WHY I Wore a Dress For the First Time

Was Embracing 'Femininity' Good For a Detransitioned Woman?

In my earlier years, I harbored misconceptions about femininity. I believed that wearing dresses, makeup, or anything deemed "feminine" was tantamount to surrendering to societal stereotypes. It felt like I would be relinquishing my identity, bowing to external pressures, and conforming to a predefined image of womanhood that I vehemently rejected.

When I detransitioned from living as a ‘gay transgender man’ in 2019, I was confronted with the rawest aspect of myself—my biology, and the damage my radical double mastectomy had inflicted. At 22, I began a new chapter of my journey to self-acceptance. For 4 years I deprogrammed from the internalization of misogyny which harbored anxiety about ‘signaling femininity.’ In my self-loathing, I believed that weakness, shallowness, or objectification was what women’s fashion was. I allowed these misconceptions to dictate my choices, creating a self-imposed barrier that kept me from embracing a fuller spectrum of self-expression.

But life has a way of surprising us. Over time, my perspective shifted, like a kaleidoscope revealing new patterns and colors. I began to understand that femininity wasn't synonymous with weakness; it was a celebration of creativity inspired by the female form. It wasn't about adhering to predefined roles, but about embracing one's natural body authentically.

So at 26, my official entrance into ‘capital A’ Adulthood vs ‘emerging adulthood’, I chose to wear a dress for the first time. I had experimented with wearing shorts and tees designed for girls, picking out funky looks in the women’s section of Goodwill instead of the (far more boring) men’s. I had even tried adding more colors via lipstick which worked out well for a pop art maximalist like myself—but—I had still been reluctant to wear a dress. It felt like the final breach of gender nonconformity, a betrayal of my long-standing inner tomboy.

On September 18th, 2023, I spoke at a professional women’s conference in San Francisco for Women’s Declaration International, and I made it my mission to upgrade my look to a true adult woman’s aesthetic, in honor of my grownupnuss. I went to Goodwill to try on 50+ dresses, trying to find 1 or 2 that I vibed with, and was successful.

It wasn't just any dress; it was a symbol of transformation, a reflection of my evolving understanding of womanhood, and an embodiment of the journey I had embarked upon. The dress didn't hide my curves; it accentuated them. What I once perceived as vulnerabilities, I now saw as strengths. My female body, with its natural beauty, became something to celebrate, not to hide. The dress became a statement, not of conformity, but of embracing myself.

Later that evening, as I attended the opening reception of my art exhibition, I gazed at my self-portrait, Grace, displaying my mastectomy scars. Those scars were not marks of conformity; they were reminders of a chapter in my life when I had made choices driven by societal pressures and disconnection from divine biological reality. Walking through the gallery that night, I felt liberated. Wearing that dress wasn't just about clothing; it was about embracing my evolving understanding of womanhood. It was about celebrating the natural beauty of my female body, scars and all.

Grace encapsulates the tension between solipsistic mutilation, and existential beauty.

Empowerment comes from realizing one’s potential for higher evolution, not from conforming to fleeting external expectations.