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.
45 Examples of Cross-Dressing Styles
Robin Williams in Drag Makes for Classic Career Performances:
Alyson Wyers — Sep 18, 2013 — Pop Culture
45
Cross-Dressing Princess Cartoons
Haruki Godo's 'Costume Swap' has Disney Characters Trade Clothes
44
Gender-Defying Models
Casey Legler Becomes the First Female Signed On as a Male Model
43
Cross-Dressing Fashion Ads
Marc Jacobs Puts Male Model in Women's Clothes
42
Gender-Switched Pregnancy Ads
Thses Ads for the City of Chicago Show Impregnated Teenage Boys
41
Feminized Male Actors
The Worth1000 Gender Bending Contest Mashes Two Celebs Together
40
Cross-Dressing Monarch Photography
The Chan-Hyo Bae 'Existing in Costume' Series Takes on History
39
Cross-Dressing Gentleman Portraits
The David Prat by Sylvain Norget Editorial Blurs Gender Roles
38
Men in Sheer Dresses
Cross-Dressing Simon Nessman Appears in Tokion Magazine
37
Couture Cross-Dressing
Karl Lagerfeld Shoots Baptiste Giabiconi in Women's Clothing
36
Cross Dressing Husbands
Olympia Sock Ads: Lingerie For Your Feet
35
Hilarious Gender-Bending Portraits
These Funny Photos Capture Men Wearing Ladies Clothing
34
Circus Freak Fetes
Mariano Vivanco Shoots Un-Conventional Models for Hercules Issue 9
33
Cross-Dressing Couture
Dolled Up Callum Wilson in Candy Magazine Rocks Christian Lacroix
32
Heel-Wearing Man Shoots
Giampaolo Sgura Shoots a Crew of Men in Purses and Pumps
31
Drag Queen Barbies
The Blonds Blond Diamond Doll Makes Cross-Dressing Super Glamorous
30
Selling Cars with Drag Queens
Renault Twingo Cross-Dressing Commercial
29
Gender-Bending Fashion Photography
This Series Features a Male Model Draped in Flowers and Makeup
28
Cross-Gender Cosplay Captures
Male to Female Crossplay Photos by Naoko Tatibana are a Taboo
27
Cross-Dressing Collections
'Acne' Transvestite Shirts are Fashionably Gender-Bending
26
Gender-Bending Celebrity Editorials
Jared Leto Gets Dressed in Drag for This Candy Magazine Shoot
25
Cross-Dressing Adverts
The Leo Burnett 'Art Directors Club Ukraine' Campaign Bends Gender Lines
24
Gender-Changing Editorials
The Pani September 2012 Editorial Stars a Magdalena Frackowiak
23
Gender Role-Switching Photography
Arvida Byström Captures Boys Doing Girl Things for VICE
22
Gender-Bending Masculine Portraits
Chad States Has Created a Personal Depiction of Masculinity
21
Feminine Fella Photography
'Un Garcon' from Mariya Sabotinova Shows the Soft Side of Male Fashion
20
Ball Gown Sporting Jocks
Major League by Emmanuel Giraud Puts Outfielders in Frocks
19
Cross-Dressing Pictorials
The Multi-Model Editorial, 'New Faces' in French Revue De Modes
18
Provocative Gender-Bending Editorials
'Kings and Queens' is Well Shot and Original
17
Old Hollywood Cross-Dressing
Piers Atkinson Spring/Summer 2010 Line is Modeled by a Man
16
Gender Swap Suits
The Virtual Transgender Suit Provides Instant Change
15
Cross-Dressing Masked Wrestlers
Mexico's 'Lucha Libre' Troupe
14
Cross-Dressing Smokers
Dan Felton Rocks Women's Lingerie for Matthew Kristall Shoot
13
90s Cross-Dressing
‘Fall For Heidi' in V Magazine
12
Cross-Dressing Brand Reps
Dame Edna Launches Limited-Edition MAC Cosmetics Collection
11
Transgender Alcohol Ads
The Bearded Lady Bourbon Campaign Urges People to 'Stay Strong'
10
Obscured Gender Photoshoots
The Le Melange Des Genres Editorial is Indeterminate
9
Cross-Dressing Portrait Photography
Jill Peters Captures an Ancient Albanian Tradition
8
Cross-Dressing Couple Photos
Sincerely Hana Pulls a 'Switcheroo' on Her Fun-Loving Audience
7
Cancer-Combating Cross-Dressing
The ‘Tutu Project' Raises Awarenes by Turning Heads
6
Gender-Bending Rapper Impersonations
This BET Award Show Promo Features a Cross-Dressing Samuel L.
