wahl, rollporträtt - SMV - H2 149.tif 2,646 × 4,005; 30.34 MB
Anime Expo 2011 (5917941474).jpg 1,200 × 1,600; 354 KB
Anti suffrage postcard- If we can't have the vote, we can wear the trousers.jpg 1,998 × 3,210; 1.66 MB
Artiste-transformiste.jpg 3,168 × 4,752; 2.5 MB
Axel Taube & Alex Peters (11447337055).jpg 650 × 1,024; 470 KB
Bajouca, Portugal (105447346).jpg 1,800 × 2,700; 2.58 MB
Bam Bam 2016 Got7.jpg 1,200 × 1,600; 133 KB
BDSM couple with spanking paddle.jpg 4,034 × 2,868; 10.47 MB
Boys (6895426164).jpg 2,500 × 1,912; 1.62 MB
Buddy D Dress Rehearsal and 'Stache Dash' 15.jpg 4,272 × 2,848; 2.46 MB
Bundesarchiv Bild 101I-103-0934-37, Nordeuropa, Truppenunterhaltung.jpg 518 × 800; 42 KB
Bundesarchiv Bild 101I-103-0934-38, Nordeuropa, Truppenunterhaltung.jpg 789 × 507; 43 KB
Can-can democrático, de Xaudaró, Gedeón, 02-09-1906.jpg 2,136 × 3,012; 2.44 MB
Caracerización.jpg 2,592 × 1,456; 1.27 MB
Carnaval1911(PçªPríncipeReal).jpg 2,048 × 1,453; 332 KB
CastelliPourceaugnac.jpg 1,709 × 2,204; 1.52 MB
CDBlack nightgown.jpg 2,112 × 2,816; 971 KB
CDNightgown.jpg 1,570 × 1,176; 1.05 MB
CDPetticoatGown.jpg 1,562 × 1,160; 974 KB
CDSeamedStockings.jpg 1,200 × 1,600; 1,011 KB
CDshiny stockings.jpg 2,030 × 2,724; 709 KB
Charles Bannister Polly Peachum.jpg 484 × 686; 147 KB
Chasing the Chaser.jpg 600 × 450; 37 KB
Clutch (6343148329).jpg 4,272 × 2,848; 8.27 MB
Coffee Run Cross Dresser by David Shankbone.jpg 2,011 × 1,990; 2.34 MB
ColognePride 2016, Parade-8168.jpg 1,648 × 3,339; 3.63 MB
Copenhagen Pride Parade 2014 07.jpg 2,560 × 1,920; 2.95 MB
Copenhagen Pride Parade 2016 07.jpg 1,920 × 2,560; 2.9 MB
Copenhagen Pride Parade 2017 21.jpg 1,920 × 2,560; 2.62 MB
Copenhagen Pride Parade 2017 29.jpg 2,560 × 1,920; 2.68 MB
Copenhagen Pride Parade 2019 18.jpg 1,920 × 2,560; 2.85 MB
Copenhagen Pride Parade 2023 41.jpg 1,297 × 1,730; 1.87 MB
Crossdresser Belle-Glamour SNV12328.JPG 506 × 900; 239 KB
Crossdresser in leather shirt and leather skirt.jpg 2,632 × 3,704; 1.33 MB
Crossdresser in leather skirt and leather jacket.jpg 1,536 × 2,048; 1.13 MB
Crossdresser in leather.jpg 1,536 × 2,048; 1.28 MB
Crossdresser-Belle Glamour IMG 0239.JPG 506 × 900; 86 KB
Crossdresser-Belle Glamour IMGP0434.JPG 506 × 900; 130 KB
Crossdresser-Belle Glamour IMGP0435.JPG 506 × 900; 127 KB
Crossdresser-Belle Glamour IMGP0453.JPG 507 × 900; 162 KB
Crossdresser-Belle Glamour IMGP0537.JPG 506 × 900; 135 KB
Crossdresser-Belle Glamour IMGP0568.JPG 506 × 900; 112 KB
Crossdresser-Belle Glamour IMGP2640.JPG 506 × 900; 164 KB
Crossdresser-Belle Glamour SNV14941.JPG 506 × 900; 158 KB
Crossdresser-Belle Glamour SNV14948.JPG 506 × 900; 153 KB
Crossdresser-Belle Glamour SNV14977.JPG 506 × 900; 144 KB
Crossdresser-nl.jpg 122 × 300; 7 KB
Crossdressing boy.jpg 768 × 1,024; 353 KB
