Caitlyn Jenner and the Prison-House of Perfection

Lady Ellen’s finishing school in New Jersey. Photography by Joel Barhamand for Yahoo Style.

This past February, the talented photographer Joel Barhamand and I had the pleasure of attending a house party thrown by Lady Ellen, a New Jersey woman who runs a “finishing school” for male-to-female transgender folks and/or cross-dressers. We mingled with dozens of ladies from all over the region. Some of them had been openly transgender for years; some of them still only dressed up as women on the sly, for special occasions.  

They differed in style, too: Some of them clearly wanted to be bombshells, with the blondest hair, reddest lips, and highest heels possible. But many of them–particularly those who’d been living as women for years, or even decades–preferred a flattering but sensible dress, a touch of makeup and low heels or flats. They either couldn’t or had no desire to be a bombshell, to embody some hyperinflated image of femininity. Many of them had broad shoulders and torsos and straight hips. I suppose that if you wanted to cruelly deny them respect for their preferred gender identity, you could write them off as looking like, well, a man in a dress.  

I thought about these very ladies, who exhibit a quiet courage every day they hit the supermarket or the Starbucks, the other day, when I finally saw the much-anticipated Vanity Fair cover of the truly stunning-looking Caitlyn (formerly Bruce) Jenner. Shot by Annie Leibovitz, sitting pretty with flowing hair and a sculpted body encased in a fifties-style cream bodysuit, the 65-year-old Jenner looks–to borrow a term from the RuPaul’s Drag Race community–“snatched.” That is to say, flawless, buffed to a high gloss, no used-to-be-a-man giveaways. Projecting the very best version of a hot, fortysomething MILF that money and fame can buy, Caitlyn would clearly get “tens across the board” for femme realness at an old-school, Paris is Burning-style drag competition, and she certainly would’ve awed (and intimidated) the hell out of the gals at Lady Ellen’s party. 

Lady Ellen’s finishing school in New Jersey. Photography by Joel Barhamand for Yahoo Style.

And all of that is awesome–truly. The arrival of the cover this week feels like one of those seismic cultural moments, a reminder that a mere magazine cover can still push our culture into the future, as did the (belated) 1974 Vogue with Beverly Johnson as its first black model on the front, or Ellen DeGeneres' coming-out on the cover of Time in 1997.  

In terms of heralding to America and the world that being transgender is a real and authentic thing–something that is here to stay and deserving of respect and understanding–it even trumps last year’s Time magazine cover of the radiant Orange is the New Black star Laverne Cox, if only because so many more Americans have known Jenner for so much longer, and knew her for so long as an icon of male American athleticism. Every minority group deserves its pathbreaking paragon of beauty, glamor and grace, whether it’s Diana Ross or Amal Alamuddin Clooney. They’re a source of pride for the community (“Look at what we can produce”) and of aspiration (“I want to look that good, perform that well, be that special.”) 

Lady Ellen’s finishing school in New Jersey. Photography by Joel Barhamand for Yahoo Style.

And it’s clear online that a lot of the you-go-girl we’re seeing for Caitlyn derives at least in part from, well, how flawless she looks. “Yasss Gawd! Werk Caitlyn! Get it!”, Cox herself wrote on her Tumblr. At least since Jenner gave her pre-reveal interview to Diane Sawyer a few weeks ago, we’ve all been waiting to see how successfully the ponytailed Kardashian stepdad would morph into a woman–and, despite jeers from the Twittersphere’s transphobic quarters–the response is pretty clear: Caitlyn passes with flying colors. Who couldn’t help commenting on those flawlessly chiseled cheekbones, those firm and ample bosoms, those endless legs?  

"I just want Caitlyn Jenner to take me out and teach me how to drive a stick shift in heels," tweeted Lena Dunham. Hair length, facial softness, boob and hip size, and heel height are all easy ways for us to talk about going from a man to a woman. They’re a way into the conversation both for cis(non-trans)gender women, who’ve had to negotiate their entire lives how much they define themselves, or are defined by, those things, and for heterosexual men, for whom those things are often (not always, or the only) agents of attraction. 

But that’s not necessarily what being transgender is about–and, more importantly, for cisgender supporters of transgender rights like myself, that shouldn’t be our understanding of transgenderism. As Cox herself pointed out in the same Tumblr post, "There are many trans folks because of genetics and/or lack of material access who will never be able to embody these standards. More importantly many trans folks don’t want to embody them and we shouldn’t have to to be seen as ourselves and respected as ourselves.” Cox is right. Being transgender is not determined from the outside in. It’s an identity, a sense of self, that comes from deep within, and trans folks shouldn’t have to pass some visual litmus test before we deem that they deserve to be called by their preferred name or pronoun.  

Lady Ellen’s finishing school in New Jersey. Photography by Joel Barhamand for Yahoo Style.

The flip side to the gloss and glamor of the Caitlyn Vanity Fair cover–and to the fact that, on one level, it’s just the latest chapter of the Kardashians’ brilliant plot to subsume us all into the their ever-more lucrative family narrative–is that transgender people are among the most marginalized and vulnerable people in America. A landmark study a few years ago found that they suffer high levels of family rejection, discrimination, harassment poverty, unemployment, homelessness, depression and suicidal thoughts or actions. The statistics are even worse for transgender women of color, who experience shockingly high rates of violence, often fatally.  

Several years before she became famous, Cox told me in an interview that she felt truly safe only in her apartment–such was the level of daily harassment she encountered on the streets of New York City. Last year, she told me, “People think that trans women deserve violence because of this ridiculous, bullshit idea that we’re inherently deceptive…That we’re not who we say we are, that we’re fake women…’ ” 

That kind of violence–even on the verbal level of not calling a transperson by their chosen pronoun–is rooted in the idea that transness is something that must be visually earned. If someone can’t pass as flawlessly as Caitlyn–or, say, as the adorable, muscley Aydian Dowling, who may become the first openly trans guy on the cover ofMen’s Health–they don’t deserve our recognition of their chosen gender identity. 

Lady Ellen’s finishing school in New Jersey. Photography by Joel Barhamand for Yahoo Style.

But not all trans people have the resources of Caitlyn, Cox or Dowling to pass flawlessly–and, as Cox importantly points out, many of them don’t even want to. There are a million ways to express one’s internal sense of gender, only two of which include registering to the casual observer as either M or F. Though her gender experience is inarguably authentic, Caitlyn, after all, is a member of a family that has invested a good part of its seemingly limitless resources in body modification–a family for whom, when it comes to looking exactly the way they want to look (or the way they think the world wants them to look), money is no object. 

And that’s just fine. If Kim gets to be a bombshell, why shouldn’t Caitlin? (Why shouldn’t anyone, for that matter?) And say what you will about the Kardashians, they know how to stand by one another as a family. “Be happy, be proud, live life YOUR way!”, Kim tweeted at Caitlyn after her big reveal.  

So remember that the next time you see a “man in a dress,” even if she’s not as snatched as Caitlyn. That’s actually a human being courageous enough to live her truth in a society only beginning to understand her. She may not have a magazine cover and a stylist, but she still deserves a you-go-girl! 


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“It’s About Stripping Down In An Elegant Way,” Stylist Jessica Diehl On Dressing Caitlyn Jenner

From Bruce to Caitlyn: How to Properly Address Transgender Topics