When I came out as a transgender woman, clothes were admittedly the last thing on my mind. There were (and continue to be) more pressing questions: legal and medical issues, documentation, hormones and relationships, to name just a handful. In fact, the thought of wearing female-identifying clothing was terrifying. Incredibly alluring, yes, but terrifying, too.

I have known since I was a young child that I didn’t feel “male” on the inside, but I had successfully avoided buying female-identifying clothing for 30 years. I’m not sure if this was due in part to my fear that giving in to temptation would result in me loving my female presentation too much to go back. Perhaps I was worried that I would be disappointed when I looked in the mirror; that I would feel less than perfect in my desired natural form as a woman. If perfection does exist, I thought, it was probably only in my mind’s closet. Better to dream of myself as a woman than see it in reality with the varnish stripped away.

If perfection does exist, I thought, it was probably only in my mind’s closet. Better to dream of myself as a woman than see it in reality with the varnish stripped away.

The weekend after I came out, one of my closest friends treated me to breakfast and surprised me with a shopping spree and style consultant. For the better part of a day, our little band hit up a half dozen stores to paint my body with various cuts and fabrics. I have a tall frame, an athletic build and a traditionally masculine face. A past girlfriend would occasionally tease me for a profile that might fit on an old Roman coin. And here I was, years later, attempting to discover my inner Aphrodite.

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Fashion, unsurprisingly, takes research. After some trial and error, we found sleeves that worked for my upper body — and decided plunging necklines were a bit too much to start. My legs — thank god — are just the right type of muscular and toned to look gorgeous in a sexy pencil skirt. Meanwhile, certain dresses betrayed my lack of an hourglass shape. Tops that were too sheer had an awkwardness that could not be saved by camisoles, much to my chagrin, but blouses with mandarin collars looked unusually flattering on my build.