What A Drag: Fashion’s Top 10 Gender-Bending Moments

Louis Vuitton creative director Marc Jacobs, in a pink polo dress and blinged-out pilgrim (I guess?) shoes at the opening of his exhibit Louis Vuitton - Marc Jacobs: The Exhibition at the Musée des Arts Décoratifs in Paris on March 7. I give it two weeks until we see actual polo player Nacho Figueras in this exact same outfit.

Photo: Pascal Le Segretain/Getty Images Europe

The only person who can out-do Marc Jacobs is Mrs. Marc Jacobs. This time the designer appears in full-on drag, donning a wig, makeup and high heeled pumps for this cover and inside spread of Industrie magazine. It’s also worth noting that in a match of wits, Jacobs’ left leg would totally stomp (har har) Angelina Jolie’s right leg. It’s really not even fair.

Photo: Models.com

Oh, how fashion adores its androgynous creatures. The latest poster boy is the first model to successfully walk both men’s and women’s runways in one week when he appeared at Paris Fashion Week 2011 in both Jean Paul Gaultier Spring Haute Couture 2011

Any list of fashion's top drag icons would be amiss to omit drag's unofficial pop mascot. It’s a role Lady Gaga has highly committed herself to; Jo has his own Twitter and Facebook – which, by the by, includes a bio of him as an "international 'male' supermodel" – appeared in the music video for Yoü and I, and even opened last year’s MTV VMAs. The latter appearance was particularly genius, as Gaga used a wrinkled Brooks Brothers suit and a sock in her drawers to sartorially one-up all the other female pop artists in the room – I’m looking at you, Nicki, Katy, and even Jessie J, in a heartfelt attempt to glamorize-via-bedazzlement a broken foot and crutches – who were all but completely transparent in their efforts to replicate the avant-garde trend kickstarted by Gaga herself.

Photo: Nick Knight/vogue.co.jp

Seriously, ladies, we all ought to be saying a prayer of thanks to Ms. Coco Chanel every single day we put our pants on – perhaps a mantra for each leg in the morning as we get dressed: “Thank you” for the right leg, “Chanel” for the left. The trailblazing designer was the first to point out the ridiculousness of the painful corsets and dresses women were confined to in the early 1900s, and she essentially invented the style of casual wear we all now luxuriate in during our weekend brunches and shopping jaunts. Perhaps I’m stretching the definition of “drag” a bit here, but I’m taking a cue from Ms. Chanel and giving myself room to breathe.

Photo: sarahsfashionaffair.blogspot.com

On that note, the ever-amazing Mrs. Prada paid homage to The Majesty of the Pant at Miu Miu’s Fall 2012 showing during Paris Fashion Week. Or more accurately, she went to bat for the pantsuit, another gift of Chanel's that to this day remains an integral part of the modern woman’s wardrobe, and also an excellent example of the classic female power refrain, “Whatever you can do, I can do better.” Now, who wants to get me a patterned blazer cape?

Photo: Monica Feudi/Feudiguaineri.com

And now you may kiss... the beard? A performing artist/musician/gender bender who sometimes moonlights  as a model, Benjamin Dukhan seems fairly limitless, and as such is difficult to capture in words. I’ll let his official Facebook page bio do the talking: “In 2010 Benjamin created his alter ego Burger Girl, and its 'electro-bitch' universe where sex and blood mingle with romanticism and spirituality.” Indeed, Benjamin. Indeed.

Photo: IMAXtree.com

Perhaps the first of his kind, Tanel Bedrossiantz has been walking in women's runway shows since the 1980s, making him a sort of cult classic in the fashion world. Often cited as Jean Paul Gaultier’s muse, he’s made many strong showings over the decades, but especially impressed in Gaultier’s Fall/Winter 2011 show, as the bridesmaid sashaying down the runway in a black and white all-feather floor-length skirt, not too far behind Mr. Dukhan's bride.

Photo: IMAXtree.com

This would barely count – the actor is known more for his dalliances in the world of academia than in fashion – if it weren’t for the fact that Candy, upon its launch in 2009, billed itself as “the first transsexual style magazine.” This cover instantly became an Internet sensation when it was released, depicting James Franco – shot by Terry Richardson – in bright red lipstick, blue eyeshadow, long black leather gloves, and Art Deco jewelry. The best part is that he concurrently appeared on one of the covers for GQ's December issue as their leading man of the year. Perhaps he was also wearing Gooky by Gooky.

Photo: Terry Richardson/The Huffington Post

Maybe Franco's no stranger to fashion after all. He shot this amazing spread for Elle’s July issue last year depicting Agyness Deyn – fashion’s most recent androgyny darling prior to Andrej Pejic's takeover – as James Dean. I was fully obsessed with this shoot when it came out, and not just because it’s visually pretty great, but also because it's such a mindfreak to have James Franco, who played James Dean, shoot Deyn, a female model, as the same immortal film star he once portrayed. Genius.

Photo: James Franco/Elle