I find it strange and a little funny when people comment on my fashion sense. I have no doubt that it’s genuinely praiseworthy, but some of the compliments I’ve received come with a little extra subtext I’d like to put to rest.
This fashion sense is the work of years, not months.
I’ve been paying vastly outsized attention to women’s clothing for my entire life. I’ve been able to render informed opinions on clothing styles and makeup hues since high school, if not earlier. I had weirdly specific ideas about what I wanted the women in my life to wear. I fantasized about and utterly failed to seduce partners who approximated that style in my misguided quest to surround myself with the precise sort of femininity that it turned out I actually wanted, not to be around, but to be. I did not face my more authentic clothing with the anxious confusion of an empty cistern. I turned that spigot and enough fashion came out to dress ten svelte Hispanic ladies. I was not intimidated by no longer being able to dejectedly match any T-shirt with one or another set of jeans and call it a day; I was liberated.
And because I came into this battle well-armed and, after an outpouring of support, well-provisioned, I’m sharing here what wisdom I have about how I look good in women’s clothing.