5
Conceptual Headpiece Captures
The Benjamin Benedek by Verena Mandragora Image Series is Sculptural
4
Fabled Gender-Swapping Prints
Yudi Chen Switches Gender Roles in His Playful Fairy Tale Paintings
3
Re-Cut Comedy Classics
The Mrs. Doubtfire Horror Trailer Makes You Rethink Childhood
2
Poker Reality Shows
Gambling Takes On New Heights With 'Two Months Two Million'
1
Movie Songstress Hybrid Blogs
The 'What if Adele was Mrs. Doubtfire' Tumblr is Hilarious
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80s Football-Inspired Collections
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Nostalgic Toy-Inspired Fashion Collections
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Naughty Holiday Campaigns
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Stylish Performance Uniforms
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2-in-1 Fashion Dolls
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Masculinity-Exploring Fashion Collections
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Fantastical Hyper-Utility Fashion Liness
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Digital Streetwear Collaborations
The Fabricant x Highsnobiety Dropped During Paris Fashion Week
Cartoon Characters-Themed Apparel
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Jamaican Artist-inspired Fashion Lines
Bianca Saunders & Farah Tapped Lee “Scratch” Perry's Legacy
Nudist-Themed Sporty Fashion Campaigns
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Filmic Skater Shoes
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Outlandish Bear-Inspired Pants
Doublet's 'The Bear Carrying on You' Faux-Fur Trousers are Insane
60s Hippie Culture-Inspired Fashion
LMC Presents the Peace, Freedom, and Reversal Capsule for SS23
Celebrity-Fronted High Fashion Campaign
Marc Jacobs Enlists Kate Moss for the FW22 Resort Campaign
Sporty Visual Fashion Campaigns
PUMA and NOAH Join Forces on a New Sporty Campaign Series
Sitcom-Themed Clothing Collections
The Percival x Seinfeld Collection Has Recognizable Styles
Avant-Garde Fall Menswear
Rick Owens Unveils the LUXOR Collection for Fall/Winter 2023
Modern Women-Exploring Luxe Fashion
The Fendi SS24 Series was Unveiled on the Runways
Humorous Collab Fashion Campaigns
Barbour and Maison Kitsuné Launches a New Campaign
British Tradition-Themed Fashion
Charles Jeffrey LOVERBOY Presents These New Caroleans
Historic Fashion Try-Ons
The Design Museum's London Fashion Exhibition Integrates AR Mirrors
Loud Luxury Fashion
Moschino SS24 Pokes Fun at "Quiet Luxury" with Maximalist Styles
Sci-Fi Film-Inspired Fashion
sacai Honors Christopher Nolan with the Interstellar Collection
Star-Studded Luxe Fashion Campaigns
Alexander McQueen Presents its Dramatic FW23 Campaign
Collaboration American Brand Sleepwear
The Macy's x Gap Collection Has Options for Men and Women
Digital Holiday Dresses
Bershka x DressX Digital Going Out Collection Targets Gen Z Customers
Inclusive Fashion Runways
The Runway of Dreams Foundation Returns for New York Fashion Week
Runway-Inspired Fashion Dolls
New York Fashion Week Designs Inspire the L.U.V. Fashion Doll Styles
Romantic Fashion-Forward Apparel
PrettyLittleThing Offers a Range of Apparel Perfect for Vday
Tennis Icon-Inspired Collections
Wilson Sportswear's Modern Icons Collection is Performance-Driven
Drag-Inspired Fashion Shows
Ervin Latimmier's Spring/Summer 2024 Embraces a Drag Narrative
Chic Mother-Daughter Apparel
The Newest Never Fully Dressed Collection is an Ode to Nostalgia
Narrative-Driven Fashion Lines
The Outlier by Willie Norris Spring/Summer 2024 Theme is ‘Escape’
