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45 Examples of Cross-Dressing Styles

Robin Williams in Drag Makes for Classic Career Performances

— September 18, 2013 — Pop Culture
Robin Williams in drag made the 1990s classic Mrs. Doubtfire. To celebrate the comedian's return to television, this collection looks at other instances of cross-dressing, whether it was for comedic effect, or to be provocative or to raise awareness.

In fashion, photography gender-swapping is a common concept, whether it involves women dressed in menswear, or men in dresses or other feminine apparel. This can be seen in lower end ads or in haute couture. On the advertising side of things, cross-dressing is often used as a shock and awe tactic.

Celebrities and other recognizable characters also wear the clothing typically associated with the opposite sex. Robin Williams in drag is a great example of this, which can be seen in Re-Cut Comedy Classics and Movie Songstress Hybrid Blogs.
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Score
Popularity
Activity
Freshness
45
Re-Cut Comedy Classics
Re-Cut Comedy Classics
The Mrs. Doubtfire Horror Trailer Makes You Rethink Childhood
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44
Movie Songstress Hybrid Blogs
Movie Songstress Hybrid Blogs
The 'What if Adele was Mrs. Doubtfire' Tumblr is Hilarious
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43
Gender-Bending Rapper Impersonations
Gender-Bending Rapper Impersonations
This BET Award Show Promo Features a Cross-Dressing Samuel L.
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42
Fabled Gender-Swapping Prints
Fabled Gender-Swapping Prints
Yudi Chen Switches Gender Roles in His Playful Fairy Tale Paintings
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41
Cross-Dressing Portrait Photography
Cross-Dressing Portrait Photography
Jill Peters Captures an Ancient Albanian Tradition
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40
Conceptual Headpiece Captures
Conceptual Headpiece Captures
The Benjamin Benedek by Verena Mandragora Image Series is Sculptural
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39
Gender-Bending Masculine Portraits
Gender-Bending Masculine Portraits
Chad States Has Created a Personal Depiction of Masculinity
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38
Cancer-Combating Cross-Dressing
Cancer-Combating Cross-Dressing
The ‘Tutu Project' Raises Awarenes by Turning Heads
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37
Obscured Gender Photoshoots
Obscured Gender Photoshoots
The Le Melange Des Genres Editorial is Indeterminate
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36
Poker Reality Shows
Poker Reality Shows
Gambling Takes On New Heights With 'Two Months Two Million'
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35
Provocative Gender-Bending Editorials
Provocative Gender-Bending Editorials
'Kings and Queens' is Well Shot and Original
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34
Transgender Alcohol Ads
Transgender Alcohol Ads
The Bearded Lady Bourbon Campaign Urges People to 'Stay Strong'
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33
Hilarious Gender-Bending Portraits
Hilarious Gender-Bending Portraits
These Funny Photos Capture Men Wearing Ladies Clothing
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32
Gender-Bending Celebrity Editorials
Gender-Bending Celebrity Editorials
Jared Leto Gets Dressed in Drag for This Candy Magazine Shoot
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31
Feminine Fella Photography
Feminine Fella Photography
'Un Garcon' from Mariya Sabotinova Shows the Soft Side of Male Fashion
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30
Cross-Dressing Adverts
Cross-Dressing Adverts
The Leo Burnett 'Art Directors Club Ukraine' Campaign Bends Gender Lines
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29
Gender-Bending Fashion Photography
Gender-Bending Fashion Photography
This Series Features a Male Model Draped in Flowers and Makeup
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28
Cross-Dressing Monarch Photography
Cross-Dressing Monarch Photography
The Chan-Hyo Bae 'Existing in Costume' Series Takes on History
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27
Cross-Dressing Brand Reps
Cross-Dressing Brand Reps
Dame Edna Launches Limited-Edition MAC Cosmetics Collection
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26
Old Hollywood Cross-Dressing
Old Hollywood Cross-Dressing
Piers Atkinson Spring/Summer 2010 Line is Modeled by a Man
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25
Cross-Dressing Smokers
Cross-Dressing Smokers
Dan Felton Rocks Women's Lingerie for Matthew Kristall Shoot
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24
Cross-Dressing Couple Photos
Cross-Dressing Couple Photos
Sincerely Hana Pulls a 'Switcheroo' on Her Fun-Loving Audience
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23
Gender Role-Switching Photography
Gender Role-Switching Photography
Arvida Byström Captures Boys Doing Girl Things for VICE
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22
Selling Cars with Drag Queens
Selling Cars with Drag Queens
Renault Twingo Cross-Dressing Commercial
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21
Cross-Dressing Collections
Cross-Dressing Collections
'Acne' Transvestite Shirts are Fashionably Gender-Bending
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20
Gender-Defying Models
Gender-Defying Models
Casey Legler Becomes the First Female Signed On as a Male Model
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19
Cross-Dressing Masked Wrestlers
Cross-Dressing Masked Wrestlers
Mexico's 'Lucha Libre' Troupe
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18
Heel-Wearing Man Shoots
Heel-Wearing Man Shoots
Giampaolo Sgura Shoots a Crew of Men in Purses and Pumps
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17
Drag Queen Barbies
Drag Queen Barbies
The Blonds Blond Diamond Doll Makes Cross-Dressing Super Glamorous
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16
Gender-Changing Editorials
Gender-Changing Editorials
The Pani September 2012 Editorial Stars a Magdalena Frackowiak
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15
Cross-Dressing Couture
Cross-Dressing Couture
Dolled Up Callum Wilson in Candy Magazine Rocks Christian Lacroix
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14
Feminized Male Actors
Feminized Male Actors
The Worth1000 Gender Bending Contest Mashes Two Celebs Together
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13
Gender-Switched Pregnancy Ads
Gender-Switched Pregnancy Ads
Thses Ads for the City of Chicago Show Impregnated Teenage Boys
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12
Couture Cross-Dressing
Couture Cross-Dressing
Karl Lagerfeld Shoots Baptiste Giabiconi in Women's Clothing
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11
90s Cross-Dressing
90s Cross-Dressing
‘Fall For Heidi' in V Magazine
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10
Ball Gown Sporting Jocks
Ball Gown Sporting Jocks
Major League by Emmanuel Giraud Puts Outfielders in Frocks
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9
Circus Freak Fetes
Circus Freak Fetes
Mariano Vivanco Shoots Un-Conventional Models for Hercules Issue 9
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8
Cross-Dressing Pictorials
Cross-Dressing Pictorials
The Multi-Model Editorial, 'New Faces' in French Revue De Modes
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7
Cross-Dressing Gentleman Portraits
Cross-Dressing Gentleman Portraits
The David Prat by Sylvain Norget Editorial Blurs Gender Roles
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6
Cross Dressing Husbands
Cross Dressing Husbands
Olympia Sock Ads: Lingerie For Your Feet
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5
Gender Swap Suits
Gender Swap Suits
The Virtual Transgender Suit Provides Instant Change
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4
Cross-Dressing Princess Cartoons
Cross-Dressing Princess Cartoons
Haruki Godo's 'Costume Swap' has Disney Characters Trade Clothes
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3
Men in Sheer Dresses
Men in Sheer Dresses
Cross-Dressing Simon Nessman Appears in Tokion Magazine
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2
Cross-Gender Cosplay Captures
Cross-Gender Cosplay Captures
Male to Female Crossplay Photos by Naoko Tatibana are a Taboo
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1
Cross-Dressing Fashion Ads
Cross-Dressing Fashion Ads
Marc Jacobs Puts Male Model in Women's Clothes
<