Crossdressing circa 1890 Frances Benjamin Johnston (right).jpg 512 × 708; 67 KB
CSD 2006 Cologne 07.jpg 1,311 × 2,000; 924 KB
Dancer in front of a divan.jpg 1,890 × 3,000; 1.5 MB
Den politiske kandestøber 08.jpg 2,808 × 1,872; 3.77 MB
Denim jacket and leather pants.jpg 3,936 × 5,248; 9.23 MB
Devara jade.jpg 371 × 1,024; 85 KB
Drag queens on Zhonxiao E RD--Taiwan Pride 2005.jpg 1,664 × 2,496; 1.83 MB
Drinkwater Meadows; John Howard Payne; George John Bennett as the witches in 'Macbeth'.jpg 800 × 625; 191 KB
Eddie Valdez & Lars Jacob "Birds Think" Wild Side Story 1979.jpg 532 × 449; 30 KB
Edmund Fischer (11447335455).jpg 1,024 × 816; 531 KB
El excluido.jpg 457 × 480; 38 KB
Elis Ellis, rollporträtt - SMV - GE035.tif 5,826 × 7,956; 88.43 MB
Ella Guru, Sexton Ming with Face Pack.jpg 269 × 323; 27 KB
Eltinge11.jpg 193 × 310; 7 KB
Entertainment in the British Army on the Western Front, 1914-1918 Q8963.jpg 800 × 622; 65 KB
Ernst Fastbom, rollporträtt - SMV - H3 017.tif 1,917 × 3,982; 21.87 MB
F. Scott Fitzgerald circa 1915.jpg 570 × 794; 444 KB
Fabiola Hartjesdag 2007.jpg 680 × 920; 246 KB
Fabiola2007.jpg 800 × 1,066; 962 KB
Fancy dress aboard ship, Sir Charles Kingsford Smith dressed as girl (10299664605).jpg 623 × 1,024; 142 KB
Fanny (Frederick Park).jpg 400 × 453; 43 KB
Fantasy Fest 2012 in Key West Florida - 04.jpg 5,184 × 3,456; 6.1 MB
Femboy Maid Cosplay.jpg 2,398 × 3,056; 834 KB
Ferdinand Hörschelmann (11447386634).jpg 1,024 × 813; 560 KB
FirstSPIphoto.jpg 597 × 604; 69 KB
Flickr - Israel Defense Forces - Militant Disguised as Woman Attempts Shooting.jpg 1,177 × 1,391; 464 KB
Flickr - Israel Defense Forces - Terrorist Disguised as a Woman (1).jpg 1,176 × 1,750; 267 KB
Flickr - Israel Defense Forces - Terrorist Disguised as a Woman.jpg 1,766 × 1,191; 354 KB
Folkans dollarprinsessa, Folkteatern 1909. Rollporträtt - SMV - GF030.tif 5,783 × 7,920; 87.38 MB
Folkans dollarprinsessa, Folkteatern 1909. Rollporträtt - SMV - GF031.tif 5,807 × 7,980; 88.41 MB
Folkans dollarprinsessa, Folkteatern 1909. Rollporträtt - SMV - GF032.tif 5,807 × 7,956; 88.14 MB
Tableau, men, costume, fun, yard Fortepan 26317.jpg 4,497 × 3,702; 9.53 MB
Fouad Arbabi "Obvióla" Wild Side Story 2013.jpg 673 × 519; 39 KB
Frank Drew in a female role.jpg 590 × 952; 286 KB
Gay 'Senoritas' ballet of the minstrel show at the Capitol Theatre, Halifax, Nova Scotia, Canada, April 1931.jpg 3,254 × 2,581; 1.09 MB
Gay pride - Dog tag (14348446328).jpg 2,522 × 3,614; 4.15 MB
Gay Pride Madrid 2013 - 130706 185817.jpg 3,345 × 5,017; 4.49 MB
Gay Pride Madrid 2013 - 130706 201204.jpg 3,221 × 4,831; 4.75 MB
Gay Pride Madrid 2013 - 130706 202129.jpg 3,648 × 4,316; 5.58 MB
Gay Pride Madrid 2013 - 130706 202133.jpg 4,883 × 3,255; 5.49 MB
Gay Pride Madrid 2013 - 130706 203034.jpg 3,158 × 4,738; 6.08 MB
