While the über fabulous RuPaul may have glamourized gender-bending drag in the '90s, a new generation of men are turning to war paint and heels to express themselves and make social statements in fascinating ways.
What's more, some of the beauty and fashion industry's biggest names are taking it mainstream.
Recently, brands have been exhibiting men in women's ad campaigns, outfitted in everything from a punch of pink polish to full-on female regalia, seemingly savoring the plush display of beauty that society has only deemed acceptable for the 'fairer' sex to explore in this modern age.
Fashion icon Marc Jacobs recently shot an Industrie spread dolled to the nines, dripping in luxe labels like Prada, Louis Vuitton -- and of course -- Marc Jacobs. Meanwhile, Serbian model Andrej Pejic sauntered down the runway as femme fatale in Jean Paul Gaultier's Fall 2011 menswear show, and decked in white tulle as the bride in the designer's Spring 2011 haute couture show.
And then there's James Franco of Spiderman fame. The actor just splashed across the second issue of Candy -- the first transsexual fashion magazine -- sporting pillowy red lips and lashes for days. Talk about a departure from the hard-bodied, cheekbone-jutting black and white beach shots Franco fronted as the face of Gucci fragrances just a couple of years ago.
Leading feminist thinker and author of the The Beauty Myth, Naomi Wolf, says that the trend reveals men -- and brands -- are increasingly questioning rigid definitions of masculinity, and embracing aspects of dress and adornment that they have had to suppress.
"This suppression is not the historical norm, even in the West," Wolf tells StyleList. "It was only about a hundred and sixty years ago that Western men stopped being the 'peacock' of the species and subjugated themselves into drab, 'straight' uniforms. I love it, it is all good. It's all about play...and play is almost always good for gender politics," adds Wolf.
If there's someone who knows a thing or two about 'peacocking,' it's Johnny Weir -- the figure-skater-turned-cultural-fashionista who regularly jaunts about in shimmery pink lipgloss and Louis Vuitton handbags. Weir just broke big beauty news by signing on as the newest face of MAC Cosmetics, who he will collaborate with on a makeup collection this upcoming holiday season, aptly titled, 'Glitter and Ice.'
Weir follows in the footsteps of fellow avante-garde trailblazers RuPaul and Elton John in modeling for the popular makeup brand, which the skater says he turns to for a stroke of confidence when putting his 'best face forward' in the public eye.
"My collaboration with MAC is very fantastically over-the-top, but I am showing the great things that makeup can create in art terms," Weir tells StyleList.
"Men need to have their 'peacock' moments as much as women - they need to feel more confident and proud of the way they look. I hope my work with MAC empowers guys to walk into MAC and actually ask the amazing artists for help," adds Weir.
It could be conceived that generations of straight-laced, corporate suit bore is what is pushing some to paint men in the opposite extreme today, which an industry like beauty and fashion is more likely to receive and embrace first -- thanks to a deep respect and reverence for personal expression.
"I think gender-bending in fashion is great, and I hope it's more than a flash-in-the-pan trend," says Feministe blogger, Jill Filipovic. "Limiting the range of ways one can adorn one's own body because 'boys don't wear lipstick' or 'girls don't wear pants' strikes me as antithetical to everything that makes fashion exciting and important," adds Filipovic.
And yet, there has been equal parts public backlash. Who could forget what the press dubbed "Toemageddon 2011," when J. Crew President Jenna Lyons appeared in the catalog painting her five year-old son Beckett's toes pink?
From decries that hot pink pedi polish could instantly turn sexual orientation, to obstinate claims that nail polish is a girl's club only accessory, the frenzied public reaction makes one wonder how much of our own meaning and personal hang-ups we're bringing to things like an inanimate bottle of lacquer.
Essie Weingarten, whose top-selling brand Essie designed the peppy Pink Parka shade featured in the controversial photo, says that nail industry insiders know that men have become a sizable portion of regular salon clientele. And it's not just a clear topcoat they're going for; a swipe of the sheer milky pink Mademoiselle shade is increasingly requested for a perceived sheen of health on finger tips.
Men who request darker or more flamboyant shades at the salon are often -- and ironically -- inspired by a very traditionally 'masculine' model.
"We're seeing experimentation with bolder colors, like Licorice and Aruba Blue, a trend that started with rock stars," Weingarten tells StyleList. "I personally believe men should wear any color that makes them feel good."
While it's not likely that men will flock in mass to paint their toenails pink and stroke on blue eye shadow, it will be interesting to see how the beauty and fashion industry's glamorization of gender mingling affects or moves the boundaries that the public finds acceptable for men to explore within.
After all, isn't it the search for freedom that brought us here?