Celebrity-Fronted Fashion Campaigns
The New Calvin Klein Campaign Features Many Celebrities
Hip Hop Fashion Exhibitions
MFIT Presents Fresh, Fly, and Fabulous: Fifty Years of Hip Hop Style
Celebratory Disney-Inspired Collections
Forever 21 Celebrates Disney's 100th Anniversary
Chic Streetwear Fashion Collections
Homme+Femme Recently Debuted Its Spring/Summer 2023 Line
Proportion-Exploring Mystical Menswear
Alexander McQueen Presents His Intricate SS24 Collection
Actor-Designed Workwear Collections
The Ford x Sydney Sweeney Collection Reimagines Workwear
Spring-Ready Sophisticated Streetwear
Kith Spotlights Bryan Cranston in the Spring '23 Collection
Makeup-Free Fashion Campaigns
Pamela Anderson's Fresh Face Stars in Proenza Schouler's 2024 Shoot
Detailed Filmic Fashion Publications
'Barbie: The World Tour' Breaks Down Outfits from the Film
Phygital Fashion Brands
PUNK Challenges Conventions with Digital Assets & Physical Tracksuits
Inaugural Womenswear Collections
Bode Takes a New Direction with a Full-On Womenswear Capsule
Humanitarian-Inspired Luxe Fashion Campaigns
Prada Presents In Conversation with a Flower for FW23
Portugal-Inspired Spring Fashion
Drôle de Monsieur Introduces its New Collection for SS23
Luxurious Dreamy Fashion Collections
Dior and ERL's California Couture Range is Making a Splash
Historical Doll-Themed Wardrobes
Consumers Can Rent Barbie's Dream Wardrobe Through Selfridges
Charismatic Traditional Spring Fashion
Charles Jeffrey LOVERBOY Drops STATANT PASSANT RAMPANT
Socialite-Inspired Toy Dolls
Bratz Adds New Red Carpet Styles to its Kylie Jenner Collection
Self-Referencing Fashion Collections
For Fall/Winter 2023, UNDERCOVER is Reimagining Old Design
Nostalgic Fragrance Campaigns
Impulse & Frankie Bridge Faithfully Recreated Iconic 90s Looks
Doll-Inspired Kids Collections
The PatPat x Barbie Collection Features About 60 Unique Styles
Trans Kidney Health Ads
Africa Creative's Ad Sheds Light on Trans Community's Kidney Health Burden
Empowering Fashion Films
Victoria's Secret World Tour Reimagines the Iconic Show as a Feature Film
Nostalgic Classic Reissued Garments
The Wrangler Reissue Collection Celebrates 75 Years
Androgynous Resort Fashion Capsules
Edward Crutchley Presents his Latest Resort Capsule
Iconic Artist-Adorned Jeans Lines
The Lee x Jean-Michel Basquiat Capsule is Effortlessly Stylish
Chinese Erotica-Inspired Spring Fashion
Chet Lo Presents a New Collection for SS24 During LFW
Shoppable Luxury Fashion Films
Tom Ford Allows Consumers to Seamlessly Shop Its Spring 2024 RTW
High School-Inspired Autumn Fashion
ERL Presents a Look at its FW24 Collection of Retro Themes
Reimagined Hybrid Futuristic Sportswear
LUEDER Presents Hybrid Looks for SS24 During LFW
Painter-Honoring Apparel Collections
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Rolling Paper Apparel Collections
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Happiness-Celebrating Fashion Campaigns
Prada's Memories of Beauty Salutes the Year of the Rabbit
Retro Italian-Inspired Fall Fashion
Martine Rose's FW23 Collection is Sexy, Very Sexy
Sleek Sporty Undergarments
Lacoste's Women's Underwear Capsule Is Inspired by the Brand's Legacy
Cheerful Spring-Ready Collaborative Fashion
Diane von Furstenberg Works on a Capsule with Target
Multifaceted Swimsuit Cover Models
Sports Illustrated Swimsuit Enlists Martha Stewart on its Cover
North African Culture-Inspired Fashion
Daily Paper's Under the Same Moon Series Readies for SS23
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Lacoste and Netflix Unveil New Apparel Collection
