Gendered clothing is an age-old concept, but thanks to the global phenomenon of RuPaul's Drag Race - and an overall increase in LGBTQ cultural visibility - the notion of subverting those clothing norms has rapidly expanded within the mainstream like never before. Impersonating another gender is a key cornerstone of queer culture - drag is not only a high art form but is also a valuable tool for dismantling the gender binary. Outside of these circles, however, drag and gender-bending attire have never been taken particularly seriously.
From Some Like It Hot to Tootsie to She's the Man, gender-bending is a frequent trope in romantic comedies because it often harvests an easy laugh from those unfamiliar with the practice. Similarly, cartoons and children's entertainment have done the same for decades. From The Simpsons to SpongeBob SquarePants, there's a very high chance that many of your favorite childhood characters have dressed outside the typical gender norms at least once, and for a lot of LGBTQ kids, this slim glimmer of representation may have been a formative experience.
Bugs Bunny dabbled with gender-bending attire so often during his early years that his hobby was practically a full-blown lifestyle. Usually, Bugs's sartorial shenanigans were used to bait other male characters, particularly his hunting antagonist Elmer Fudd, who inevitably fell for the rabbit's sultry disguises.
Unfortunately, the Warner Bros. mascot's hobby petered out as he progressed further into his decades-long history, but his influence was nevertheless far-reaching. "Bugs Bunny was my first introduction to drag," drag show superstar RuPaul Charles said in 2016. "As a kid I always dressed in everything. I would use all the tools available as a human to express myself. No sexual connotation to it. It was just stuff."
Every '90s kid remembers the iconic bearded and booted nemesis of the Powerpuff Girls, HIM. Armed with a set of lobster claws and a fur-trimmed dress, the speed demon is frequently cited as one of the era's greatest cartoon villains because of his perfectly balanced mix of terror and humor.
The Powerpuff Girls also deserves kudos for not creating a connection between gender-bending and villainy. Instead, HIM's other unique characteristics were the root cause of his disturbing nature. Writer Morgan Turano claims, "What makes HIM so unsettling... isn't his gender-bending persona. Rather, HIM is creepy because he is a combination of opposites - Santa and Satan, snake-like curves and sharp points, person and clawed beast. Even his voice is half singsong and half unchecked rage."
Many children's shows and movies feature elements of gender-bending, but there are few whose entire plots center around the concept. Mulan, Disney's take on one of China's most famous historical figures, sees a young woman pose as a male warrior in order to spare her aging father from returning to the battlefield.
Two decades after Mulan's release, VICE's Zing Tsjeng said the film has become "a cultural touchstone for a whole generation of Asian LGBTQ people around the world."
As planet Plorgonar's foremost Earth expert, Agent Wendy Pleakley quickly adopts much of our planet's culture when he's sent to recover Experiment 626 in Lilo & Stitch. Specifically, he gravitates towards more traditionally feminine pursuits, including women's fashion, which he finds to be far more inspiring than that of Earth men.
Initially, his choice to don skirts rather than pants is chalked up to his three-legged physique. By the time of the spinoff series, however, Pleakley's consistent interest in wigs and makeup has clearly reached far beyond mere practicality.