Safety and Risk while queering the gender normas
I have dresssed up en femme a few times now. I got my kit, my basic bag of clothing, from a few thrift stores. The ones in the richer neighborhoods have much nicer stuff.
I've got a few scarves. I've got a few skirts. Two sets of leggings. Two brassiers. Eyeglasses and masks get in the way but improve anonimity. I have not gone out while dressed up. I am fortunate that my significant other is radically accepting of it all.
In a perverse way, I feel calm and safer when I'm dressed en femme. I feel like I'm free of all the Toxic Masculinity bullshit I've been force-fed and had beaten into me since I was three years old. I feel a lot more comfortable dressed as feminine (in girl-mood, as Eddie Izzard says) and I feel heppy to be relived of all the male expectations. I'm much more comfortable with my feelings.
That's perverse because where I live, there's a great risk of significant violence when you're dressed as something unexpected. Don't challenge the local's sense of gender binary or their sense of defending the Creator's gender binary. And it goes downhill from there. I feel safer dressed up within my own head, but I'm definitely not safer dressed up as far as my community goes.
I've played dress-up before. I was in the military. They taught me to do things I didn't think possible. They motivated me to do things I thought I'd never do. They taught me a culture that helped me deal with death and safety and failure. A lot of it came because every day, I cleaned up and presented the image they taught me to, and wore their costume all day and night. And it helped me fit in, and it helped me succeed. But there's no doubt we were playing dress-up.