What We Wear to Work//

I’ve Dressed for Work as a Man and as a Woman — Here’s What I’ve Learned

"That part of who I was, the truest, most fundamental part, was hidden away behind an increasingly masculine persona."

Image by Magdalena Kleemann/ Getty Images

The culture of work is changing, and with it, our office dress codes. As companies encourage staffers to bring their whole selves to work — and people embrace style repeats and “personal uniforms” in an effort to de-stress workwear — Thrive decided to take a deeper look into how what we wear to work affects our mental well-being, creativity, productivity, and authenticity. We welcome you to take a spin through our special section: The Psychology of What We Wear to Work

As a man, dressing for work was easy. Actually, dressing for anything was easy. I could do my hair or not, I could wear the same pants as yesterday, or not, or I could close my eyes, dig through the pile of clothes on my floor, and put on the first thing I found. At the end of day, it absolutely did not matter, because men get to wear whatever they want, it would seem, and remain impervious to criticism. For me, however, that all changed when I finally decided to transition from male to female in the Spring of 2016, just before my twenty-ninth birthday.

In retrospect, I have always been a woman, but, as a child of the 90’s, I received the damagingly stereotypical messaging of masculinity passed down to my father and his peers from the men of the Greatest Generation. So, despite my desire to be feminine at a young age and despite having recurring dreams of being in a girl’s body, I adopted the male visage, because I was told to. I had my outlets, of course — I began crossdressing in secret in the third grade, and I almost always chose a female character in video games — but that part of of who I was, the truest, most fundamental part, was hidden away behind an increasingly masculine persona. Times changed, thankfully, and the internet exposed me to a world broader and more diverse than I could ever have imagined. It was in that digital milieu that I came to know the stories of women, who after being assigned male at birth, finally embraced their unusual biology to live out a more authentic and fulfilling existence a world away from the torture of maintaining a physically unbearable facade for the benefit of others.

Given that I was socialized under such circumstances, I found it incredibly surprising when friends and coworkers at a previous employer began commenting on my clothing, specifically whether or not what I was wearing would be considered inappropriate. Never once, in my twenty-eight years as a man, had anyone ever suggested such a thing, yet, now, as a woman, I was supposed to modify my appearance to meet some standard that was as elusive as it was vague? The notion, to me, was ludicrous. And while I wish I could say that I did not succumb to the pressures of such unequal judgement, the truth is that those comments began to shape me. Where once I felt free to dress as I saw fit, I now felt fearful that wearing outfits that made me feel confident would jeopardize my job.

So, for some months, I toned it down: less skin, regardless of it being a hot summer; less dramatic eye makeup, for fear of looking too sexy; less me, for fear of being cast out. Meanwhile, my male colleagues at my first office-based software engineering job continued to make lewd jokes in sandals and shorts with their guts hanging out over their belts and their boxers and butt cracks making cameos in the midst of our meetings.

It was a sad time for me, as I never truly felt like myself. I felt like I was playing a role. And while I enjoy acting, I don’t get paid to; I get paid to code, and I code best when I feel like a bad bitch wearing crop tops and jean shorts on hot, humid days. I would rather die than have to live another day where I cannot fully express who I am, and that’s exactly what I did. I put my middle fingers up, wore the clothes that I wanted, and kicked ass at my job, as a woman. And guess what? No one fired me, the world did not end. I still relish the opportunity to challenge and shape the views of corporate America and its policies regarding dress code. For it is in moments of discomfort that we grow, evolve, and move forward as something greater than we once were — take it from a woman who has endured the pain wrought by scalpels and bone saws to simply be called “ma’am” when answering her door or standing in line at the grocery store. Because at the end of the day, what do we value more — what we wear, or what we do?

The age of conformity is over. The era of identity is now, and nothing has confirmed this for me more than the journey I have taken as I have transitioned from male to female over the past couple of years. I stand in front of the mirror every day, examining my sartorial selections and proudly facing the world in an armor of my own decisions. Every piece of clothing, every touch of makeup, every inch of myself has been labored over with a scrutiny that serves a singular purpose: to communicate to the world that while I was assigned male at birth, I am very much a woman, and I will not curb the vision of my femininity for even a single second more than I already have.

So, whether in high tops or heels, yoga pants or pencil skirts, when I leave my apartment in the morning to head to work, I am me, and I want you to be you. And if you are feeling timid, don’t, because as my coworker Lisa said to me once, “I was worried about what I was wearing this morning, but then I remembered that you would be wearing less,” and if I can excel in my career — as an ostentatious trans woman forcibly well-versed in the psychology of men — then so, too, can we all.

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More on the Psychology of What We Wear to Work:

7 Lessons from Jonathan Van Ness and DVF About Life, Confidence and Fashion

5 Fashion Tips to Get Out the Door 20 Minutes Faster

Rethinking Your Work Style After Maternity Leave 

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