Gay Pride Madrid 2013 - 130706 203035.jpg 3,648 × 5,472; 6.29 MB
Gay Pride Madrid 2013 - 130706 210514.jpg 3,263 × 4,351; 4.92 MB
Gipsy tights.jpg 3,072 × 4,608; 3.44 MB
Gloeden, Wilhelm von (1856-1931) - n. 0923 recto - da - Amore e arte, p. 32.jpg 947 × 1,276; 502 KB
Gothic lolita clothing.jpg 2,912 × 4,368; 3.76 MB
Group of men standing on a grass field (AM 76706-1).jpg 1,275 × 955; 674 KB
Group portrait of six men standing on grass field (AM 76704-1).jpg 1,275 × 954; 717 KB
Group portrait of three men in costume (AM 76692-1).jpg 1,275 × 953; 627 KB
Group portrait of three men in costume (AM 76693-1).jpg 1,275 × 950; 618 KB
Group with man dressed in woman's clothing circa 1900 (archive ref DDX1319-4-EYC116) (25811767326).jpg 563 × 747; 74 KB
Handbuch der Sexualwissenschaften p.425.jpg 1,587 × 3,423; 9.51 MB
Happy Days Ron Howard Henry Winkler 1974.JPG 748 × 563; 101 KB
Harvard Theatre Collection - Neil Burgess TCS 1.4069.jpg 1,448 × 2,134; 618 KB
Harvard Theatre Collection - Neil Burgess TCS 1.4070.jpg 1,409 × 2,134; 734 KB
Harvard Theatre Collection - Neil Burgess TCS 1.4076.jpg 1,342 × 2,036; 547 KB
Harvard Theatre Collection - Neil Burgess TCS 1.4079.jpg 1,353 × 2,046; 499 KB
Harvard Theatre Collection - Washington Norton TCS 1.775.jpg 1,378 × 1,905; 474 KB
Heterosexual crossdresser.jpg 1,958 × 2,893; 1.01 MB
Hjalmar Hirsch, rollporträtt - SMV - H4 063.tif 1,993 × 3,896; 22.24 MB
HK TW 荃灣 Tsuen Wan 沙咀道 Sha Tsui Road Ham Tin Street 1647pm February 2022 Px3 07 易服者.jpg 4,000 × 3,000; 5.5 MB
HK TW 荃灣 Tsuen Wan 沙咀道 Sha Tsui Road Ham Tin Street 1647pm February 2022 Px3 08.jpg 4,000 × 3,000; 4.91 MB
HK TW 荃灣 Tsuen Wan 沙咀道 Sha Tsui Road Ham Tin Street 1647pm February 2022 Px3 09 Bank of China.jpg 4,000 × 3,000; 5.33 MB
HK TW 荃灣 Tsuen Wan 沙咀道 Sha Tsui Road Ham Tin Street shop 牛奶冰室 Milk Cafe by 亞洲國際餐飲集團 Taste of Asia Group February 2022 Px3 03.jpg 4,000 × 3,000; 4.18 MB
HK TW 荃灣 Tsuen Wan 沙咀道 Sha Tsui Road Ham Tin Street shop 牛奶冰室 Milk Cafe by 亞洲國際餐飲集團 Taste of Asia Group February 2022 Px3 06 易服者 lolita clothing.jpg 4,000 × 3,000; 4.21 MB
Hot Wig (5878924631).jpg 4,608 × 3,072; 3.27 MB
IT TOOK ALL OF ANDY'S COURAGE.JPG 300 × 491; 38 KB
Jacobite broadside - Prince Charles Edward Stuart disguised as Betty Burke.jpg 2,500 × 3,331; 5.53 MB
Jacobite broadside - Prince Charles Edward Stuart dressed as a lady after his flight from Culloden.jpg 2,500 × 1,999; 4.6 MB
Jindřich Mošna (foto Jan Tomáš).jpg 525 × 800; 78 KB
John amaechi.jpg 292 × 260; 22 KB
Jonathan Fortes "Du släppte mig" ÄngelCab 2013.jpg 711 × 951; 60 KB
Julian Eltinge (the fascinating widow).jpg 256 × 428; 11 KB
Julian Eltinge - 3.jpg 601 × 885; 68 KB
Julian Eltinge - 4.jpg 622 × 823; 67 KB
Julian Eltinge - Jun 1921 Photoplay.jpg 618 × 816; 71 KB