Spring-Ready Fashion Editorials
The Garbstore Presents its New Campaign for the SS23 Season
Cartoon-Inspired Fashion Capsules
Fred Segal Launches a Betty Boop-Inspired Collection
Girlhood-Inspired Clothing Drops
Peachy Den's 'Sweet Cheeks' Collection Pays Homage to Girlhood
Romantic Narrative-Inspired Fashion
Edward Cuming Unveils a New Capsule for the SS24 Season
Villainous Comic Character Makeup
The Revolution Beauty x DC Super-Villains Collection is Playful
British Nightlife-Inspired Fashion
Martine Rose's Spring/Summer 2024 Collection is Eye-Catching
Childhood Carnival-Themed Fashion
Gerrit Jacob Unveils its New Collection for the SS24 Season
Nostalgic Shopping Ads
The Rakuten Big Game Campaign Revives Alicia Silverstone as Cher Horowitz
Collaborative Gorpcore-Themed Apparel
IVY PARK and adidas Continue to Grow its Expansive Capsule
Inflatable Spring-Ready Latex Clothing
HARRI's SS23 Capsule of Latex Apparel is Available Now
Empowering Movie Industry Dolls
Mattel's 2024 Career of the Year Barbies Celebrate Women in Film
Model-Inspired Fashion Collections
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Chic Puffer Jacket Designs
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Vintage-Inspired Fashion Collaborations
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Chessboard-Themed Apparel Collections
UNDERCOVER's Collection is Inspired by Music Album Covers
Cargo-Honoring Fashion Campaigns
Peachy Den Highlights its Mimi Cargo Pants in a Campaign
Collaborative Penny Loafer Collections
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Individualism-Focused Apparel Capsules
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Designer-Approved Western Apparel
Dapper Dan Debuts a New Spring Collection with GAP
Irish Folklore-Inspired Fashion
UNDERCOVER Presents its New Collection for the SS24 Season
Creature-Themed Graphic T-Shirts
Mr Jones Watches Debuts its First Line of Unisex T-Shirts
Reworked Upcycled Streetwear Capsules
clothsurgeon Presents the Changing of the Guard Collection
Cinematic Thriller-Inspired Runways
Kubrick's Eyes Wide Shut Inspired the Jw Anderson FW 2024 Show
Men's Holiday Pajamas
Chubbies Launches a Range of Iconic Holiday Pajama Outfits
Label-Backed Musical Merch
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Sleek High-Fashion Eyewear
COS Launches an Iconic Eyewear Collection with Linda Farrow
Record-Breaking Drag Brunches
H&M Broke a Record for the "Most People Attending a Drag Brunch"
Cat-Adorned Streetwear Styles
Puma Unveils its Collaborative Collection with RipNDip
Play Kidcore Games
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Color-Changing Fall Fashion
Anrealage Unveils New Clothing Designs at Paris Fashion Week
Cartoon-Inspired Fashion House Tributes
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Sleek Seasonally Transitional Fashion
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Debut Womenswear Collections
Johnnie-O Launches a New Women's Line Composed of Everyday Essentials
Bridal Wig Collections
The UNice Bridal Collection Shares Timeless, Romantic & Modern Styles
Collaboration Springtime Clothing Collections
Diane von Furstenberg for Target Has Over 200 Pieces
Celebrity-Backed Outdoor Apparel
Martha Stewart Debuts an Apparel Line with Tractor Supply Company
Metamorphosing Fall-Ready Fashion
DZHUS Presents its New Seasonal Transit Collection
Liberated Airway Dress Codes
British Airways Encourages Its Crew to Be Their Authentic Selves
Womenswear Wardrobe Staples
JD Williams Debuts a Versatile Clothing Capsule for Middle Age Women