The Cross Dresser on the Ramparts of Change

This post has been fermenting in the recesses of my brain for some time now, and has been uncorked in part as the result of a recent post on Gabrielle Hermosa’s blog. There, you will see the old pictorial of our species emerging from the muck, slowly shaking off fins, sprouting limbs and finally assuming a decidedly female form at the natural end of our possible progress. Nice bag in hand too.

Many of you are old enough to remember parts of the sixties. One of the more memorable cultural events of this tumultuous time was what was then known as the “Women’s Lib” movement. From a fashion perspective, things started off poorly in my mind with bra burnings. Tragic as the loss of countless innocent foundation garments to the angry bonfires of revolution was, change was clearly in the air, and change and I are old friends.

The bra burnings were a stunt, but there is always a kernel of substance within a stunt. The substance of the movement was that the rules were stacked unfairly in favor of the fellows, and that much needed to change. Broad challenges to gender role definitions and the status quo here and abroad were accepted and engaged.

Laws did, and continue still, to change. Most public sector and many private sector employers adapted their organizations to remove barriers to success in the workplace. Academic life here stateside was forever changed by the adoption of NCAA Title 9 rules mandating equal funding of women’s athletic programs. Elementary school curricula changed to mitigate gender biases in approaches to education. New role models in media, and on the streets we grew up on emerged. And new generations have been born and grown to adulthood with a different set of gender ideals and expectations than the ones we slightly greyer folk inherited in our youth. All good, and mostly great in my view.

Women now more commonly occupy more senior positions in more industries. A majority of college students in this country are female. The industries that depend on muscle-power are dead or dying. The industries that depend on brain-power are (relatively) thriving. Yes, wage gaps and all manner of subtle and not so subtle barriers to full and equitable participation remain, but those barriers are under siege everywhere. Again, hurray, says I.

Change has rough edges. Fashion for some time favored mannish fabrics, curve free silhouettes, and dull pallets. God awful shoulder pads even had their day. Overt displays of femininity, both behavioral and on the surface or were penalized. Avoiding the suspicion that the successful women was either dazzling or sleeping their way to the top was job one. We seem to have thankfully emerged from the worst of that. Femininity, surface or otherwise, is not inconsistent with success. All of this is arguable of course, and forgive me my broad brush strokes here. They are in service of a point. You ready?

The validity and the value of the female experience is sought, accepted and acted on, on it’s own natural terms more now than at any time in my experience. I suspect that this trend will continue. As it does, as the pendulum swings, as tides reverse, as societal plates shift and groan (ed. and as my metaphor hip-check the crap out of each other) a certain amount of displacement is bound to happen. The value and the necessity of a purely, brawny, traditionally male skill and sensitivity set is bound to diminish. We already feel this reality in many aspects of our daily lives.

My wonderings on the matter go like so: Do men more inclined, as I am, to discover surface and interior elements of our “femininity” have a shaved leg up on the competition?

This is a serious question. I am not interested in a revolution that makes it acceptable for me to take a meeting in a pair of heels rather than a nicely tooled brogue. I am not interested in working for an organization where my ability to mount the org chart (figuratively, dear friends) is dependant on my ability to smartly accessorize a pencil skirt and blouse ensemble. I am interested though, in providing value, and getting paid for it, where the demand is greatest, where my competition is disadvantaged, and where my skill sets are well adapted for the need.



I have a client whose customers are 99% female. The founder and CEO of the organization is about my age. Her prototypical customer has a college education, leads a growing family, and has growing economic power. The product my client sells to her client is a highly emotionally charged gift. Men do not get it, or buy it. I strategize with my client on how to engage better with her perfect prospective customer.

I am the only male outside consultant / contributor to her businesses growth. My client has commented, surprisedly, that I “get” the business, and that I understand her customer. This is a key to my continued utility. This reinforces a personal belief I have that the Cross Dressing is merely a surface aspect of a bigger, whole, true me. This really makes me happy and then I want to go shopping with my client. But not really. OK, I do. I could help her out a little. In the meantime, we are able to help each other out with our businesses in a way that could not have happened 20 years ago.

I do not have 20 years of work ahead of me, but you might have.

So dear friends, over to you. Do you believe there is something that you have, beneath the surface, integral to your worldview that you can leverage to your benefit? Are you better enabled than most of your workmates to understand women, work with them, work for them, learn from them, and make their world better? Does your secret endow you with secret powers?

Comments welcomed, as are business referrals if a marketing consultant with a uniquely cultivated view of the female consumer is required.