Julian Eltinge as The Crinoline Girl.jpg 237 × 300; 9 KB
Junge als Mädchen verkleidet Fastnacht Ulm c1910.jpg 402 × 624; 94 KB
Kapten Grant och hans barn, Östermalmsteatern 1908. Rollporträtt - SMV - GB073.tif 5,780 × 7,906; 87.18 MB
Kaya (迦夜, Japanese visual kei musician) in Anime Expo 2013.jpg 484 × 559; 178 KB
Kaya Salome.JPG 411 × 551; 40 KB
Kinema-Junpo-1959-April-late-2.jpg 2,402 × 2,700; 1.06 MB
Kingsley Ella.jpg 419 × 650; 38 KB
Knut Lambert, rollporträtt - SMV - H5 035.tif 2,622 × 3,983; 29.91 MB
Ladislas de Paal, un peintre hongrois de l'École de Barbizon (1904) (14589901308).jpg 1,228 × 1,814; 720 KB
Leather pants sitting.jpg 3,071 × 4,081; 3.98 MB
Leather shirt and leather mini skirt.jpg 2,786 × 3,708; 1.02 MB
Leather skirt and leather jacket crossdresser.jpg 3,072 × 4,096; 1.53 MB
Leisure and Entertainment during the Second World War A13429.jpg 800 × 611; 58 KB
Leisure and Entertainment during the Second World War A29211.jpg 800 × 614; 66 KB
Leslie Abbadini - Shakira impersonation.jpg 2,832 × 4,256; 1.19 MB
LGBT pride in Tainan 2018-03-24 01.jpg 4,608 × 3,456; 9.2 MB
Lietenant Bouley after failed escape attempt from Colditz.jpg 352 × 500; 51 KB
Logan Carter & Roxanne Russell 1975.jpg 1,000 × 492; 75 KB
Luzi Wuzi.jpg 500 × 758; 85 KB
Luzi-Wuzi.jpg 1,843 × 2,765; 1.88 MB
Madame Sans Jane (1925) - 1.jpg 590 × 802; 94 KB
Male in nightie.jpg 528 × 720; 45 KB
Mana catwalk moi meme moitie.jpg 800 × 1,200; 561 KB
Mardi Gras Bubble man wears a dress.jpg 2,420 × 2,462; 3.02 MB
Margreet Dolman.png 221 × 335; 197 KB
Margreetdolman2013.jpg 500 × 696; 291 KB
Marie Høeg utkledt som en mann, og en ukjent mann utkledt som kvinne NMFF.000418-27.jpg 1,693 × 2,504; 1.24 MB
MarignyMG073RedDragRBar.jpg 2,816 × 2,112; 2.16 MB
Marine Celebrate Crossing of the Equator, 1 July 1942.jpg 2,829 × 2,210; 3.82 MB
Mayakovsky-1910.jpg 1,400 × 1,788; 1.43 MB
Mayday-hartjesdagen2007.jpg 400 × 533; 329 KB
Men dressed in women's clothes at a picnic cricket match, Yandina, ca. 1907 (6753287397).jpg 1,000 × 748; 255 KB
Men of the 1st Battalion The King's Shropshire Light Infantry dressing for a concert party in France, 28 December 1939. O2337.jpg 800 × 602; 75 KB
Men of the 1st Battalion The King's Shropshire Light Infantry stage a concert party in France, 28 December 1939. O2333.jpg 800 × 607; 70 KB
Men of the 1st Battalion The King's Shropshire Light Infantry stage a concert party in France, 28 December 1939. O2336.jpg 800 × 609; 72 KB
Mermaid Parading 2011.jpg 3,844 × 2,991; 7.72 MB
Misa Amane Cosplay Femboy (52471617240).jpg 1,809 × 3,700; 973 KB
Monty Python Live 02-07-14 12 28 49 (14578996306).jpg 2,592 × 1,944; 1.46 MB
Monty Python Live 02-07-14 12 29 21 (14415376859).jpg 2,592 × 1,944; 1.63 MB

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